id sid tid token lemma pos eurjchem-32 1 1 microsoft microsoft PROPN eurjchem-32 1 2 word word PROPN eurjchem-32 1 3 european_journal_of_chemistry_1_2_2010_90_95_32 european_journal_of_chemistry_1_2_2010_90_95_32 PROPN eurjchem-32 1 4 european european PROPN eurjchem-32 1 5     SPACE eurjchem-32 1 6 journal journal NOUN eurjchem-32 1 7     SPACE eurjchem-32 1 8 of of ADP eurjchem-32 1 9     SPACE eurjchem-32 1 10 chemistry chemistry NOUN eurjchem-32 1 11     SPACE eurjchem-32 1 12 1 1 NUM eurjchem-32 1 13     SPACE eurjchem-32 1 14 ( ( PUNCT eurjchem-32 1 15 2 2 NUM eurjchem-32 1 16 ) ) PUNCT eurjchem-32 1 17     SPACE eurjchem-32 1 18 ( ( PUNCT eurjchem-32 1 19 2010 2010 NUM eurjchem-32 1 20 ) ) PUNCT eurjchem-32 1 21     SPACE eurjchem-32 1 22 90‐95 90‐95 NUM eurjchem-32 1 23         SPACE eurjchem-32 1 24 european european ADJ eurjchem-32 1 25     SPACE eurjchem-32 1 26 journal journal NOUN eurjchem-32 1 27     SPACE eurjchem-32 1 28 of of ADP eurjchem-32 1 29     SPACE eurjchem-32 1 30 chemistry chemistry NOUN eurjchem-32 1 31     SPACE eurjchem-32 1 32 issn issn VERB eurjchem-32 1 33     SPACE eurjchem-32 1 34 2153‐2249 2153‐2249 NUM eurjchem-32 1 35     SPACE eurjchem-32 1 36 ( ( PUNCT eurjchem-32 1 37 print print NOUN eurjchem-32 1 38 ) ) PUNCT eurjchem-32 1 39     SPACE eurjchem-32 1 40 / / SYM eurjchem-32 1 41     SPACE eurjchem-32 1 42 issn issn VERB eurjchem-32 1 43     SPACE eurjchem-32 1 44 2153‐2257 2153‐2257 NUM eurjchem-32 1 45     SPACE eurjchem-32 1 46 ( ( PUNCT eurjchem-32 1 47 online online ADJ eurjchem-32 1 48 ) ) PUNCT eurjchem-32 1 49     SPACE eurjchem-32 1 50   NOUN eurjchem-32 1 51     SPACE eurjchem-32 1 52 2010 2010 NUM eurjchem-32 1 53     SPACE eurjchem-32 1 54 eurjchem eurjchem NOUN eurjchem-32 1 55     SPACE eurjchem-32 1 56 doi:10.5155 doi:10.5155 NOUN eurjchem-32 1 57 / / SYM eurjchem-32 1 58 eurjchem.1.2.90‐95.32 eurjchem.1.2.90‐95.32 NOUN eurjchem-32 1 59                 SPACE eurjchem-32 1 60 european european ADJ eurjchem-32 1 61     SPACE eurjchem-32 1 62 journal journal NOUN eurjchem-32 1 63     SPACE eurjchem-32 1 64 of of ADP eurjchem-32 1 65     SPACE eurjchem-32 1 66 chemistry chemistry NOUN eurjchem-32 1 67     SPACE eurjchem-32 1 68 journal journal NOUN eurjchem-32 1 69     SPACE eurjchem-32 1 70 homepage homepage NOUN eurjchem-32 1 71 : : PUNCT eurjchem-32 1 72     SPACE eurjchem-32 1 73 www.eurjchem.com www.eurjchem.com NOUN eurjchem-32 1 74                     SPACE eurjchem-32 1 75 synthetic synthetic ADJ eurjchem-32 1 76     SPACE eurjchem-32 1 77 applications application NOUN eurjchem-32 1 78     SPACE eurjchem-32 1 79 of of ADP eurjchem-32 1 80     SPACE eurjchem-32 1 81 benzothiazole benzothiazole NOUN eurjchem-32 1 82     SPACE eurjchem-32 1 83 containing contain VERB eurjchem-32 1 84     SPACE eurjchem-32 1 85 cyanoacetyl cyanoacetyl NOUN eurjchem-32 1 86     SPACE eurjchem-32 1 87 group group NOUN eurjchem-32 1 88     SPACE eurjchem-32 1 89 ahmed ahmed PROPN eurjchem-32 1 90     SPACE eurjchem-32 1 91 ali ali PROPN eurjchem-32 1 92     SPACE eurjchem-32 1 93 faddaa faddaa NOUN eurjchem-32 1 94 , , PUNCT eurjchem-32 1 95     SPACE eurjchem-32 1 96 fathy fathy PROPN eurjchem-32 1 97     SPACE eurjchem-32 1 98 mohamed mohamed PROPN eurjchem-32 1 99     SPACE eurjchem-32 1 100 abdelrazekb abdelrazekb NOUN eurjchem-32 1 101 , , PUNCT eurjchem-32 1 102 * * SYM eurjchem-32 1 103 , , PUNCT eurjchem-32 1 104     SPACE eurjchem-32 1 105 khaled khale VERB eurjchem-32 1 106     SPACE eurjchem-32 1 107 samir samir PROPN eurjchem-32 1 108     SPACE eurjchem-32 1 109 mohameda mohameda ADJ eurjchem-32 1 110 , , PUNCT eurjchem-32 1 111       SPACE eurjchem-32 1 112 howayda howayda NOUN eurjchem-32 1 113     SPACE eurjchem-32 1 114 mohamed mohamed PROPN eurjchem-32 1 115     SPACE eurjchem-32 1 116 mostafa mostafa PROPN eurjchem-32 1 117     SPACE eurjchem-32 1 118 ghietha ghietha PROPN eurjchem-32 1 119     SPACE eurjchem-32 1 120 and and CCONJ eurjchem-32 1 121     SPACE eurjchem-32 1 122 hassan hassan PROPN eurjchem-32 1 123     SPACE eurjchem-32 1 124 ali ali PROPN eurjchem-32 1 125     SPACE eurjchem-32 1 126 etmana etmana PROPN eurjchem-32 1 127       SPACE eurjchem-32 1 128 a a DET eurjchem-32 1 129     SPACE eurjchem-32 1 130 chemistry chemistry NOUN eurjchem-32 1 131     SPACE eurjchem-32 1 132 department department NOUN eurjchem-32 1 133 , , PUNCT eurjchem-32 1 134     SPACE eurjchem-32 1 135 faculty faculty NOUN eurjchem-32 1 136     SPACE eurjchem-32 1 137 of of ADP eurjchem-32 1 138     SPACE eurjchem-32 1 139 science science NOUN eurjchem-32 1 140 , , PUNCT eurjchem-32 1 141     SPACE eurjchem-32 1 142 mansoura mansoura ADJ eurjchem-32 1 143     SPACE eurjchem-32 1 144 university university NOUN eurjchem-32 1 145 , , PUNCT eurjchem-32 1 146     SPACE eurjchem-32 1 147 mansoura mansoura NOUN eurjchem-32 1 148 , , PUNCT eurjchem-32 1 149     SPACE eurjchem-32 1 150 35516 35516 NUM eurjchem-32 1 151 , , PUNCT eurjchem-32 1 152     SPACE eurjchem-32 1 153 egypt egypt PROPN eurjchem-32 1 154     SPACE eurjchem-32 1 155 b b PROPN eurjchem-32 1 156     SPACE eurjchem-32 1 157 chemistry chemistry NOUN eurjchem-32 1 158     SPACE eurjchem-32 1 159 department department NOUN eurjchem-32 1 160 , , PUNCT eurjchem-32 1 161     SPACE eurjchem-32 1 162 faculty faculty NOUN eurjchem-32 1 163     SPACE eurjchem-32 1 164 of of ADP eurjchem-32 1 165     SPACE eurjchem-32 1 166 science science NOUN eurjchem-32 1 167 , , PUNCT eurjchem-32 1 168     SPACE eurjchem-32 1 169 cairo cairo PROPN eurjchem-32 1 170     SPACE eurjchem-32 1 171 university university PROPN eurjchem-32 1 172 , , PUNCT eurjchem-32 1 173     SPACE eurjchem-32 1 174 giza giza NOUN eurjchem-32 1 175 , , PUNCT eurjchem-32 1 176     SPACE eurjchem-32 1 177 12613 12613 NUM eurjchem-32 1 178 , , PUNCT eurjchem-32 1 179     SPACE eurjchem-32 1 180 egypt egypt PROPN eurjchem-32 1 181     SPACE eurjchem-32 1 182 * * PROPN eurjchem-32 1 183 corresponding corresponding ADJ eurjchem-32 1 184     SPACE eurjchem-32 1 185 author author NOUN eurjchem-32 1 186     SPACE eurjchem-32 1 187 at at ADP eurjchem-32 1 188 : : PUNCT eurjchem-32 1 189     SPACE eurjchem-32 1 190 chemistry chemistry NOUN eurjchem-32 1 191     SPACE eurjchem-32 1 192 department department NOUN eurjchem-32 1 193 , , PUNCT eurjchem-32 1 194     SPACE eurjchem-32 1 195 faculty faculty NOUN eurjchem-32 1 196     SPACE eurjchem-32 1 197 of of ADP eurjchem-32 1 198     SPACE eurjchem-32 1 199 science science NOUN eurjchem-32 1 200 , , PUNCT eurjchem-32 1 201     SPACE eurjchem-32 1 202 cairo cairo PROPN eurjchem-32 1 203     SPACE eurjchem-32 1 204 university university PROPN eurjchem-32 1 205 , , PUNCT eurjchem-32 1 206     SPACE eurjchem-32 1 207 giza giza NOUN eurjchem-32 1 208 , , PUNCT eurjchem-32 1 209     SPACE eurjchem-32 1 210 12613 12613 NUM eurjchem-32 1 211 , , PUNCT eurjchem-32 1 212     SPACE eurjchem-32 1 213 egypt egypt PROPN eurjchem-32 1 214 . . PUNCT eurjchem-32 1 215     SPACE eurjchem-32 1 216 tel tel PROPN eurjchem-32 1 217 . . PUNCT eurjchem-32 1 218 : : PUNCT eurjchem-32 1 219     SPACE eurjchem-32 1 220 +202.35676601 +202.35676601 PROPN eurjchem-32 1 221 ; ; PUNCT eurjchem-32 1 222     SPACE eurjchem-32 1 223 fax fax NOUN eurjchem-32 1 224 : : PUNCT eurjchem-32 1 225     SPACE eurjchem-32 1 226 +202.35727556 +202.35727556 PROPN eurjchem-32 1 227 . . PUNCT eurjchem-32 1 228     SPACE eurjchem-32 1 229 e­mail e­mail NOUN eurjchem-32 1 230     SPACE eurjchem-32 1 231 address address NOUN eurjchem-32 1 232 : : PUNCT eurjchem-32 1 233     SPACE eurjchem-32 1 234 prof.fmrazek@gmail.com prof.fmrazek@gmail.com PROPN eurjchem-32 1 235       SPACE eurjchem-32 1 236 ( ( PUNCT eurjchem-32 1 237 f.m f.m PROPN eurjchem-32 1 238 . . PROPN eurjchem-32 1 239     SPACE eurjchem-32 1 240 abdelrazek abdelrazek NOUN eurjchem-32 1 241 ) ) PUNCT eurjchem-32 1 242 . . PUNCT eurjchem-32 1 243                                 SPACE eurjchem-32 1 244 article article NOUN eurjchem-32 1 245     SPACE eurjchem-32 1 246 information information NOUN eurjchem-32 1 247         SPACE eurjchem-32 1 248 abstract abstract ADJ eurjchem-32 1 249 received receive VERB eurjchem-32 1 250 : : PUNCT eurjchem-32 1 251     SPACE eurjchem-32 1 252 2 2 NUM eurjchem-32 1 253     SPACE eurjchem-32 1 254 april april PROPN eurjchem-32 1 255     SPACE eurjchem-32 1 256 2010 2010 NUM eurjchem-32 1 257     SPACE eurjchem-32 1 258 received receive VERB eurjchem-32 1 259     SPACE eurjchem-32 1 260 in in ADP eurjchem-32 1 261     SPACE eurjchem-32 1 262 revised revise VERB eurjchem-32 1 263     SPACE eurjchem-32 1 264 form form NOUN eurjchem-32 1 265 : : PUNCT eurjchem-32 1 266     SPACE eurjchem-32 1 267 14 14 NUM eurjchem-32 1 268     SPACE eurjchem-32 1 269 april april PROPN eurjchem-32 1 270     SPACE eurjchem-32 1 271 2010 2010 NUM eurjchem-32 1 272     SPACE eurjchem-32 1 273 accepted accept VERB eurjchem-32 1 274 : : PUNCT eurjchem-32 1 275     SPACE eurjchem-32 1 276 14 14 NUM eurjchem-32 1 277     SPACE eurjchem-32 1 278 april april PROPN eurjchem-32 1 279     SPACE eurjchem-32 1 280 2010 2010 NUM eurjchem-32 1 281     SPACE eurjchem-32 1 282 online online NOUN eurjchem-32 1 283 : : PUNCT eurjchem-32 1 284     SPACE eurjchem-32 1 285 30 30 NUM eurjchem-32 1 286     SPACE eurjchem-32 1 287 june june PROPN eurjchem-32 1 288     SPACE eurjchem-32 1 289 2010 2010 NUM eurjchem-32 1 290     SPACE eurjchem-32 1 291 keywords keyword VERB eurjchem-32 1 292         SPACE eurjchem-32 1 293 the the DET eurjchem-32 1 294     SPACE eurjchem-32 1 295 reactions reaction NOUN eurjchem-32 1 296     SPACE eurjchem-32 1 297 of of ADP eurjchem-32 1 298     SPACE eurjchem-32 1 299 2‐(benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile 2‐(benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile NOUN eurjchem-32 1 300     SPACE eurjchem-32 1 301 with with ADP eurjchem-32 1 302     SPACE eurjchem-32 1 303 a a DET eurjchem-32 1 304     SPACE eurjchem-32 1 305 variety variety NOUN eurjchem-32 1 306     SPACE eurjchem-32 1 307 of of ADP eurjchem-32 1 308     SPACE eurjchem-32 1 309 reagents reagent NOUN eurjchem-32 1 310     SPACE eurjchem-32 1 311 have have AUX eurjchem-32 1 312     SPACE eurjchem-32 1 313 been be AUX eurjchem-32 1 314     SPACE eurjchem-32 1 315 investigated investigate VERB eurjchem-32 1 316     SPACE eurjchem-32 1 317 aiming aiming NOUN eurjchem-32 1 318     SPACE eurjchem-32 1 319 to to PART eurjchem-32 1 320     SPACE eurjchem-32 1 321 explore explore VERB eurjchem-32 1 322     SPACE eurjchem-32 1 323 the the DET eurjchem-32 1 324     SPACE eurjchem-32 1 325 synthetic synthetic ADJ eurjchem-32 1 326     SPACE eurjchem-32 1 327 potentialities potentiality NOUN eurjchem-32 1 328     SPACE eurjchem-32 1 329 of of ADP eurjchem-32 1 330     SPACE eurjchem-32 1 331 this this DET eurjchem-32 1 332     SPACE eurjchem-32 1 333 activated activate VERB eurjchem-32 1 334     SPACE eurjchem-32 1 335 nitrile nitrile NOUN eurjchem-32 1 336     SPACE eurjchem-32 1 337 in in ADP eurjchem-32 1 338     SPACE eurjchem-32 1 339 heterocyclic heterocyclic ADJ eurjchem-32 1 340     SPACE eurjchem-32 1 341 synthesis synthesis NOUN eurjchem-32 1 342 . . PUNCT eurjchem-32 1 343     SPACE eurjchem-32 1 344 several several ADJ eurjchem-32 1 345     SPACE eurjchem-32 1 346 novel novel NOUN eurjchem-32 1 347     SPACE eurjchem-32 1 348 pyridopyrimidine pyridopyrimidine NOUN eurjchem-32 1 349 , , PUNCT eurjchem-32 1 350     SPACE eurjchem-32 1 351 chromenopyridine chromenopyridine NOUN eurjchem-32 1 352 , , PUNCT eurjchem-32 1 353     SPACE eurjchem-32 1 354 oxazole oxazole NOUN eurjchem-32 1 355 , , PUNCT eurjchem-32 1 356     SPACE eurjchem-32 1 357 diazepinone diazepinone PROPN eurjchem-32 1 358 , , PUNCT eurjchem-32 1 359     SPACE eurjchem-32 1 360 thiophene thiophene NOUN eurjchem-32 1 361     SPACE eurjchem-32 1 362 and and CCONJ eurjchem-32 1 363     SPACE eurjchem-32 1 364 thienopyridine thienopyridine NOUN eurjchem-32 1 365     SPACE eurjchem-32 1 366 derivatives derivative NOUN eurjchem-32 1 367     SPACE eurjchem-32 1 368 could could AUX eurjchem-32 1 369     SPACE eurjchem-32 1 370 be be AUX eurjchem-32 1 371     SPACE eurjchem-32 1 372 obtained obtain VERB eurjchem-32 1 373     SPACE eurjchem-32 1 374 starting start VERB eurjchem-32 1 375     SPACE eurjchem-32 1 376 from from ADP eurjchem-32 1 377     SPACE eurjchem-32 1 378 2‐ 2‐ NUM eurjchem-32 1 379 ( ( PUNCT eurjchem-32 1 380 benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile NOUN eurjchem-32 1 381     SPACE eurjchem-32 1 382 and and CCONJ eurjchem-32 1 383     SPACE eurjchem-32 1 384 plausible plausible ADJ eurjchem-32 1 385     SPACE eurjchem-32 1 386 mechanisms mechanism NOUN eurjchem-32 1 387     SPACE eurjchem-32 1 388 for for ADP eurjchem-32 1 389     SPACE eurjchem-32 1 390 their their PRON eurjchem-32 1 391     SPACE eurjchem-32 1 392 formations formation NOUN eurjchem-32 1 393     SPACE eurjchem-32 1 394 are be AUX eurjchem-32 1 395     SPACE eurjchem-32 1 396 reported report VERB eurjchem-32 1 397 . . PUNCT eurjchem-32 1 398     SPACE eurjchem-32 1 399 benzothiazole benzothiazole PROPN eurjchem-32 1 400     SPACE eurjchem-32 1 401 pyridopyrimidine pyridopyrimidine NOUN eurjchem-32 1 402     SPACE eurjchem-32 1 403 thienopyridine thienopyridine NOUN eurjchem-32 1 404     SPACE eurjchem-32 1 405 oxazole oxazole NOUN eurjchem-32 1 406     SPACE eurjchem-32 1 407 chromenopyridine chromenopyridine NOUN eurjchem-32 1 408     SPACE eurjchem-32 1 409 diazepinone diazepinone NOUN eurjchem-32 1 410     SPACE eurjchem-32 1 411 derivatives derivative NOUN eurjchem-32 1 412         SPACE eurjchem-32 1 413 1 1 NUM eurjchem-32 1 414 . . PUNCT eurjchem-32 1 415     SPACE eurjchem-32 1 416 introduction introduction NOUN eurjchem-32 1 417         SPACE eurjchem-32 1 418 thiazoles thiazole NOUN eurjchem-32 1 419     SPACE eurjchem-32 1 420 and and CCONJ eurjchem-32 1 421     SPACE eurjchem-32 1 422 benzothiazole benzothiazole NOUN eurjchem-32 1 423     SPACE eurjchem-32 1 424 derivatives derivative NOUN eurjchem-32 1 425     SPACE eurjchem-32 1 426 represent represent VERB eurjchem-32 1 427     SPACE eurjchem-32 1 428 a a DET eurjchem-32 1 429     SPACE eurjchem-32 1 430 well well ADV eurjchem-32 1 431     SPACE eurjchem-32 1 432 known know VERB eurjchem-32 1 433     SPACE eurjchem-32 1 434 important important ADJ eurjchem-32 1 435     SPACE eurjchem-32 1 436 group group NOUN eurjchem-32 1 437     SPACE eurjchem-32 1 438 of of ADP eurjchem-32 1 439     SPACE eurjchem-32 1 440 heterocyclic heterocyclic NOUN eurjchem-32 1 441     SPACE eurjchem-32 1 442 compounds compound VERB eurjchem-32 1 443     SPACE eurjchem-32 1 444 due due ADJ eurjchem-32 1 445     SPACE eurjchem-32 1 446 to to ADP eurjchem-32 1 447     SPACE eurjchem-32 1 448 their their PRON eurjchem-32 1 449     SPACE eurjchem-32 1 450 biological biological NOUN eurjchem-32 1 451     SPACE eurjchem-32 1 452 and and CCONJ eurjchem-32 1 453     SPACE eurjchem-32 1 454 pharmaceutical pharmaceutical NOUN eurjchem-32 1 455     SPACE eurjchem-32 1 456 activities activity NOUN eurjchem-32 1 457 . . PUNCT eurjchem-32 1 458     SPACE eurjchem-32 2 1 thus thus ADV eurjchem-32 2 2     SPACE eurjchem-32 2 3 many many ADJ eurjchem-32 2 4     SPACE eurjchem-32 2 5 diverse diverse ADJ eurjchem-32 2 6     SPACE eurjchem-32 2 7 biological biological ADJ eurjchem-32 2 8     SPACE eurjchem-32 2 9 activities activity NOUN eurjchem-32 2 10     SPACE eurjchem-32 2 11 such such ADJ eurjchem-32 2 12     SPACE eurjchem-32 2 13 as as ADP eurjchem-32 2 14     SPACE eurjchem-32 2 15 bactericidal bactericidal ADJ eurjchem-32 2 16 , , PUNCT eurjchem-32 2 17     SPACE eurjchem-32 2 18 pesticidal pesticidal NOUN eurjchem-32 2 19 , , PUNCT eurjchem-32 2 20     SPACE eurjchem-32 2 21 fungicidal fungicidal NOUN eurjchem-32 2 22 , , PUNCT eurjchem-32 2 23     SPACE eurjchem-32 2 24 insecticidal insecticidal NOUN eurjchem-32 2 25 , , PUNCT eurjchem-32 2 26     SPACE eurjchem-32 2 27 anticonvulsant anticonvulsant ADJ eurjchem-32 2 28 , , PUNCT eurjchem-32 2 29     SPACE eurjchem-32 2 30 tuberculostatic tuberculostatic ADJ eurjchem-32 2 31 , , PUNCT eurjchem-32 2 32     SPACE eurjchem-32 2 33 anti‐inflammatory anti‐inflammatory NOUN eurjchem-32 2 34 , , PUNCT eurjchem-32 2 35     SPACE eurjchem-32 2 36 and and CCONJ eurjchem-32 2 37     SPACE eurjchem-32 2 38 antithyroidal antithyroidal NOUN eurjchem-32 2 39     SPACE eurjchem-32 2 40 have have AUX eurjchem-32 2 41     SPACE eurjchem-32 2 42 been be AUX eurjchem-32 2 43     SPACE eurjchem-32 2 44 found find VERB eurjchem-32 2 45     SPACE eurjchem-32 2 46 to to PART eurjchem-32 2 47     SPACE eurjchem-32 2 48 be be AUX eurjchem-32 2 49     SPACE eurjchem-32 2 50 associated associate VERB eurjchem-32 2 51     SPACE eurjchem-32 2 52 with with ADP eurjchem-32 2 53     SPACE eurjchem-32 2 54 thiazole thiazole NOUN eurjchem-32 2 55     SPACE eurjchem-32 2 56 and and CCONJ eurjchem-32 2 57     SPACE eurjchem-32 2 58 benzothiazole benzothiazole NOUN eurjchem-32 2 59     SPACE eurjchem-32 2 60 derivatives derivative NOUN eurjchem-32 2 61 . . PUNCT eurjchem-32 2 62     SPACE eurjchem-32 3 1 benzothiazoles benzothiazole NOUN eurjchem-32 3 2     SPACE eurjchem-32 3 3 with with ADP eurjchem-32 3 4     SPACE eurjchem-32 3 5 a a DET eurjchem-32 3 6     SPACE eurjchem-32 3 7 cyanomethyl cyanomethyl NOUN eurjchem-32 3 8     SPACE eurjchem-32 3 9 group group NOUN eurjchem-32 3 10     SPACE eurjchem-32 3 11 at at ADP eurjchem-32 3 12     SPACE eurjchem-32 3 13 position‐2 position‐2 VERB eurjchem-32 3 14     SPACE eurjchem-32 3 15 have have AUX eurjchem-32 3 16     SPACE eurjchem-32 3 17 been be AUX eurjchem-32 3 18     SPACE eurjchem-32 3 19 the the DET eurjchem-32 3 20     SPACE eurjchem-32 3 21 subject subject NOUN eurjchem-32 3 22     SPACE eurjchem-32 3 23 of of ADP eurjchem-32 3 24     SPACE eurjchem-32 3 25 extensive extensive ADJ eurjchem-32 3 26     SPACE eurjchem-32 3 27 study study NOUN eurjchem-32 3 28     SPACE eurjchem-32 3 29 in in ADP eurjchem-32 3 30     SPACE eurjchem-32 3 31 the the DET eurjchem-32 3 32     SPACE eurjchem-32 3 33 recent recent ADJ eurjchem-32 3 34     SPACE eurjchem-32 3 35 past past NOUN eurjchem-32 3 36 . . PUNCT eurjchem-32 3 37     SPACE eurjchem-32 3 38 numerous numerous ADJ eurjchem-32 3 39     SPACE eurjchem-32 3 40 reports report NOUN eurjchem-32 3 41     SPACE eurjchem-32 3 42 have have AUX eurjchem-32 3 43     SPACE eurjchem-32 3 44 appeared appear VERB eurjchem-32 3 45     SPACE eurjchem-32 3 46 in in ADP eurjchem-32 3 47     SPACE eurjchem-32 3 48 the the DET eurjchem-32 3 49     SPACE eurjchem-32 3 50 literature literature NOUN eurjchem-32 3 51 , , PUNCT eurjchem-32 3 52     SPACE eurjchem-32 3 53 which which PRON eurjchem-32 3 54     SPACE eurjchem-32 3 55 highlight highlight VERB eurjchem-32 3 56     SPACE eurjchem-32 3 57 their their PRON eurjchem-32 3 58     SPACE eurjchem-32 3 59 chemistry chemistry NOUN eurjchem-32 3 60     SPACE eurjchem-32 3 61 and and CCONJ eurjchem-32 3 62     SPACE eurjchem-32 3 63 uses use NOUN eurjchem-32 3 64 . . PUNCT eurjchem-32 3 65     SPACE eurjchem-32 4 1 however however ADV eurjchem-32 4 2 , , PUNCT eurjchem-32 4 3     SPACE eurjchem-32 4 4 heterocycles heterocycle NOUN eurjchem-32 4 5     SPACE eurjchem-32 4 6 containing contain VERB eurjchem-32 4 7     SPACE eurjchem-32 4 8 cyanoacetyl cyanoacetyl NOUN eurjchem-32 4 9     SPACE eurjchem-32 4 10 group group NOUN eurjchem-32 4 11     SPACE eurjchem-32 4 12 are be AUX eurjchem-32 4 13     SPACE eurjchem-32 4 14 relatively relatively ADV eurjchem-32 4 15     SPACE eurjchem-32 4 16 unexplored unexplored ADJ eurjchem-32 4 17 , , PUNCT eurjchem-32 4 18     SPACE eurjchem-32 4 19 probably probably ADV eurjchem-32 4 20     SPACE eurjchem-32 4 21 because because SCONJ eurjchem-32 4 22     SPACE eurjchem-32 4 23 their their PRON eurjchem-32 4 24     SPACE eurjchem-32 4 25 preparation preparation NOUN eurjchem-32 4 26     SPACE eurjchem-32 4 27 involves involve VERB eurjchem-32 4 28     SPACE eurjchem-32 4 29 displacement displacement NOUN eurjchem-32 4 30     SPACE eurjchem-32 4 31 of of ADP eurjchem-32 4 32     SPACE eurjchem-32 4 33 the the DET eurjchem-32 4 34     SPACE eurjchem-32 4 35 halide halide NOUN eurjchem-32 4 36     SPACE eurjchem-32 4 37 in in ADP eurjchem-32 4 38     SPACE eurjchem-32 4 39 halo‐acetyl halo‐acetyl NOUN eurjchem-32 4 40     SPACE eurjchem-32 4 41 substituted substitute VERB eurjchem-32 4 42     SPACE eurjchem-32 4 43 heterocycles heterocycle NOUN eurjchem-32 4 44     SPACE eurjchem-32 4 45 with with ADP eurjchem-32 4 46     SPACE eurjchem-32 4 47 e.g. e.g. ADJ eurjchem-32 4 48     SPACE eurjchem-32 4 49 cyanide cyanide NOUN eurjchem-32 4 50     SPACE eurjchem-32 4 51 ion ion NOUN eurjchem-32 4 52     SPACE eurjchem-32 5 1 [ [ X eurjchem-32 5 2 1 1 NUM eurjchem-32 5 3 ] ] PUNCT eurjchem-32 5 4 , , PUNCT eurjchem-32 5 5     SPACE eurjchem-32 5 6 or or CCONJ eurjchem-32 5 7     SPACE eurjchem-32 5 8 from from ADP eurjchem-32 5 9     SPACE eurjchem-32 5 10 an an DET eurjchem-32 5 11     SPACE eurjchem-32 5 12 alkyl alkyl ADJ eurjchem-32 5 13     SPACE eurjchem-32 5 14 carboxylate carboxylate NOUN eurjchem-32 5 15     SPACE eurjchem-32 5 16 using use VERB eurjchem-32 5 17     SPACE eurjchem-32 5 18 acetonitrile acetonitrile NOUN eurjchem-32 5 19     SPACE eurjchem-32 5 20 in in ADP eurjchem-32 5 21     SPACE eurjchem-32 5 22 the the DET eurjchem-32 5 23     SPACE eurjchem-32 5 24 presence presence NOUN eurjchem-32 5 25     SPACE eurjchem-32 5 26 of of ADP eurjchem-32 5 27     SPACE eurjchem-32 5 28 a a DET eurjchem-32 5 29     SPACE eurjchem-32 5 30 strong strong ADJ eurjchem-32 5 31     SPACE eurjchem-32 5 32 base base NOUN eurjchem-32 5 33     SPACE eurjchem-32 5 34 like like ADP eurjchem-32 5 35     SPACE eurjchem-32 5 36 sodium sodium NOUN eurjchem-32 5 37     SPACE eurjchem-32 5 38 amide amide NOUN eurjchem-32 5 39     SPACE eurjchem-32 5 40 which which PRON eurjchem-32 5 41     SPACE eurjchem-32 5 42 usually usually ADV eurjchem-32 5 43     SPACE eurjchem-32 5 44 afforded afford VERB eurjchem-32 5 45     SPACE eurjchem-32 5 46 low low ADJ eurjchem-32 5 47     SPACE eurjchem-32 5 48 yields yield NOUN eurjchem-32 5 49     SPACE eurjchem-32 5 50 of of ADP eurjchem-32 5 51     SPACE eurjchem-32 5 52 impure impure NOUN eurjchem-32 5 53     SPACE eurjchem-32 5 54 products product NOUN eurjchem-32 5 55     SPACE eurjchem-32 6 1 [ [ X eurjchem-32 6 2 2 2 NUM eurjchem-32 6 3 ] ] PUNCT eurjchem-32 6 4 . . PUNCT eurjchem-32 6 5     SPACE eurjchem-32 6 6 acetyl acetyl NOUN eurjchem-32 6 7     SPACE eurjchem-32 6 8 chloride chloride NOUN eurjchem-32 6 9     SPACE eurjchem-32 6 10 itself itself PRON eurjchem-32 6 11     SPACE eurjchem-32 6 12 is be AUX eurjchem-32 6 13     SPACE eurjchem-32 6 14 not not PART eurjchem-32 6 15     SPACE eurjchem-32 6 16 particularly particularly ADV eurjchem-32 6 17     SPACE eurjchem-32 6 18 useful useful ADJ eurjchem-32 6 19     SPACE eurjchem-32 6 20 in in ADP eurjchem-32 6 21     SPACE eurjchem-32 6 22 this this DET eurjchem-32 6 23     SPACE eurjchem-32 6 24 respect respect NOUN eurjchem-32 6 25     SPACE eurjchem-32 6 26 since since SCONJ eurjchem-32 6 27     SPACE eurjchem-32 6 28 it it PRON eurjchem-32 6 29     SPACE eurjchem-32 6 30 undergoes undergo VERB eurjchem-32 6 31     SPACE eurjchem-32 6 32 dimerization dimerization NOUN eurjchem-32 6 33     SPACE eurjchem-32 6 34 [ [ X eurjchem-32 6 35 3 3 NUM eurjchem-32 6 36 ] ] PUNCT eurjchem-32 6 37 . . PUNCT eurjchem-32 6 38     SPACE eurjchem-32 6 39 cyanoacetylation cyanoacetylation NOUN eurjchem-32 6 40     SPACE eurjchem-32 6 41 of of ADP eurjchem-32 6 42     SPACE eurjchem-32 6 43 uracils uracil NOUN eurjchem-32 6 44     SPACE eurjchem-32 6 45 or or CCONJ eurjchem-32 6 46     SPACE eurjchem-32 6 47 their their PRON eurjchem-32 6 48     SPACE eurjchem-32 6 49 derivatives derivative NOUN eurjchem-32 6 50     SPACE eurjchem-32 7 1 [ [ X eurjchem-32 7 2 4‐6 4‐6 PROPN eurjchem-32 7 3 ] ] X eurjchem-32 7 4     SPACE eurjchem-32 7 5 and and CCONJ eurjchem-32 7 6     SPACE eurjchem-32 7 7 enamines enamine NOUN eurjchem-32 7 8     SPACE eurjchem-32 7 9 [ [ X eurjchem-32 7 10 7 7 NUM eurjchem-32 7 11 ] ] PUNCT eurjchem-32 7 12     SPACE eurjchem-32 7 13 has have AUX eurjchem-32 7 14     SPACE eurjchem-32 7 15 been be AUX eurjchem-32 7 16     SPACE eurjchem-32 7 17 reported report VERB eurjchem-32 7 18     SPACE eurjchem-32 7 19 to to PART eurjchem-32 7 20     SPACE eurjchem-32 7 21 be be AUX eurjchem-32 7 22     SPACE eurjchem-32 7 23 successfully successfully ADV eurjchem-32 7 24     SPACE eurjchem-32 7 25 achieved achieve VERB eurjchem-32 7 26     SPACE eurjchem-32 7 27 by by ADP eurjchem-32 7 28     SPACE eurjchem-32 7 29 heating heating NOUN eurjchem-32 7 30     SPACE eurjchem-32 7 31 the the DET eurjchem-32 7 32     SPACE eurjchem-32 7 33 respective respective ADJ eurjchem-32 7 34     SPACE eurjchem-32 7 35 substrate substrate NOUN eurjchem-32 7 36     SPACE eurjchem-32 7 37 with with ADP eurjchem-32 7 38     SPACE eurjchem-32 7 39 a a DET eurjchem-32 7 40     SPACE eurjchem-32 7 41 mixture mixture NOUN eurjchem-32 7 42     SPACE eurjchem-32 7 43 of of ADP eurjchem-32 7 44     SPACE eurjchem-32 7 45 acetic acetic ADJ eurjchem-32 7 46     SPACE eurjchem-32 7 47 anhydride anhydride NOUN eurjchem-32 7 48     SPACE eurjchem-32 7 49 and and CCONJ eurjchem-32 7 50     SPACE eurjchem-32 7 51 cyanoacetic cyanoacetic ADJ eurjchem-32 7 52     SPACE eurjchem-32 7 53 acid acid NOUN eurjchem-32 7 54     SPACE eurjchem-32 7 55 as as ADP eurjchem-32 7 56     SPACE eurjchem-32 7 57 a a DET eurjchem-32 7 58     SPACE eurjchem-32 7 59 cyano‐acetylating cyano‐acetylating ADJ eurjchem-32 7 60     SPACE eurjchem-32 7 61 mixture mixture NOUN eurjchem-32 7 62 . . PUNCT eurjchem-32 7 63     SPACE eurjchem-32 8 1 the the DET eurjchem-32 8 2     SPACE eurjchem-32 8 3 structure structure NOUN eurjchem-32 8 4     SPACE eurjchem-32 8 5 of of ADP eurjchem-32 8 6     SPACE eurjchem-32 8 7 the the DET eurjchem-32 8 8     SPACE eurjchem-32 8 9 reactive reactive NOUN eurjchem-32 8 10     SPACE eurjchem-32 8 11 species specie NOUN eurjchem-32 8 12     SPACE eurjchem-32 8 13 formed form VERB eurjchem-32 8 14     SPACE eurjchem-32 8 15 in in ADP eurjchem-32 8 16     SPACE eurjchem-32 8 17 this this DET eurjchem-32 8 18     SPACE eurjchem-32 8 19 case case NOUN eurjchem-32 8 20     SPACE eurjchem-32 8 21 has have AUX eurjchem-32 8 22     SPACE eurjchem-32 8 23 been be AUX eurjchem-32 8 24     SPACE eurjchem-32 8 25 assigned assign VERB eurjchem-32 8 26     SPACE eurjchem-32 8 27 as as ADP eurjchem-32 8 28     SPACE eurjchem-32 8 29 a a DET eurjchem-32 8 30     SPACE eurjchem-32 8 31 cyano‐ketene cyano‐ketene NOUN eurjchem-32 8 32 . . PUNCT eurjchem-32 8 33     SPACE eurjchem-32 9 1 the the DET eurjchem-32 9 2     SPACE eurjchem-32 9 3 use use NOUN eurjchem-32 9 4     SPACE eurjchem-32 9 5 of of ADP eurjchem-32 9 6     SPACE eurjchem-32 9 7 this this DET eurjchem-32 9 8     SPACE eurjchem-32 9 9 cyano‐ cyano‐ VERB eurjchem-32 9 10 acetylating acetylate VERB eurjchem-32 9 11     SPACE eurjchem-32 9 12 mixture mixture NOUN eurjchem-32 9 13     SPACE eurjchem-32 9 14 ( ( PUNCT eurjchem-32 9 15 cyanoacetic cyanoacetic ADJ eurjchem-32 9 16     SPACE eurjchem-32 9 17 acid acid NOUN eurjchem-32 9 18     SPACE eurjchem-32 9 19 and and CCONJ eurjchem-32 9 20     SPACE eurjchem-32 9 21 acetic acetic ADJ eurjchem-32 9 22     SPACE eurjchem-32 9 23 anhydride anhydride NOUN eurjchem-32 9 24 ) ) PUNCT eurjchem-32 9 25     SPACE eurjchem-32 9 26 has have AUX eurjchem-32 9 27     SPACE eurjchem-32 9 28 somehow somehow ADV eurjchem-32 9 29     SPACE eurjchem-32 9 30 been be AUX eurjchem-32 9 31     SPACE eurjchem-32 9 32 forgotten forget VERB eurjchem-32 9 33     SPACE eurjchem-32 9 34 and and CCONJ eurjchem-32 9 35     SPACE eurjchem-32 9 36 instead instead ADV eurjchem-32 9 37     SPACE eurjchem-32 9 38 other other ADJ eurjchem-32 9 39     SPACE eurjchem-32 9 40 less less ADJ eurjchem-32 9 41     SPACE eurjchem-32 9 42 convenient convenient ADJ eurjchem-32 9 43     SPACE eurjchem-32 9 44 reagents reagent NOUN eurjchem-32 9 45     SPACE eurjchem-32 9 46 like like ADP eurjchem-32 9 47     SPACE eurjchem-32 9 48 the the DET eurjchem-32 9 49     SPACE eurjchem-32 9 50 pyrrole pyrrole NOUN eurjchem-32 9 51     SPACE eurjchem-32 9 52 derivative derivative NOUN eurjchem-32 9 53     SPACE eurjchem-32 9 54 1 1 NUM eurjchem-32 9 55     SPACE eurjchem-32 9 56 has have AUX eurjchem-32 9 57     SPACE eurjchem-32 9 58 been be AUX eurjchem-32 9 59     SPACE eurjchem-32 9 60 used use VERB eurjchem-32 9 61     SPACE eurjchem-32 9 62 [ [ X eurjchem-32 9 63 8 8 NUM eurjchem-32 9 64 ] ] SYM eurjchem-32 9 65     SPACE eurjchem-32 9 66 ( ( PUNCT eurjchem-32 9 67 scheme scheme NOUN eurjchem-32 9 68     SPACE eurjchem-32 9 69 1 1 NUM eurjchem-32 9 70 ) ) PUNCT eurjchem-32 9 71 . . PUNCT eurjchem-32 9 72     SPACE eurjchem-32 10 1 the the DET eurjchem-32 10 2     SPACE eurjchem-32 10 3 phenolic phenolic NOUN eurjchem-32 10 4     SPACE eurjchem-32 10 5 ester ester NOUN eurjchem-32 10 6     SPACE eurjchem-32 10 7 2 2 NUM eurjchem-32 10 8     SPACE eurjchem-32 10 9 of of ADP eurjchem-32 10 10     SPACE eurjchem-32 10 11 cyanoacetic cyanoacetic ADJ eurjchem-32 10 12     SPACE eurjchem-32 10 13 acid acid NOUN eurjchem-32 10 14     SPACE eurjchem-32 10 15 is be AUX eurjchem-32 10 16     SPACE eurjchem-32 10 17 also also ADV eurjchem-32 10 18     SPACE eurjchem-32 10 19 suggested suggest VERB eurjchem-32 10 20     SPACE eurjchem-32 10 21 for for ADP eurjchem-32 10 22     SPACE eurjchem-32 10 23 cyano‐acetylation cyano‐acetylation NOUN eurjchem-32 10 24     SPACE eurjchem-32 10 25 since since SCONJ eurjchem-32 10 26     SPACE eurjchem-32 10 27 it it PRON eurjchem-32 10 28     SPACE eurjchem-32 10 29 generates generate VERB eurjchem-32 10 30     SPACE eurjchem-32 10 31 cyano‐ketene cyano‐ketene NOUN eurjchem-32 10 32     SPACE eurjchem-32 10 33 when when SCONJ eurjchem-32 10 34     SPACE eurjchem-32 10 35 heated heat VERB eurjchem-32 10 36     SPACE eurjchem-32 10 37 [ [ X eurjchem-32 10 38 9 9 NUM eurjchem-32 10 39 ] ] PUNCT eurjchem-32 10 40 . . PUNCT eurjchem-32 10 41     SPACE eurjchem-32 10 42 in in ADP eurjchem-32 10 43     SPACE eurjchem-32 10 44 the the DET eurjchem-32 10 45     SPACE eurjchem-32 10 46 last last ADJ eurjchem-32 10 47     SPACE eurjchem-32 10 48 two two NUM eurjchem-32 10 49     SPACE eurjchem-32 10 50 decades decade NOUN eurjchem-32 10 51 , , PUNCT eurjchem-32 10 52     SPACE eurjchem-32 10 53 we we PRON eurjchem-32 10 54     SPACE eurjchem-32 10 55 have have AUX eurjchem-32 10 56     SPACE eurjchem-32 10 57 been be AUX eurjchem-32 10 58     SPACE eurjchem-32 10 59 involved involve VERB eurjchem-32 10 60     SPACE eurjchem-32 10 61 in in ADP eurjchem-32 10 62     SPACE eurjchem-32 10 63 a a DET eurjchem-32 10 64     SPACE eurjchem-32 10 65 program program NOUN eurjchem-32 10 66     SPACE eurjchem-32 10 67 aiming aiming NOUN eurjchem-32 10 68     SPACE eurjchem-32 10 69 to to PART eurjchem-32 10 70     SPACE eurjchem-32 10 71 develop develop VERB eurjchem-32 10 72     SPACE eurjchem-32 10 73 new new ADJ eurjchem-32 10 74     SPACE eurjchem-32 10 75 simple simple ADJ eurjchem-32 10 76     SPACE eurjchem-32 10 77 procedures procedure NOUN eurjchem-32 10 78     SPACE eurjchem-32 10 79 or or CCONJ eurjchem-32 10 80     SPACE eurjchem-32 10 81 novel novel NOUN eurjchem-32 10 82     SPACE eurjchem-32 10 83 precursors precursor NOUN eurjchem-32 10 84     SPACE eurjchem-32 10 85 for for ADP eurjchem-32 10 86     SPACE eurjchem-32 10 87 the the DET eurjchem-32 10 88     SPACE eurjchem-32 10 89 synthesis synthesis NOUN eurjchem-32 10 90     SPACE eurjchem-32 10 91 of of ADP eurjchem-32 10 92     SPACE eurjchem-32 10 93 heterocyclic heterocyclic NOUN eurjchem-32 10 94     SPACE eurjchem-32 10 95 compounds compound NOUN eurjchem-32 10 96     SPACE eurjchem-32 10 97 of of ADP eurjchem-32 10 98     SPACE eurjchem-32 10 99 biological biological ADJ eurjchem-32 10 100     SPACE eurjchem-32 10 101 interest interest NOUN eurjchem-32 10 102     SPACE eurjchem-32 10 103 to to PART eurjchem-32 10 104     SPACE eurjchem-32 10 105 be be AUX eurjchem-32 10 106     SPACE eurjchem-32 10 107 evaluated evaluate VERB eurjchem-32 10 108     SPACE eurjchem-32 10 109 as as ADP eurjchem-32 10 110     SPACE eurjchem-32 10 111 biodegradable biodegradable ADJ eurjchem-32 10 112     SPACE eurjchem-32 10 113 agrochemicals agrochemical NOUN eurjchem-32 10 114     SPACE eurjchem-32 11 1 [ [ X eurjchem-32 11 2 10‐14 10‐14 NUM eurjchem-32 11 3 ] ] PUNCT eurjchem-32 11 4 . . PUNCT eurjchem-32 11 5     SPACE eurjchem-32 12 1 in in ADP eurjchem-32 12 2     SPACE eurjchem-32 12 3 continuation continuation NOUN eurjchem-32 12 4     SPACE eurjchem-32 12 5 with with ADP eurjchem-32 12 6     SPACE eurjchem-32 12 7 this this DET eurjchem-32 12 8     SPACE eurjchem-32 12 9 program program NOUN eurjchem-32 12 10     SPACE eurjchem-32 12 11 some some DET eurjchem-32 12 12     SPACE eurjchem-32 12 13 heterocyclic heterocyclic NOUN eurjchem-32 12 14     SPACE eurjchem-32 12 15 compounds compound NOUN eurjchem-32 12 16     SPACE eurjchem-32 12 17 containing contain VERB eurjchem-32 12 18     SPACE eurjchem-32 12 19 the the DET eurjchem-32 12 20     SPACE eurjchem-32 12 21 benzothiazole benzothiazole NOUN eurjchem-32 12 22     SPACE eurjchem-32 12 23 nucleus nucleus NOUN eurjchem-32 12 24     SPACE eurjchem-32 12 25 were be AUX eurjchem-32 12 26     SPACE eurjchem-32 12 27 required require VERB eurjchem-32 12 28     SPACE eurjchem-32 12 29 for for ADP eurjchem-32 12 30     SPACE eurjchem-32 12 31 biological biological ADJ eurjchem-32 12 32     SPACE eurjchem-32 12 33 activity activity NOUN eurjchem-32 12 34     SPACE eurjchem-32 12 35 studies study NOUN eurjchem-32 12 36 . . PUNCT eurjchem-32 12 37     SPACE eurjchem-32 13 1 2‐(benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile 2‐(benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile NUM eurjchem-32 13 2 , , PUNCT eurjchem-32 13 3     SPACE eurjchem-32 13 4 4 4 NUM eurjchem-32 13 5 , , PUNCT eurjchem-32 13 6     SPACE eurjchem-32 13 7 ( ( PUNCT eurjchem-32 13 8 obtained obtain VERB eurjchem-32 13 9     SPACE eurjchem-32 13 10 by by ADP eurjchem-32 13 11     SPACE eurjchem-32 13 12 cyano‐acetylation cyano‐acetylation NOUN eurjchem-32 13 13     SPACE eurjchem-32 13 14 of of ADP eurjchem-32 13 15     SPACE eurjchem-32 13 16 3 3 NUM eurjchem-32 13 17 ) ) PUNCT eurjchem-32 13 18     SPACE eurjchem-32 13 19 seemed seem VERB eurjchem-32 13 20     SPACE eurjchem-32 13 21 a a DET eurjchem-32 13 22     SPACE eurjchem-32 13 23 versatile versatile ADJ eurjchem-32 13 24     SPACE eurjchem-32 13 25 candidate candidate NOUN eurjchem-32 13 26     SPACE eurjchem-32 13 27 to to PART eurjchem-32 13 28     SPACE eurjchem-32 13 29 fulfill fulfill VERB eurjchem-32 13 30     SPACE eurjchem-32 13 31 this this DET eurjchem-32 13 32     SPACE eurjchem-32 13 33 objective objective NOUN eurjchem-32 13 34     SPACE eurjchem-32 13 35 ( ( PUNCT eurjchem-32 13 36 scheme scheme NOUN eurjchem-32 13 37     SPACE eurjchem-32 13 38 2 2 NUM eurjchem-32 13 39 ) ) PUNCT eurjchem-32 13 40 . . PUNCT eurjchem-32 13 41           SPACE eurjchem-32 14 1 scheme scheme NOUN eurjchem-32 14 2     SPACE eurjchem-32 14 3 1 1 NUM eurjchem-32 14 4         SPACE eurjchem-32 14 5 scheme scheme NOUN eurjchem-32 14 6     SPACE eurjchem-32 14 7 2 2 NUM eurjchem-32 14 8         SPACE eurjchem-32 14 9 2 2 NUM eurjchem-32 14 10 . . PUNCT eurjchem-32 14 11     SPACE eurjchem-32 14 12 experimental experimental ADJ eurjchem-32 14 13         SPACE eurjchem-32 14 14 all all DET eurjchem-32 14 15     SPACE eurjchem-32 14 16 melting melting NOUN eurjchem-32 14 17     SPACE eurjchem-32 14 18 points point NOUN eurjchem-32 14 19     SPACE eurjchem-32 14 20 are be AUX eurjchem-32 14 21     SPACE eurjchem-32 14 22 recorded record VERB eurjchem-32 14 23     SPACE eurjchem-32 14 24 on on ADP eurjchem-32 14 25     SPACE eurjchem-32 14 26 gallenkamp gallenkamp NOUN eurjchem-32 14 27     SPACE eurjchem-32 14 28 electric electric NOUN eurjchem-32 14 29     SPACE eurjchem-32 14 30 melting melting NOUN eurjchem-32 14 31     SPACE eurjchem-32 14 32 point point NOUN eurjchem-32 14 33     SPACE eurjchem-32 14 34 apparatus apparatus NOUN eurjchem-32 14 35 . . PUNCT eurjchem-32 14 36     SPACE eurjchem-32 15 1 the the DET eurjchem-32 15 2     SPACE eurjchem-32 15 3 ir ir PROPN eurjchem-32 15 4     SPACE eurjchem-32 15 5 spectra spectra NOUN eurjchem-32 15 6     SPACE eurjchem-32 15 7 υ υ NOUN eurjchem-32 15 8     SPACE eurjchem-32 15 9 ( ( PUNCT eurjchem-32 15 10 cm‐1 cm‐1 NOUN eurjchem-32 15 11 ) ) PUNCT eurjchem-32 15 12     SPACE eurjchem-32 15 13 ( ( PUNCT eurjchem-32 15 14 kbr kbr PROPN eurjchem-32 15 15 ) ) PUNCT eurjchem-32 15 16     SPACE eurjchem-32 15 17 were be AUX eurjchem-32 15 18     SPACE eurjchem-32 15 19 recorded record VERB eurjchem-32 15 20     SPACE eurjchem-32 15 21 on on ADP eurjchem-32 15 22     SPACE eurjchem-32 15 23 a a DET eurjchem-32 15 24     SPACE eurjchem-32 15 25 perkin perkin NOUN eurjchem-32 15 26     SPACE eurjchem-32 15 27 elmer elmer PROPN eurjchem-32 15 28     SPACE eurjchem-32 15 29 infrared infrare VERB eurjchem-32 15 30     SPACE eurjchem-32 15 31 spectrophotometer spectrophotometer NOUN eurjchem-32 15 32     SPACE eurjchem-32 15 33 model model NOUN eurjchem-32 15 34     SPACE eurjchem-32 15 35 157 157 NUM eurjchem-32 15 36 . . PUNCT eurjchem-32 15 37     SPACE eurjchem-32 15 38 the the DET eurjchem-32 15 39     SPACE eurjchem-32 15 40 1h 1h NUM eurjchem-32 15 41     SPACE eurjchem-32 15 42 nmr nmr NOUN eurjchem-32 15 43     SPACE eurjchem-32 15 44 spectra spectra NOUN eurjchem-32 15 45     SPACE eurjchem-32 15 46 were be AUX eurjchem-32 15 47     SPACE eurjchem-32 15 48 obtained obtain VERB eurjchem-32 15 49     SPACE eurjchem-32 15 50 on on ADP eurjchem-32 15 51     SPACE eurjchem-32 15 52 a a DET eurjchem-32 15 53     SPACE eurjchem-32 15 54 varian varian NOUN eurjchem-32 15 55     SPACE eurjchem-32 15 56 spectrophotometer spectrophotometer NOUN eurjchem-32 15 57     SPACE eurjchem-32 15 58 at at ADP eurjchem-32 15 59     SPACE eurjchem-32 15 60 200 200 NUM eurjchem-32 15 61     SPACE eurjchem-32 15 62 mhz mhz NOUN eurjchem-32 15 63 , , PUNCT eurjchem-32 15 64     SPACE eurjchem-32 15 65 using use VERB eurjchem-32 15 66     SPACE eurjchem-32 15 67 tms tms NOUN eurjchem-32 15 68     SPACE eurjchem-32 15 69 as as ADP eurjchem-32 15 70     SPACE eurjchem-32 15 71 an an DET eurjchem-32 15 72     SPACE eurjchem-32 15 73 internal internal ADJ eurjchem-32 15 74     SPACE eurjchem-32 15 75 reference reference NOUN eurjchem-32 15 76     SPACE eurjchem-32 15 77 and and CCONJ eurjchem-32 15 78     SPACE eurjchem-32 15 79 dmso‐d6 dmso‐d6 NOUN eurjchem-32 15 80     SPACE eurjchem-32 15 81 as as ADP eurjchem-32 15 82     SPACE eurjchem-32 15 83 solvent solvent NOUN eurjchem-32 15 84 . . PUNCT eurjchem-32 15 85     SPACE eurjchem-32 16 1 the the DET eurjchem-32 16 2     SPACE eurjchem-32 16 3 13c 13c NOUN eurjchem-32 16 4     SPACE eurjchem-32 16 5 nmr nmr NOUN eurjchem-32 16 6     SPACE eurjchem-32 16 7 spectra spectra NOUN eurjchem-32 16 8     SPACE eurjchem-32 16 9 were be AUX eurjchem-32 16 10     SPACE eurjchem-32 16 11 recorded record VERB eurjchem-32 16 12     SPACE eurjchem-32 16 13 on on ADP eurjchem-32 16 14     SPACE eurjchem-32 16 15 jeol‐eca500 jeol‐eca500 PROPN eurjchem-32 16 16     SPACE eurjchem-32 16 17 ( ( PUNCT eurjchem-32 16 18 national national ADJ eurjchem-32 16 19     SPACE eurjchem-32 16 20 research research NOUN eurjchem-32 16 21     SPACE eurjchem-32 16 22 center center NOUN eurjchem-32 16 23 , , PUNCT eurjchem-32 16 24     SPACE eurjchem-32 16 25 egypt egypt PROPN eurjchem-32 16 26 ) ) PUNCT eurjchem-32 16 27 . . PUNCT eurjchem-32 16 28     SPACE eurjchem-32 17 1 fadda fadda PROPN eurjchem-32 17 2     SPACE eurjchem-32 17 3 et et PROPN eurjchem-32 17 4     SPACE eurjchem-32 17 5 al al PROPN eurjchem-32 17 6 . . PROPN eurjchem-32 17 7     SPACE eurjchem-32 17 8 / / SYM eurjchem-32 17 9     SPACE eurjchem-32 17 10 european european ADJ eurjchem-32 17 11     SPACE eurjchem-32 17 12 journal journal NOUN eurjchem-32 17 13     SPACE eurjchem-32 17 14 of of ADP eurjchem-32 17 15     SPACE eurjchem-32 17 16 chemistry chemistry NOUN eurjchem-32 17 17     SPACE eurjchem-32 17 18 1 1 NUM eurjchem-32 17 19     SPACE eurjchem-32 17 20 ( ( PUNCT eurjchem-32 17 21 2 2 NUM eurjchem-32 17 22 ) ) PUNCT eurjchem-32 17 23     SPACE eurjchem-32 17 24 ( ( PUNCT eurjchem-32 17 25 2010 2010 NUM eurjchem-32 17 26 ) ) PUNCT eurjchem-32 17 27     SPACE eurjchem-32 18 1 90­95 90­95 NUM eurjchem-32 18 2     SPACE eurjchem-32 18 3 91 91 NUM eurjchem-32 18 4     SPACE eurjchem-32 18 5 the the DET eurjchem-32 18 6     SPACE eurjchem-32 18 7 mass mass PROPN eurjchem-32 18 8     SPACE eurjchem-32 18 9 spectra spectra NOUN eurjchem-32 18 10     SPACE eurjchem-32 18 11 ( ( PUNCT eurjchem-32 18 12 ei ei NOUN eurjchem-32 18 13 ) ) PUNCT eurjchem-32 18 14     SPACE eurjchem-32 18 15 were be AUX eurjchem-32 18 16     SPACE eurjchem-32 18 17 recorded record VERB eurjchem-32 18 18     SPACE eurjchem-32 18 19 at at ADP eurjchem-32 18 20     SPACE eurjchem-32 18 21 70 70 NUM eurjchem-32 18 22     SPACE eurjchem-32 18 23 ev ev NOUN eurjchem-32 18 24     SPACE eurjchem-32 18 25 with with ADP eurjchem-32 18 26     SPACE eurjchem-32 18 27 kratos kratos PROPN eurjchem-32 18 28     SPACE eurjchem-32 18 29 ms ms PROPN eurjchem-32 18 30     SPACE eurjchem-32 18 31 equipment equipment NOUN eurjchem-32 18 32     SPACE eurjchem-32 18 33 and/or and/or CCONJ eurjchem-32 18 34     SPACE eurjchem-32 18 35 a a DET eurjchem-32 18 36     SPACE eurjchem-32 18 37 varian varian NOUN eurjchem-32 18 38     SPACE eurjchem-32 18 39 mat mat NOUN eurjchem-32 18 40     SPACE eurjchem-32 18 41 311 311 NUM eurjchem-32 18 42     SPACE eurjchem-32 18 43 a a DET eurjchem-32 18 44     SPACE eurjchem-32 18 45 spectrometer spectrometer NOUN eurjchem-32 18 46 . . PUNCT eurjchem-32 18 47     SPACE eurjchem-32 19 1 elemental elemental NOUN eurjchem-32 19 2     SPACE eurjchem-32 19 3 analyses analysis NOUN eurjchem-32 19 4     SPACE eurjchem-32 19 5 ( ( PUNCT eurjchem-32 19 6 c c X eurjchem-32 19 7 , , PUNCT eurjchem-32 19 8     SPACE eurjchem-32 19 9 h h NOUN eurjchem-32 19 10     SPACE eurjchem-32 19 11 and and CCONJ eurjchem-32 19 12     SPACE eurjchem-32 19 13 n n CCONJ eurjchem-32 19 14 ) ) PUNCT eurjchem-32 19 15     SPACE eurjchem-32 19 16 were be AUX eurjchem-32 19 17     SPACE eurjchem-32 19 18 carried carry VERB eurjchem-32 19 19     SPACE eurjchem-32 19 20 out out ADP eurjchem-32 19 21     SPACE eurjchem-32 19 22 at at ADP eurjchem-32 19 23     SPACE eurjchem-32 19 24 the the DET eurjchem-32 19 25     SPACE eurjchem-32 19 26 micro micro NOUN eurjchem-32 19 27     SPACE eurjchem-32 19 28 analytical analytical ADJ eurjchem-32 19 29     SPACE eurjchem-32 19 30 center center NOUN eurjchem-32 19 31     SPACE eurjchem-32 19 32 of of ADP eurjchem-32 19 33     SPACE eurjchem-32 19 34 cairo cairo PROPN eurjchem-32 19 35     SPACE eurjchem-32 19 36 univ univ PROPN eurjchem-32 19 37 . . PROPN eurjchem-32 19 38 , , PUNCT eurjchem-32 19 39     SPACE eurjchem-32 19 40 giza giza PROPN eurjchem-32 19 41 , , PUNCT eurjchem-32 19 42     SPACE eurjchem-32 19 43 egypt egypt PROPN eurjchem-32 19 44 . . PUNCT eurjchem-32 19 45         SPACE eurjchem-32 19 46 2.1 2.1 NUM eurjchem-32 19 47 . . PUNCT eurjchem-32 19 48     SPACE eurjchem-32 20 1 2­(benzo[d]thiazol­2­yl)­3­oxopentanedinitrile 2­(benzo[d]thiazol­2­yl)­3­oxopentanedinitrile NUM eurjchem-32 20 2 , , PUNCT eurjchem-32 20 3     SPACE eurjchem-32 20 4 4 4 NUM eurjchem-32 20 5           SPACE eurjchem-32 20 6 to to ADP eurjchem-32 20 7     SPACE eurjchem-32 20 8 a a DET eurjchem-32 20 9     SPACE eurjchem-32 20 10 solution solution NOUN eurjchem-32 20 11     SPACE eurjchem-32 20 12 of of ADP eurjchem-32 20 13     SPACE eurjchem-32 20 14 cyanoacetic cyanoacetic ADJ eurjchem-32 20 15     SPACE eurjchem-32 20 16 acid acid NOUN eurjchem-32 20 17     SPACE eurjchem-32 20 18 ( ( PUNCT eurjchem-32 20 19 0.85 0.85 NUM eurjchem-32 20 20     SPACE eurjchem-32 20 21 g g NOUN eurjchem-32 20 22 , , PUNCT eurjchem-32 20 23     SPACE eurjchem-32 20 24 0.01 0.01 NUM eurjchem-32 20 25     SPACE eurjchem-32 20 26 mol mol NOUN eurjchem-32 20 27 ) ) PUNCT eurjchem-32 20 28     SPACE eurjchem-32 20 29 and and CCONJ eurjchem-32 20 30     SPACE eurjchem-32 20 31 acetic acetic ADJ eurjchem-32 20 32     SPACE eurjchem-32 20 33 anhydride anhydride NOUN eurjchem-32 20 34     SPACE eurjchem-32 20 35 ( ( PUNCT eurjchem-32 20 36 15 15 NUM eurjchem-32 20 37     SPACE eurjchem-32 20 38 ml ml NOUN eurjchem-32 20 39 ) ) PUNCT eurjchem-32 20 40     SPACE eurjchem-32 20 41 that that PRON eurjchem-32 20 42     SPACE eurjchem-32 20 43 was be AUX eurjchem-32 20 44     SPACE eurjchem-32 20 45 heated heated ADJ eurjchem-32 20 46     SPACE eurjchem-32 20 47 on on ADP eurjchem-32 20 48     SPACE eurjchem-32 20 49 water water NOUN eurjchem-32 20 50     SPACE eurjchem-32 20 51 bath bath NOUN eurjchem-32 20 52     SPACE eurjchem-32 20 53 for for ADP eurjchem-32 20 54     SPACE eurjchem-32 20 55 5 5 NUM eurjchem-32 20 56     SPACE eurjchem-32 20 57 min min NOUN eurjchem-32 20 58     SPACE eurjchem-32 20 59 , , PUNCT eurjchem-32 20 60     SPACE eurjchem-32 20 61 2‐(benzo[d]thiazol‐2‐yl)acetonitrile 2‐(benzo[d]thiazol‐2‐yl)acetonitrile NUM eurjchem-32 20 62     SPACE eurjchem-32 20 63 ( ( PUNCT eurjchem-32 20 64 3 3 NUM eurjchem-32 20 65 ) ) PUNCT eurjchem-32 20 66     SPACE eurjchem-32 20 67 ( ( PUNCT eurjchem-32 20 68 1.74 1.74 NUM eurjchem-32 20 69     SPACE eurjchem-32 20 70 g g NOUN eurjchem-32 20 71 , , PUNCT eurjchem-32 20 72     SPACE eurjchem-32 20 73 0.01 0.01 NUM eurjchem-32 20 74     SPACE eurjchem-32 20 75 mol mol NOUN eurjchem-32 20 76 ) ) PUNCT eurjchem-32 20 77     SPACE eurjchem-32 20 78 was be AUX eurjchem-32 20 79     SPACE eurjchem-32 20 80 added add VERB eurjchem-32 20 81     SPACE eurjchem-32 20 82 and and CCONJ eurjchem-32 20 83     SPACE eurjchem-32 20 84 the the DET eurjchem-32 20 85     SPACE eurjchem-32 20 86 reaction reaction NOUN eurjchem-32 20 87     SPACE eurjchem-32 20 88 mixture mixture NOUN eurjchem-32 20 89     SPACE eurjchem-32 20 90 was be AUX eurjchem-32 20 91     SPACE eurjchem-32 20 92 refluxed refluxe VERB eurjchem-32 20 93     SPACE eurjchem-32 20 94 for for ADP eurjchem-32 20 95     SPACE eurjchem-32 20 96 20 20 NUM eurjchem-32 20 97     SPACE eurjchem-32 20 98 min min NOUN eurjchem-32 20 99     SPACE eurjchem-32 20 100 at at ADP eurjchem-32 20 101     SPACE eurjchem-32 20 102 85‐95 85‐95 NOUN eurjchem-32 20 103     SPACE eurjchem-32 20 104 oc oc PROPN eurjchem-32 20 105 . . PROPN eurjchem-32 20 106     SPACE eurjchem-32 20 107 left leave VERB eurjchem-32 20 108     SPACE eurjchem-32 20 109 to to PART eurjchem-32 20 110     SPACE eurjchem-32 20 111 cool cool ADJ eurjchem-32 20 112 , , PUNCT eurjchem-32 20 113     SPACE eurjchem-32 20 114 and and CCONJ eurjchem-32 20 115     SPACE eurjchem-32 20 116 the the DET eurjchem-32 20 117     SPACE eurjchem-32 20 118 formed form VERB eurjchem-32 20 119     SPACE eurjchem-32 20 120 solid solid NOUN eurjchem-32 20 121     SPACE eurjchem-32 20 122 was be AUX eurjchem-32 20 123     SPACE eurjchem-32 20 124 filtered filter VERB eurjchem-32 20 125     SPACE eurjchem-32 20 126 off off ADP eurjchem-32 20 127 , , PUNCT eurjchem-32 20 128     SPACE eurjchem-32 20 129 dried dry VERB eurjchem-32 20 130     SPACE eurjchem-32 20 131 and and CCONJ eurjchem-32 20 132     SPACE eurjchem-32 20 133 recrystallized recrystallize VERB eurjchem-32 20 134     SPACE eurjchem-32 20 135 from from ADP eurjchem-32 20 136     SPACE eurjchem-32 20 137 ethanol ethanol NOUN eurjchem-32 20 138     SPACE eurjchem-32 20 139 to to PART eurjchem-32 20 140     SPACE eurjchem-32 20 141 afford afford VERB eurjchem-32 20 142     SPACE eurjchem-32 20 143 1.69 1.69 NUM eurjchem-32 20 144     SPACE eurjchem-32 20 145 g g NOUN eurjchem-32 20 146     SPACE eurjchem-32 20 147 ( ( PUNCT eurjchem-32 20 148 70 70 NUM eurjchem-32 20 149 % % NOUN eurjchem-32 20 150 ) ) PUNCT eurjchem-32 20 151     SPACE eurjchem-32 20 152 of of ADP eurjchem-32 20 153     SPACE eurjchem-32 20 154 4 4 NUM eurjchem-32 20 155 ; ; PUNCT eurjchem-32 20 156     SPACE eurjchem-32 20 157 mp mp NOUN eurjchem-32 20 158     SPACE eurjchem-32 20 159 275 275 NUM eurjchem-32 20 160     SPACE eurjchem-32 20 161 oc oc NOUN eurjchem-32 20 162 ; ; PUNCT eurjchem-32 20 163     SPACE eurjchem-32 20 164 brown brown ADJ eurjchem-32 20 165     SPACE eurjchem-32 20 166 crystals crystal NOUN eurjchem-32 20 167 ; ; PUNCT eurjchem-32 20 168     SPACE eurjchem-32 20 169 ir ir PROPN eurjchem-32 20 170     SPACE eurjchem-32 20 171 ( ( PUNCT eurjchem-32 20 172 kbr kbr PROPN eurjchem-32 20 173 ) ) PUNCT eurjchem-32 20 174     SPACE eurjchem-32 20 175 ( ( PUNCT eurjchem-32 20 176 υ υ NOUN eurjchem-32 20 177 , , PUNCT eurjchem-32 20 178     SPACE eurjchem-32 20 179 cm‐1 cm‐1 NOUN eurjchem-32 20 180 ): ): PUNCT eurjchem-32 20 181     SPACE eurjchem-32 20 182 2185 2185 NUM eurjchem-32 20 183 , , PUNCT eurjchem-32 20 184     SPACE eurjchem-32 20 185 2199 2199 NUM eurjchem-32 20 186     SPACE eurjchem-32 20 187 ( ( PUNCT eurjchem-32 20 188 2cn 2cn ADJ eurjchem-32 20 189 ) ) PUNCT eurjchem-32 20 190 , , PUNCT eurjchem-32 20 191     SPACE eurjchem-32 20 192 1700 1700 NUM eurjchem-32 20 193     SPACE eurjchem-32 20 194 ( ( PUNCT eurjchem-32 20 195 co co NOUN eurjchem-32 20 196 ) ) PUNCT eurjchem-32 20 197 . . PUNCT eurjchem-32 20 198     SPACE eurjchem-32 21 1 1h 1h NUM eurjchem-32 21 2     SPACE eurjchem-32 21 3 nmr nmr NOUN eurjchem-32 21 4     SPACE eurjchem-32 21 5 ( ( PUNCT eurjchem-32 21 6 dmso‐d6 dmso‐d6 NOUN eurjchem-32 21 7 ): ): PUNCT eurjchem-32 21 8     SPACE eurjchem-32 21 9 δ δ PROPN eurjchem-32 21 10 , , PUNCT eurjchem-32 21 11     SPACE eurjchem-32 21 12 4.52 4.52 NUM eurjchem-32 21 13     SPACE eurjchem-32 21 14 ( ( PUNCT eurjchem-32 21 15 s s PROPN eurjchem-32 21 16 , , PUNCT eurjchem-32 21 17     SPACE eurjchem-32 21 18 2h 2h NUM eurjchem-32 21 19 , , PUNCT eurjchem-32 21 20     SPACE eurjchem-32 21 21 ch2 ch2 PROPN eurjchem-32 21 22 ) ) PUNCT eurjchem-32 21 23 , , PUNCT eurjchem-32 21 24     SPACE eurjchem-32 21 25 5.10 5.10 NUM eurjchem-32 21 26     SPACE eurjchem-32 21 27 ( ( PUNCT eurjchem-32 21 28 s s PROPN eurjchem-32 21 29 , , PUNCT eurjchem-32 21 30     SPACE eurjchem-32 21 31 1h 1h NUM eurjchem-32 21 32 , , PUNCT eurjchem-32 21 33     SPACE eurjchem-32 21 34 ch ch NOUN eurjchem-32 21 35 ) ) PUNCT eurjchem-32 21 36 , , PUNCT eurjchem-32 21 37     SPACE eurjchem-32 21 38 6.67‐7.50 6.67‐7.50 NUM eurjchem-32 21 39     SPACE eurjchem-32 21 40 ( ( PUNCT eurjchem-32 21 41 m m PROPN eurjchem-32 21 42 , , PUNCT eurjchem-32 21 43     SPACE eurjchem-32 21 44 5h 5h NUM eurjchem-32 21 45 , , PUNCT eurjchem-32 21 46     SPACE eurjchem-32 21 47 ar‐h ar‐h NOUN eurjchem-32 21 48 ) ) PUNCT eurjchem-32 21 49 . . PUNCT eurjchem-32 21 50     SPACE eurjchem-32 22 1 ms ms NOUN eurjchem-32 22 2 : : PUNCT eurjchem-32 22 3     SPACE eurjchem-32 22 4 ( ( PUNCT eurjchem-32 22 5 m m PROPN eurjchem-32 22 6 / / SYM eurjchem-32 22 7 z z NOUN eurjchem-32 22 8 , , PUNCT eurjchem-32 22 9     SPACE eurjchem-32 22 10 % % NOUN eurjchem-32 22 11 ): ): PUNCT eurjchem-32 22 12     SPACE eurjchem-32 22 13 241 241 NUM eurjchem-32 22 14     SPACE eurjchem-32 22 15 ( ( PUNCT eurjchem-32 22 16 m+ m+ NUM eurjchem-32 22 17 , , PUNCT eurjchem-32 22 18     SPACE eurjchem-32 22 19 36.8 36.8 NUM eurjchem-32 22 20 ) ) PUNCT eurjchem-32 22 21 , , PUNCT eurjchem-32 22 22     SPACE eurjchem-32 22 23 201 201 NUM eurjchem-32 22 24     SPACE eurjchem-32 22 25 ( ( PUNCT eurjchem-32 22 26 m+‐ch2cn m+‐ch2cn PROPN eurjchem-32 22 27 , , PUNCT eurjchem-32 22 28     SPACE eurjchem-32 22 29 100.0 100.0 NUM eurjchem-32 22 30 ) ) PUNCT eurjchem-32 22 31 , , PUNCT eurjchem-32 22 32     SPACE eurjchem-32 22 33 173 173 NUM eurjchem-32 22 34     SPACE eurjchem-32 22 35 ( ( PUNCT eurjchem-32 22 36 m+‐coch2cn m+‐coch2cn PROPN eurjchem-32 22 37 , , PUNCT eurjchem-32 22 38     SPACE eurjchem-32 22 39 20.8 20.8 NUM eurjchem-32 22 40 ) ) PUNCT eurjchem-32 22 41 , , PUNCT eurjchem-32 22 42     SPACE eurjchem-32 22 43 146 146 NUM eurjchem-32 22 44     SPACE eurjchem-32 22 45 ( ( PUNCT eurjchem-32 22 46 40.3 40.3 NUM eurjchem-32 22 47 ) ) PUNCT eurjchem-32 22 48 , , PUNCT eurjchem-32 22 49     SPACE eurjchem-32 22 50 108 108 NUM eurjchem-32 22 51     SPACE eurjchem-32 22 52 ( ( PUNCT eurjchem-32 22 53 21.5 21.5 NUM eurjchem-32 22 54 ) ) PUNCT eurjchem-32 22 55 , , PUNCT eurjchem-32 22 56     SPACE eurjchem-32 22 57 69 69 NUM eurjchem-32 22 58     SPACE eurjchem-32 22 59 ( ( PUNCT eurjchem-32 22 60 84.7 84.7 NUM eurjchem-32 22 61 ) ) PUNCT eurjchem-32 22 62 . . PUNCT eurjchem-32 22 63     SPACE eurjchem-32 23 1 anal anal ADJ eurjchem-32 23 2 . . PUNCT eurjchem-32 23 3     SPACE eurjchem-32 23 4 calcd calcd NOUN eurjchem-32 23 5 . . PUNCT eurjchem-32 23 6     SPACE eurjchem-32 23 7 for for ADP eurjchem-32 23 8     SPACE eurjchem-32 23 9 c12h7n3os c12h7n3os NOUN eurjchem-32 23 10 : : PUNCT eurjchem-32 23 11     SPACE eurjchem-32 23 12 c c X eurjchem-32 23 13 , , PUNCT eurjchem-32 23 14     SPACE eurjchem-32 23 15 59.74 59.74 NUM eurjchem-32 23 16 ; ; PUNCT eurjchem-32 23 17     SPACE eurjchem-32 23 18 h h NOUN eurjchem-32 23 19 , , PUNCT eurjchem-32 23 20     SPACE eurjchem-32 23 21 2.92 2.92 NUM eurjchem-32 23 22 ; ; PUNCT eurjchem-32 23 23     SPACE eurjchem-32 23 24 n n CCONJ eurjchem-32 23 25 , , PUNCT eurjchem-32 23 26     SPACE eurjchem-32 23 27 17.42 17.42 NUM eurjchem-32 23 28 . . PUNCT eurjchem-32 23 29     SPACE eurjchem-32 23 30 found find VERB eurjchem-32 23 31 : : PUNCT eurjchem-32 23 32     SPACE eurjchem-32 23 33 c c X eurjchem-32 23 34 , , PUNCT eurjchem-32 23 35     SPACE eurjchem-32 23 36 59.92 59.92 NUM eurjchem-32 23 37 ; ; PUNCT eurjchem-32 23 38     SPACE eurjchem-32 23 39 h h NOUN eurjchem-32 23 40 , , PUNCT eurjchem-32 23 41     SPACE eurjchem-32 23 42 2.97 2.97 NUM eurjchem-32 23 43 ; ; PUNCT eurjchem-32 23 44     SPACE eurjchem-32 23 45 n n CCONJ eurjchem-32 23 46 , , PUNCT eurjchem-32 23 47     SPACE eurjchem-32 23 48 17.53 17.53 NUM eurjchem-32 23 49 . . PUNCT eurjchem-32 23 50         SPACE eurjchem-32 23 51 2.2 2.2 NUM eurjchem-32 23 52 . . PUNCT eurjchem-32 23 53     SPACE eurjchem-32 23 54 2­(benzo[d]thiazol­2­yl)­3­(4­chlorophenyl)­ 2­(benzo[d]thiazol­2­yl)­3­(4­chlorophenyl)­ NUM eurjchem-32 23 55 acrylonitrile acrylonitrile NOUN eurjchem-32 23 56 , , PUNCT eurjchem-32 23 57     SPACE eurjchem-32 23 58 5 5 NUM eurjchem-32 23 59               SPACE eurjchem-32 23 60 to to ADP eurjchem-32 23 61     SPACE eurjchem-32 23 62 a a DET eurjchem-32 23 63     SPACE eurjchem-32 23 64 solution solution NOUN eurjchem-32 23 65     SPACE eurjchem-32 23 66 of of ADP eurjchem-32 23 67     SPACE eurjchem-32 23 68 4 4 NUM eurjchem-32 23 69     SPACE eurjchem-32 23 70 ( ( PUNCT eurjchem-32 23 71 2.41 2.41 NUM eurjchem-32 23 72     SPACE eurjchem-32 23 73 g g NOUN eurjchem-32 23 74 , , PUNCT eurjchem-32 23 75     SPACE eurjchem-32 23 76 0.01 0.01 NUM eurjchem-32 23 77     SPACE eurjchem-32 23 78 mol mol NOUN eurjchem-32 23 79 ) ) PUNCT eurjchem-32 23 80     SPACE eurjchem-32 23 81 and and CCONJ eurjchem-32 23 82     SPACE eurjchem-32 23 83 p‐ p‐ NOUN eurjchem-32 23 84 chlorobenzaldehyde chlorobenzaldehyde NOUN eurjchem-32 23 85     SPACE eurjchem-32 23 86 ( ( PUNCT eurjchem-32 23 87 1.41 1.41 NUM eurjchem-32 23 88     SPACE eurjchem-32 23 89 g g NOUN eurjchem-32 23 90 , , PUNCT eurjchem-32 23 91     SPACE eurjchem-32 23 92 0.01 0.01 NUM eurjchem-32 23 93     SPACE eurjchem-32 23 94 mol mol NOUN eurjchem-32 23 95 ) ) PUNCT eurjchem-32 23 96     SPACE eurjchem-32 23 97 in in ADP eurjchem-32 23 98     SPACE eurjchem-32 23 99 ethanol ethanol NOUN eurjchem-32 23 100     SPACE eurjchem-32 23 101 ( ( PUNCT eurjchem-32 23 102 20 20 NUM eurjchem-32 23 103     SPACE eurjchem-32 23 104 ml ml NOUN eurjchem-32 23 105 ) ) PUNCT eurjchem-32 23 106 , , PUNCT eurjchem-32 23 107     SPACE eurjchem-32 23 108 was be AUX eurjchem-32 23 109     SPACE eurjchem-32 23 110 added add VERB eurjchem-32 23 111     SPACE eurjchem-32 23 112 a a DET eurjchem-32 23 113     SPACE eurjchem-32 23 114 few few ADJ eurjchem-32 23 115     SPACE eurjchem-32 23 116 drops drop VERB eurjchem-32 23 117     SPACE eurjchem-32 23 118 of of ADP eurjchem-32 23 119     SPACE eurjchem-32 23 120 piperidine piperidine NOUN eurjchem-32 23 121     SPACE eurjchem-32 23 122 and and CCONJ eurjchem-32 23 123     SPACE eurjchem-32 23 124 the the DET eurjchem-32 23 125     SPACE eurjchem-32 23 126 reaction reaction NOUN eurjchem-32 23 127     SPACE eurjchem-32 23 128 mixture mixture NOUN eurjchem-32 23 129     SPACE eurjchem-32 23 130 was be AUX eurjchem-32 23 131     SPACE eurjchem-32 23 132 refluxed refluxe VERB eurjchem-32 23 133     SPACE eurjchem-32 23 134 for for ADP eurjchem-32 23 135     SPACE eurjchem-32 23 136 4 4 NUM eurjchem-32 23 137     SPACE eurjchem-32 23 138 h h NOUN eurjchem-32 23 139 , , PUNCT eurjchem-32 23 140     SPACE eurjchem-32 23 141 then then ADV eurjchem-32 23 142     SPACE eurjchem-32 23 143 left leave VERB eurjchem-32 23 144     SPACE eurjchem-32 23 145 to to PART eurjchem-32 23 146     SPACE eurjchem-32 23 147 cool cool VERB eurjchem-32 23 148     SPACE eurjchem-32 23 149 ( ( PUNCT eurjchem-32 23 150 scheme scheme NOUN eurjchem-32 23 151     SPACE eurjchem-32 23 152 3 3 NUM eurjchem-32 23 153 ) ) PUNCT eurjchem-32 23 154 . . PUNCT eurjchem-32 23 155     SPACE eurjchem-32 24 1 the the DET eurjchem-32 24 2     SPACE eurjchem-32 24 3 precipitate precipitate NOUN eurjchem-32 24 4     SPACE eurjchem-32 24 5 that that PRON eurjchem-32 24 6     SPACE eurjchem-32 24 7 formed form VERB eurjchem-32 24 8     SPACE eurjchem-32 24 9 was be AUX eurjchem-32 24 10     SPACE eurjchem-32 24 11 filtered filter VERB eurjchem-32 24 12     SPACE eurjchem-32 24 13 off off ADP eurjchem-32 24 14 , , PUNCT eurjchem-32 24 15     SPACE eurjchem-32 24 16 washed wash VERB eurjchem-32 24 17     SPACE eurjchem-32 24 18 with with ADP eurjchem-32 24 19     SPACE eurjchem-32 24 20 ethanol ethanol NOUN eurjchem-32 24 21     SPACE eurjchem-32 24 22 and and CCONJ eurjchem-32 24 23     SPACE eurjchem-32 24 24 purified purify VERB eurjchem-32 24 25     SPACE eurjchem-32 24 26 by by SCONJ eurjchem-32 24 27     SPACE eurjchem-32 24 28 recrystallized recrystallize VERB eurjchem-32 24 29     SPACE eurjchem-32 24 30 from from ADP eurjchem-32 24 31     SPACE eurjchem-32 24 32 ethanol ethanol NOUN eurjchem-32 24 33     SPACE eurjchem-32 24 34 to to PART eurjchem-32 24 35     SPACE eurjchem-32 24 36 afford afford VERB eurjchem-32 24 37     SPACE eurjchem-32 24 38 2.11 2.11 NUM eurjchem-32 24 39     SPACE eurjchem-32 24 40 g g NOUN eurjchem-32 24 41     SPACE eurjchem-32 24 42 ( ( PUNCT eurjchem-32 24 43 71 71 NUM eurjchem-32 24 44 % % NOUN eurjchem-32 24 45 ) ) PUNCT eurjchem-32 24 46     SPACE eurjchem-32 24 47 of of ADP eurjchem-32 24 48     SPACE eurjchem-32 24 49 5 5 NUM eurjchem-32 24 50 ; ; PUNCT eurjchem-32 24 51     SPACE eurjchem-32 24 52 mp mp NOUN eurjchem-32 24 53     SPACE eurjchem-32 24 54 > > NOUN eurjchem-32 24 55     SPACE eurjchem-32 24 56 300 300 NUM eurjchem-32 24 57     SPACE eurjchem-32 24 58 oc oc NOUN eurjchem-32 24 59 ; ; PUNCT eurjchem-32 24 60     SPACE eurjchem-32 24 61 yellow yellow ADJ eurjchem-32 24 62     SPACE eurjchem-32 24 63 powder powder NOUN eurjchem-32 24 64 ; ; PUNCT eurjchem-32 24 65     SPACE eurjchem-32 24 66 ir ir PROPN eurjchem-32 24 67     SPACE eurjchem-32 24 68 ( ( PUNCT eurjchem-32 24 69 kbr kbr PROPN eurjchem-32 24 70 ) ) PUNCT eurjchem-32 24 71     SPACE eurjchem-32 24 72 ( ( PUNCT eurjchem-32 24 73 υ υ NOUN eurjchem-32 24 74 , , PUNCT eurjchem-32 24 75     SPACE eurjchem-32 24 76 cm‐1 cm‐1 NOUN eurjchem-32 24 77 ): ): PUNCT eurjchem-32 24 78         SPACE eurjchem-32 24 79 3119 3119 NUM eurjchem-32 24 80     SPACE eurjchem-32 24 81 ( ( PUNCT eurjchem-32 24 82 nh nh NOUN eurjchem-32 24 83 ) ) PUNCT eurjchem-32 24 84 , , PUNCT eurjchem-32 24 85     SPACE eurjchem-32 24 86 2188 2188 NUM eurjchem-32 24 87     SPACE eurjchem-32 24 88 ( ( PUNCT eurjchem-32 24 89 cn cn PROPN eurjchem-32 24 90 ) ) PUNCT eurjchem-32 24 91 . . PUNCT eurjchem-32 24 92     SPACE eurjchem-32 24 93 1h 1h NUM eurjchem-32 24 94     SPACE eurjchem-32 24 95 nmr nmr NOUN eurjchem-32 24 96     SPACE eurjchem-32 24 97 ( ( PUNCT eurjchem-32 24 98 dmso‐d6 dmso‐d6 NOUN eurjchem-32 24 99 ): ): PUNCT eurjchem-32 24 100     SPACE eurjchem-32 24 101 δ δ PROPN eurjchem-32 24 102 , , PUNCT eurjchem-32 24 103     SPACE eurjchem-32 24 104 7.32‐8.12 7.32‐8.12 NOUN eurjchem-32 24 105     SPACE eurjchem-32 24 106 ( ( PUNCT eurjchem-32 24 107 m m PROPN eurjchem-32 24 108 , , PUNCT eurjchem-32 24 109     SPACE eurjchem-32 24 110 arom arom NOUN eurjchem-32 24 111 . . PUNCT eurjchem-32 24 112     SPACE eurjchem-32 25 1 + + ADJ eurjchem-32 25 2     SPACE eurjchem-32 25 3 vinylic vinylic ADJ eurjchem-32 25 4     SPACE eurjchem-32 25 5 h h NOUN eurjchem-32 25 6 ) ) PUNCT eurjchem-32 25 7 . . PUNCT eurjchem-32 25 8     SPACE eurjchem-32 26 1 ms ms NOUN eurjchem-32 26 2 : : PUNCT eurjchem-32 26 3     SPACE eurjchem-32 26 4 ( ( PUNCT eurjchem-32 26 5 m m PROPN eurjchem-32 26 6 / / SYM eurjchem-32 26 7 z z NOUN eurjchem-32 26 8 , , PUNCT eurjchem-32 26 9     SPACE eurjchem-32 26 10 % % NOUN eurjchem-32 26 11 ): ): PUNCT eurjchem-32 26 12     SPACE eurjchem-32 26 13 298 298 NUM eurjchem-32 26 14     SPACE eurjchem-32 26 15 ( ( PUNCT eurjchem-32 26 16 m+ m+ NOUN eurjchem-32 26 17     SPACE eurjchem-32 26 18 +1 +1 PROPN eurjchem-32 26 19 , , PUNCT eurjchem-32 26 20     SPACE eurjchem-32 26 21 3.8 3.8 NUM eurjchem-32 26 22 ) ) PUNCT eurjchem-32 26 23 , , PUNCT eurjchem-32 26 24     SPACE eurjchem-32 26 25 297 297 NUM eurjchem-32 26 26     SPACE eurjchem-32 26 27 ( ( PUNCT eurjchem-32 26 28 m+ m+ NUM eurjchem-32 26 29 , , PUNCT eurjchem-32 26 30     SPACE eurjchem-32 26 31 3.8 3.8 NUM eurjchem-32 26 32 ) ) PUNCT eurjchem-32 26 33 , , PUNCT eurjchem-32 26 34     SPACE eurjchem-32 26 35 259 259 NUM eurjchem-32 26 36     SPACE eurjchem-32 26 37 ( ( PUNCT eurjchem-32 26 38 4.4 4.4 NUM eurjchem-32 26 39 ) ) PUNCT eurjchem-32 26 40 , , PUNCT eurjchem-32 26 41     SPACE eurjchem-32 26 42 174 174 NUM eurjchem-32 26 43     SPACE eurjchem-32 26 44 ( ( PUNCT eurjchem-32 26 45 14.4 14.4 NUM eurjchem-32 26 46 ) ) PUNCT eurjchem-32 26 47 , , PUNCT eurjchem-32 26 48     SPACE eurjchem-32 26 49 125 125 NUM eurjchem-32 26 50     SPACE eurjchem-32 26 51 ( ( PUNCT eurjchem-32 26 52 20.0 20.0 NUM eurjchem-32 26 53 ) ) PUNCT eurjchem-32 26 54 , , PUNCT eurjchem-32 26 55     SPACE eurjchem-32 26 56 84 84 NUM eurjchem-32 26 57     SPACE eurjchem-32 26 58 ( ( PUNCT eurjchem-32 26 59 100.0 100.0 NUM eurjchem-32 26 60 ) ) PUNCT eurjchem-32 26 61 . . PUNCT eurjchem-32 26 62     SPACE eurjchem-32 27 1 anal anal ADJ eurjchem-32 27 2 . . PUNCT eurjchem-32 27 3     SPACE eurjchem-32 27 4 calcd calcd NOUN eurjchem-32 27 5 . . PUNCT eurjchem-32 27 6     SPACE eurjchem-32 28 1 for for ADP eurjchem-32 28 2     SPACE eurjchem-32 28 3 c16h9cln2s c16h9cln2s PROPN eurjchem-32 28 4 : : PUNCT eurjchem-32 28 5     SPACE eurjchem-32 28 6 c c X eurjchem-32 28 7 , , PUNCT eurjchem-32 28 8     SPACE eurjchem-32 28 9 64.75 64.75 NUM eurjchem-32 28 10 ; ; PUNCT eurjchem-32 28 11     SPACE eurjchem-32 28 12 h h NOUN eurjchem-32 28 13 , , PUNCT eurjchem-32 28 14     SPACE eurjchem-32 28 15 3.06 3.06 NUM eurjchem-32 28 16 ; ; PUNCT eurjchem-32 28 17     SPACE eurjchem-32 28 18 n n CCONJ eurjchem-32 28 19 , , PUNCT eurjchem-32 28 20     SPACE eurjchem-32 28 21 9.44 9.44 NUM eurjchem-32 28 22 . . PUNCT eurjchem-32 28 23     SPACE eurjchem-32 28 24 found find VERB eurjchem-32 28 25 : : PUNCT eurjchem-32 28 26     SPACE eurjchem-32 28 27 c c X eurjchem-32 28 28 , , PUNCT eurjchem-32 28 29     SPACE eurjchem-32 28 30 64.84 64.84 NUM eurjchem-32 28 31 ; ; PUNCT eurjchem-32 28 32     SPACE eurjchem-32 28 33 h h NOUN eurjchem-32 28 34 , , PUNCT eurjchem-32 28 35     SPACE eurjchem-32 28 36 3.17 3.17 NUM eurjchem-32 28 37 ; ; PUNCT eurjchem-32 28 38     SPACE eurjchem-32 28 39 n n CCONJ eurjchem-32 28 40 , , PUNCT eurjchem-32 28 41     SPACE eurjchem-32 28 42 9.51 9.51 NUM eurjchem-32 28 43 . . PUNCT eurjchem-32 28 44         SPACE eurjchem-32 28 45 scheme scheme NOUN eurjchem-32 28 46     SPACE eurjchem-32 28 47 3 3 NUM eurjchem-32 28 48         SPACE eurjchem-32 28 49 2.3 2.3 NUM eurjchem-32 28 50 . . PUNCT eurjchem-32 28 51     SPACE eurjchem-32 29 1 5­amino­6­(benzo[d]thiazol­2­yl)­7­(4­chlorophenyl)­2­ 5­amino­6­(benzo[d]thiazol­2­yl)­7­(4­chlorophenyl)­2­ NOUN eurjchem-32 29 2 thioxo­2,3­dihydropyrido[2,3­d]pyrimidin­4(1h)­one thioxo­2,3­dihydropyrido[2,3­d]pyrimidin­4(1h)­one NOUN eurjchem-32 29 3 , , PUNCT eurjchem-32 29 4     SPACE eurjchem-32 29 5 8 8 NUM eurjchem-32 29 6           SPACE eurjchem-32 29 7 to to ADP eurjchem-32 29 8     SPACE eurjchem-32 29 9 a a DET eurjchem-32 29 10     SPACE eurjchem-32 29 11 mixture mixture NOUN eurjchem-32 29 12     SPACE eurjchem-32 29 13 of of ADP eurjchem-32 29 14     SPACE eurjchem-32 29 15 4 4 NUM eurjchem-32 29 16     SPACE eurjchem-32 29 17 ( ( PUNCT eurjchem-32 29 18 2.41 2.41 NUM eurjchem-32 29 19     SPACE eurjchem-32 29 20 g g NOUN eurjchem-32 29 21 , , PUNCT eurjchem-32 29 22     SPACE eurjchem-32 29 23 0.01 0.01 NUM eurjchem-32 29 24     SPACE eurjchem-32 29 25 mol mol NOUN eurjchem-32 29 26 ) ) PUNCT eurjchem-32 29 27 , , PUNCT eurjchem-32 29 28     SPACE eurjchem-32 29 29 p‐chlorobenzaldehyde p‐chlorobenzaldehyde NOUN eurjchem-32 29 30     SPACE eurjchem-32 29 31 ( ( PUNCT eurjchem-32 29 32 1.41 1.41 NUM eurjchem-32 29 33     SPACE eurjchem-32 29 34 g g NOUN eurjchem-32 29 35 , , PUNCT eurjchem-32 29 36     SPACE eurjchem-32 29 37 0.01 0.01 NUM eurjchem-32 29 38     SPACE eurjchem-32 29 39 mol mol NOUN eurjchem-32 29 40 ) ) PUNCT eurjchem-32 29 41     SPACE eurjchem-32 29 42 and and CCONJ eurjchem-32 29 43     SPACE eurjchem-32 29 44 6‐aminothiouracil 6‐aminothiouracil NUM eurjchem-32 29 45     SPACE eurjchem-32 29 46 ( ( PUNCT eurjchem-32 29 47 7 7 NUM eurjchem-32 29 48 ) ) PUNCT eurjchem-32 29 49     SPACE eurjchem-32 29 50 ( ( PUNCT eurjchem-32 29 51 1.43 1.43 NUM eurjchem-32 29 52     SPACE eurjchem-32 29 53 g g NOUN eurjchem-32 29 54 , , PUNCT eurjchem-32 29 55     SPACE eurjchem-32 29 56 0.01 0.01 NUM eurjchem-32 29 57     SPACE eurjchem-32 29 58 mol mol NOUN eurjchem-32 29 59 ) ) PUNCT eurjchem-32 29 60     SPACE eurjchem-32 29 61 in in ADP eurjchem-32 29 62     SPACE eurjchem-32 29 63 ethanol ethanol NOUN eurjchem-32 29 64     SPACE eurjchem-32 29 65 ( ( PUNCT eurjchem-32 29 66 15 15 NUM eurjchem-32 29 67     SPACE eurjchem-32 29 68 ml ml NOUN eurjchem-32 29 69 ) ) PUNCT eurjchem-32 29 70 , , PUNCT eurjchem-32 29 71     SPACE eurjchem-32 29 72 a a DET eurjchem-32 29 73     SPACE eurjchem-32 29 74 catalytic catalytic ADJ eurjchem-32 29 75     SPACE eurjchem-32 29 76 amount amount NOUN eurjchem-32 29 77     SPACE eurjchem-32 29 78 of of ADP eurjchem-32 29 79     SPACE eurjchem-32 29 80 piperidine piperidine NOUN eurjchem-32 29 81     SPACE eurjchem-32 29 82 was be AUX eurjchem-32 29 83     SPACE eurjchem-32 29 84 added add VERB eurjchem-32 29 85     SPACE eurjchem-32 29 86 ( ( PUNCT eurjchem-32 29 87 scheme scheme NOUN eurjchem-32 29 88     SPACE eurjchem-32 29 89 4 4 NUM eurjchem-32 29 90 ) ) PUNCT eurjchem-32 29 91 . . PUNCT eurjchem-32 29 92     SPACE eurjchem-32 30 1 the the DET eurjchem-32 30 2     SPACE eurjchem-32 30 3 reaction reaction NOUN eurjchem-32 30 4     SPACE eurjchem-32 30 5 mixture mixture NOUN eurjchem-32 30 6     SPACE eurjchem-32 30 7 was be AUX eurjchem-32 30 8     SPACE eurjchem-32 30 9 refluxed refluxe VERB eurjchem-32 30 10     SPACE eurjchem-32 30 11 for for ADP eurjchem-32 30 12     SPACE eurjchem-32 30 13 6 6 NUM eurjchem-32 30 14     SPACE eurjchem-32 30 15 h h NOUN eurjchem-32 30 16 , , PUNCT eurjchem-32 30 17     SPACE eurjchem-32 30 18 allowed allow VERB eurjchem-32 30 19     SPACE eurjchem-32 30 20 to to PART eurjchem-32 30 21     SPACE eurjchem-32 30 22 cool cool VERB eurjchem-32 30 23     SPACE eurjchem-32 30 24 and and CCONJ eurjchem-32 30 25     SPACE eurjchem-32 30 26 poured pour VERB eurjchem-32 30 27     SPACE eurjchem-32 30 28 into into ADP eurjchem-32 30 29     SPACE eurjchem-32 30 30 ice ice NOUN eurjchem-32 30 31     SPACE eurjchem-32 30 32 cold cold ADJ eurjchem-32 30 33     SPACE eurjchem-32 30 34 water water NOUN eurjchem-32 30 35 . . PUNCT eurjchem-32 30 36     SPACE eurjchem-32 31 1 the the DET eurjchem-32 31 2     SPACE eurjchem-32 31 3 precipitated precipitate VERB eurjchem-32 31 4     SPACE eurjchem-32 31 5 solid solid NOUN eurjchem-32 31 6     SPACE eurjchem-32 31 7 obtained obtain VERB eurjchem-32 31 8     SPACE eurjchem-32 31 9 was be AUX eurjchem-32 31 10     SPACE eurjchem-32 31 11 filtered filter VERB eurjchem-32 31 12     SPACE eurjchem-32 31 13 off off ADP eurjchem-32 31 14 , , PUNCT eurjchem-32 31 15     SPACE eurjchem-32 31 16 dried dry VERB eurjchem-32 31 17     SPACE eurjchem-32 31 18 and and CCONJ eurjchem-32 31 19     SPACE eurjchem-32 31 20 recrystallized recrystallize VERB eurjchem-32 31 21     SPACE eurjchem-32 31 22 from from ADP eurjchem-32 31 23     SPACE eurjchem-32 31 24 ethanol ethanol NOUN eurjchem-32 31 25     SPACE eurjchem-32 31 26 to to PART eurjchem-32 31 27     SPACE eurjchem-32 31 28 furnish furnish VERB eurjchem-32 31 29     SPACE eurjchem-32 31 30 2.72 2.72 NUM eurjchem-32 31 31     SPACE eurjchem-32 31 32 g g NOUN eurjchem-32 31 33     SPACE eurjchem-32 31 34 ( ( PUNCT eurjchem-32 31 35 62 62 NUM eurjchem-32 31 36 % % NOUN eurjchem-32 31 37 ) ) PUNCT eurjchem-32 31 38     SPACE eurjchem-32 31 39 of of ADP eurjchem-32 31 40     SPACE eurjchem-32 31 41 8 8 NUM eurjchem-32 31 42 ; ; PUNCT eurjchem-32 31 43     SPACE eurjchem-32 31 44 mp mp NOUN eurjchem-32 31 45     SPACE eurjchem-32 31 46 230 230 NUM eurjchem-32 31 47     SPACE eurjchem-32 31 48 oc oc NOUN eurjchem-32 31 49 ; ; PUNCT eurjchem-32 31 50     SPACE eurjchem-32 31 51 pale pale ADJ eurjchem-32 31 52     SPACE eurjchem-32 31 53 yellow yellow ADJ eurjchem-32 31 54     SPACE eurjchem-32 31 55 powder powder NOUN eurjchem-32 31 56 ; ; PUNCT eurjchem-32 31 57     SPACE eurjchem-32 31 58 ir ir VERB eurjchem-32 31 59     SPACE eurjchem-32 31 60 ( ( PUNCT eurjchem-32 31 61 kbr kbr PROPN eurjchem-32 31 62 ) ) PUNCT eurjchem-32 31 63     SPACE eurjchem-32 31 64 ( ( PUNCT eurjchem-32 31 65 υ υ NOUN eurjchem-32 31 66 , , PUNCT eurjchem-32 31 67     SPACE eurjchem-32 31 68 cm‐1 cm‐1 NOUN eurjchem-32 31 69 ): ): PUNCT eurjchem-32 31 70     SPACE eurjchem-32 31 71 3402 3402 NUM eurjchem-32 31 72 , , PUNCT eurjchem-32 31 73     SPACE eurjchem-32 31 74 3389 3389 NUM eurjchem-32 31 75     SPACE eurjchem-32 31 76 ( ( PUNCT eurjchem-32 31 77 nh2 nh2 PROPN eurjchem-32 31 78 ) ) PUNCT eurjchem-32 31 79 , , PUNCT eurjchem-32 31 80     SPACE eurjchem-32 31 81 3141 3141 NUM eurjchem-32 31 82     SPACE eurjchem-32 31 83 ( ( PUNCT eurjchem-32 31 84 nh nh NOUN eurjchem-32 31 85 ) ) PUNCT eurjchem-32 31 86 , , PUNCT eurjchem-32 31 87     SPACE eurjchem-32 31 88 1698 1698 NUM eurjchem-32 31 89     SPACE eurjchem-32 31 90 ( ( PUNCT eurjchem-32 31 91 co co NOUN eurjchem-32 31 92 ) ) PUNCT eurjchem-32 31 93 , , PUNCT eurjchem-32 31 94     SPACE eurjchem-32 31 95 1221 1221 NUM eurjchem-32 31 96     SPACE eurjchem-32 31 97 ( ( PUNCT eurjchem-32 31 98 c c PROPN eurjchem-32 31 99 = = SYM eurjchem-32 31 100 s s NOUN eurjchem-32 31 101 ) ) PUNCT eurjchem-32 31 102 . . PUNCT eurjchem-32 31 103     SPACE eurjchem-32 31 104 1h 1h NUM eurjchem-32 31 105     SPACE eurjchem-32 31 106 nmr nmr NOUN eurjchem-32 31 107     SPACE eurjchem-32 31 108 ( ( PUNCT eurjchem-32 31 109 dmso‐d6 dmso‐d6 NOUN eurjchem-32 31 110 ): ): PUNCT eurjchem-32 31 111     SPACE eurjchem-32 31 112 δ δ PROPN eurjchem-32 31 113 , , PUNCT eurjchem-32 31 114     SPACE eurjchem-32 31 115 6.22 6.22 NUM eurjchem-32 31 116     SPACE eurjchem-32 31 117 ( ( PUNCT eurjchem-32 31 118 s s PROPN eurjchem-32 31 119 , , PUNCT eurjchem-32 31 120     SPACE eurjchem-32 31 121 2h 2h NUM eurjchem-32 31 122 , , PUNCT eurjchem-32 31 123     SPACE eurjchem-32 31 124 nh2 nh2 PROPN eurjchem-32 31 125 ) ) PUNCT eurjchem-32 31 126 , , PUNCT eurjchem-32 31 127     SPACE eurjchem-32 31 128 7.32‐8.49 7.32‐8.49 NUM eurjchem-32 31 129     SPACE eurjchem-32 31 130 ( ( PUNCT eurjchem-32 31 131 m m PROPN eurjchem-32 31 132 , , PUNCT eurjchem-32 31 133     SPACE eurjchem-32 31 134 8h 8h NUM eurjchem-32 31 135 , , PUNCT eurjchem-32 31 136     SPACE eurjchem-32 31 137 ar‐h ar‐h NOUN eurjchem-32 31 138 ) ) PUNCT eurjchem-32 31 139 , , PUNCT eurjchem-32 31 140     SPACE eurjchem-32 31 141 13.51 13.51 NUM eurjchem-32 31 142     SPACE eurjchem-32 31 143 ( ( PUNCT eurjchem-32 31 144 s s PROPN eurjchem-32 31 145 , , PUNCT eurjchem-32 31 146     SPACE eurjchem-32 31 147 1h 1h NUM eurjchem-32 31 148 , , PUNCT eurjchem-32 31 149     SPACE eurjchem-32 31 150 nh nh PROPN eurjchem-32 31 151 ) ) PUNCT eurjchem-32 31 152 , , PUNCT eurjchem-32 31 153     SPACE eurjchem-32 31 154 13.59 13.59 NUM eurjchem-32 31 155     SPACE eurjchem-32 31 156 ( ( PUNCT eurjchem-32 31 157 s s PROPN eurjchem-32 31 158 , , PUNCT eurjchem-32 31 159     SPACE eurjchem-32 31 160 1h 1h NUM eurjchem-32 31 161 , , PUNCT eurjchem-32 31 162     SPACE eurjchem-32 31 163 nh nh PROPN eurjchem-32 31 164 ) ) PUNCT eurjchem-32 31 165 . . PUNCT eurjchem-32 31 166     SPACE eurjchem-32 32 1 ms ms NOUN eurjchem-32 32 2 : : PUNCT eurjchem-32 32 3     SPACE eurjchem-32 32 4 ( ( PUNCT eurjchem-32 32 5 m m PROPN eurjchem-32 32 6 / / SYM eurjchem-32 32 7 z z NOUN eurjchem-32 32 8 , , PUNCT eurjchem-32 32 9     SPACE eurjchem-32 32 10 % % NOUN eurjchem-32 32 11 ): ): PUNCT eurjchem-32 32 12     SPACE eurjchem-32 32 13 438 438 NUM eurjchem-32 32 14     SPACE eurjchem-32 32 15 ( ( PUNCT eurjchem-32 32 16 m+ m+ NUM eurjchem-32 32 17 , , PUNCT eurjchem-32 32 18     SPACE eurjchem-32 32 19 36.4 36.4 NUM eurjchem-32 32 20 ) ) PUNCT eurjchem-32 32 21 , , PUNCT eurjchem-32 32 22     SPACE eurjchem-32 32 23 203 203 NUM eurjchem-32 32 24     SPACE eurjchem-32 32 25 ( ( PUNCT eurjchem-32 32 26 18.2 18.2 NUM eurjchem-32 32 27 ) ) PUNCT eurjchem-32 32 28 , , PUNCT eurjchem-32 32 29     SPACE eurjchem-32 32 30 143 143 NUM eurjchem-32 32 31     SPACE eurjchem-32 32 32 ( ( PUNCT eurjchem-32 32 33 75.8 75.8 NUM eurjchem-32 32 34 ) ) PUNCT eurjchem-32 32 35 , , PUNCT eurjchem-32 32 36     SPACE eurjchem-32 32 37 111 111 NUM eurjchem-32 32 38     SPACE eurjchem-32 32 39 ( ( PUNCT eurjchem-32 32 40 57.6 57.6 NUM eurjchem-32 32 41 ) ) PUNCT eurjchem-32 32 42 , , PUNCT eurjchem-32 32 43     SPACE eurjchem-32 32 44 63 63 NUM eurjchem-32 32 45     SPACE eurjchem-32 32 46 ( ( PUNCT eurjchem-32 32 47 100.0 100.0 NUM eurjchem-32 32 48 ) ) PUNCT eurjchem-32 32 49 . . PUNCT eurjchem-32 32 50     SPACE eurjchem-32 33 1 anal anal ADJ eurjchem-32 33 2 . . PUNCT eurjchem-32 33 3     SPACE eurjchem-32 33 4 calcd calcd NOUN eurjchem-32 33 5 . . PUNCT eurjchem-32 33 6     SPACE eurjchem-32 33 7 for for ADP eurjchem-32 33 8     SPACE eurjchem-32 33 9 c20h12cln5os2 c20h12cln5os2 NOUN eurjchem-32 33 10 : : PUNCT eurjchem-32 33 11     SPACE eurjchem-32 33 12 c c X eurjchem-32 33 13 , , PUNCT eurjchem-32 33 14     SPACE eurjchem-32 33 15 54.84 54.84 NUM eurjchem-32 33 16 ; ; PUNCT eurjchem-32 33 17     SPACE eurjchem-32 33 18 h h NOUN eurjchem-32 33 19 , , PUNCT eurjchem-32 33 20     SPACE eurjchem-32 33 21 2.76 2.76 NUM eurjchem-32 33 22 ; ; PUNCT eurjchem-32 33 23     SPACE eurjchem-32 33 24 n n CCONJ eurjchem-32 33 25 , , PUNCT eurjchem-32 33 26     SPACE eurjchem-32 33 27 15.99 15.99 NUM eurjchem-32 33 28 . . PUNCT eurjchem-32 33 29     SPACE eurjchem-32 33 30 found find VERB eurjchem-32 33 31 : : PUNCT eurjchem-32 33 32     SPACE eurjchem-32 33 33 c c X eurjchem-32 33 34 , , PUNCT eurjchem-32 33 35     SPACE eurjchem-32 33 36 54.94 54.94 NUM eurjchem-32 33 37 ; ; PUNCT eurjchem-32 33 38     SPACE eurjchem-32 33 39 h h NOUN eurjchem-32 33 40 , , PUNCT eurjchem-32 33 41     SPACE eurjchem-32 33 42 2.82 2.82 NUM eurjchem-32 33 43 ; ; PUNCT eurjchem-32 33 44     SPACE eurjchem-32 33 45 n n CCONJ eurjchem-32 33 46 , , PUNCT eurjchem-32 33 47     SPACE eurjchem-32 33 48 16.04 16.04 NUM eurjchem-32 33 49 . . PUNCT eurjchem-32 33 50     SPACE eurjchem-32 33 51 scheme scheme NOUN eurjchem-32 33 52     SPACE eurjchem-32 33 53 4 4 NUM eurjchem-32 33 54         SPACE eurjchem-32 33 55 2.4 2.4 NUM eurjchem-32 33 56 . . PUNCT eurjchem-32 33 57     SPACE eurjchem-32 33 58 5­amino­6­(benzo[d]thiazol­2­yl)­7­(1,4­diphenyl­1h­ 5­amino­6­(benzo[d]thiazol­2­yl)­7­(1,4­diphenyl­1h­ NUM eurjchem-32 33 59 pyrazol­3­yl)­1­methylpyrido[2,3­d]pyrimidine­2,4(1h,3h)­ pyrazol­3­yl)­1­methylpyrido[2,3­d]pyrimidine­2,4(1h,3h)­ PROPN eurjchem-32 33 60 dione dione NOUN eurjchem-32 33 61 , , PUNCT eurjchem-32 33 62     SPACE eurjchem-32 33 63 11 11 NUM eurjchem-32 33 64           SPACE eurjchem-32 33 65 to to ADP eurjchem-32 33 66     SPACE eurjchem-32 33 67 a a DET eurjchem-32 33 68     SPACE eurjchem-32 33 69 mixture mixture NOUN eurjchem-32 33 70     SPACE eurjchem-32 33 71 of of ADP eurjchem-32 33 72     SPACE eurjchem-32 33 73 4 4 NUM eurjchem-32 33 74     SPACE eurjchem-32 33 75 ( ( PUNCT eurjchem-32 33 76 2.41 2.41 NUM eurjchem-32 33 77     SPACE eurjchem-32 33 78 g g NOUN eurjchem-32 33 79 , , PUNCT eurjchem-32 33 80     SPACE eurjchem-32 33 81 0.01 0.01 NUM eurjchem-32 33 82     SPACE eurjchem-32 33 83 mol mol NOUN eurjchem-32 33 84 ) ) PUNCT eurjchem-32 33 85 , , PUNCT eurjchem-32 33 86     SPACE eurjchem-32 33 87 6‐amino‐1‐ 6‐amino‐1‐ PROPN eurjchem-32 33 88 methylpyrimidine‐2,4(1h,3h)‐dione methylpyrimidine‐2,4(1h,3h)‐dione VERB eurjchem-32 33 89     SPACE eurjchem-32 33 90 ( ( PUNCT eurjchem-32 33 91 9 9 NUM eurjchem-32 33 92 ) ) PUNCT eurjchem-32 33 93     SPACE eurjchem-32 33 94 ( ( PUNCT eurjchem-32 33 95 1.41 1.41 NUM eurjchem-32 33 96     SPACE eurjchem-32 33 97 g g NOUN eurjchem-32 33 98 , , PUNCT eurjchem-32 33 99     SPACE eurjchem-32 33 100 0.01 0.01 NUM eurjchem-32 33 101     SPACE eurjchem-32 33 102 mol mol NOUN eurjchem-32 33 103 ) ) PUNCT eurjchem-32 33 104     SPACE eurjchem-32 33 105 and and CCONJ eurjchem-32 33 106     SPACE eurjchem-32 33 107 1,4‐diphenyl‐1h‐pyrazole‐3‐carbaldehyde 1,4‐diphenyl‐1h‐pyrazole‐3‐carbaldehyde NOUN eurjchem-32 33 108     SPACE eurjchem-32 33 109 ( ( PUNCT eurjchem-32 33 110 10 10 NUM eurjchem-32 33 111 ) ) PUNCT eurjchem-32 33 112     SPACE eurjchem-32 33 113 ( ( PUNCT eurjchem-32 33 114 2.48 2.48 NUM eurjchem-32 33 115     SPACE eurjchem-32 33 116 g g NOUN eurjchem-32 33 117 , , PUNCT eurjchem-32 33 118     SPACE eurjchem-32 33 119 0.01 0.01 NUM eurjchem-32 33 120     SPACE eurjchem-32 33 121 mol mol NOUN eurjchem-32 33 122 ) ) PUNCT eurjchem-32 33 123     SPACE eurjchem-32 33 124 in in ADP eurjchem-32 33 125     SPACE eurjchem-32 33 126 dmf dmf PROPN eurjchem-32 33 127     SPACE eurjchem-32 33 128 ( ( PUNCT eurjchem-32 33 129 15 15 NUM eurjchem-32 33 130     SPACE eurjchem-32 33 131 ml ml NOUN eurjchem-32 33 132 ) ) PUNCT eurjchem-32 33 133 , , PUNCT eurjchem-32 33 134     SPACE eurjchem-32 33 135 a a DET eurjchem-32 33 136     SPACE eurjchem-32 33 137 catalytic catalytic ADJ eurjchem-32 33 138     SPACE eurjchem-32 33 139 amount amount NOUN eurjchem-32 33 140     SPACE eurjchem-32 33 141 of of ADP eurjchem-32 33 142     SPACE eurjchem-32 33 143 tea tea NOUN eurjchem-32 33 144     SPACE eurjchem-32 33 145 was be AUX eurjchem-32 33 146     SPACE eurjchem-32 33 147 added add VERB eurjchem-32 33 148     SPACE eurjchem-32 33 149 ( ( PUNCT eurjchem-32 33 150 scheme scheme NOUN eurjchem-32 33 151     SPACE eurjchem-32 33 152 5 5 NUM eurjchem-32 33 153 ) ) PUNCT eurjchem-32 33 154 . . PUNCT eurjchem-32 33 155     SPACE eurjchem-32 34 1 the the DET eurjchem-32 34 2     SPACE eurjchem-32 34 3 reaction reaction NOUN eurjchem-32 34 4     SPACE eurjchem-32 34 5 mixture mixture NOUN eurjchem-32 34 6     SPACE eurjchem-32 34 7 was be AUX eurjchem-32 34 8     SPACE eurjchem-32 34 9 refluxed refluxe VERB eurjchem-32 34 10     SPACE eurjchem-32 34 11 for for ADP eurjchem-32 34 12     SPACE eurjchem-32 34 13 6 6 NUM eurjchem-32 34 14     SPACE eurjchem-32 34 15 h h NOUN eurjchem-32 34 16 , , PUNCT eurjchem-32 34 17     SPACE eurjchem-32 34 18 allowed allow VERB eurjchem-32 34 19     SPACE eurjchem-32 34 20 to to PART eurjchem-32 34 21     SPACE eurjchem-32 34 22 cool cool VERB eurjchem-32 34 23     SPACE eurjchem-32 34 24 and and CCONJ eurjchem-32 34 25     SPACE eurjchem-32 34 26 poured pour VERB eurjchem-32 34 27     SPACE eurjchem-32 34 28 into into ADP eurjchem-32 34 29     SPACE eurjchem-32 34 30 ice ice NOUN eurjchem-32 34 31     SPACE eurjchem-32 34 32 cold cold ADJ eurjchem-32 34 33     SPACE eurjchem-32 34 34 water water NOUN eurjchem-32 34 35 . . PUNCT eurjchem-32 34 36     SPACE eurjchem-32 35 1 the the DET eurjchem-32 35 2     SPACE eurjchem-32 35 3 precipitated precipitate VERB eurjchem-32 35 4     SPACE eurjchem-32 35 5 solid solid NOUN eurjchem-32 35 6     SPACE eurjchem-32 35 7 obtained obtain VERB eurjchem-32 35 8     SPACE eurjchem-32 35 9 was be AUX eurjchem-32 35 10     SPACE eurjchem-32 35 11 filtered filter VERB eurjchem-32 35 12     SPACE eurjchem-32 35 13 off off ADP eurjchem-32 35 14 , , PUNCT eurjchem-32 35 15     SPACE eurjchem-32 35 16 dried dry VERB eurjchem-32 35 17     SPACE eurjchem-32 35 18 and and CCONJ eurjchem-32 35 19     SPACE eurjchem-32 35 20 recrystallized recrystallize VERB eurjchem-32 35 21     SPACE eurjchem-32 35 22 from from ADP eurjchem-32 35 23     SPACE eurjchem-32 35 24 ethanol ethanol NOUN eurjchem-32 35 25     SPACE eurjchem-32 35 26 to to PART eurjchem-32 35 27     SPACE eurjchem-32 35 28 furnish furnish VERB eurjchem-32 35 29     SPACE eurjchem-32 35 30 2.94 2.94 NUM eurjchem-32 35 31     SPACE eurjchem-32 35 32 g g NOUN eurjchem-32 35 33     SPACE eurjchem-32 35 34 ( ( PUNCT eurjchem-32 35 35 54 54 NUM eurjchem-32 35 36 % % NOUN eurjchem-32 35 37 ) ) PUNCT eurjchem-32 35 38     SPACE eurjchem-32 35 39 of of ADP eurjchem-32 35 40     SPACE eurjchem-32 35 41 11 11 NUM eurjchem-32 35 42 ; ; PUNCT eurjchem-32 35 43     SPACE eurjchem-32 35 44 mp mp NOUN eurjchem-32 35 45     SPACE eurjchem-32 35 46 165 165 NUM eurjchem-32 35 47     SPACE eurjchem-32 35 48 oc oc NOUN eurjchem-32 35 49 ; ; PUNCT eurjchem-32 35 50     SPACE eurjchem-32 35 51 pale pale ADJ eurjchem-32 35 52     SPACE eurjchem-32 35 53 brown brown ADJ eurjchem-32 35 54     SPACE eurjchem-32 35 55 powder powder NOUN eurjchem-32 35 56 ; ; PUNCT eurjchem-32 35 57     SPACE eurjchem-32 35 58 ir ir PROPN eurjchem-32 35 59     SPACE eurjchem-32 35 60 ( ( PUNCT eurjchem-32 35 61 kbr kbr PROPN eurjchem-32 35 62 ) ) PUNCT eurjchem-32 35 63     SPACE eurjchem-32 35 64 ( ( PUNCT eurjchem-32 35 65 υ υ NOUN eurjchem-32 35 66 , , PUNCT eurjchem-32 35 67     SPACE eurjchem-32 35 68 cm‐1 cm‐1 NOUN eurjchem-32 35 69 ): ): PUNCT eurjchem-32 35 70     SPACE eurjchem-32 35 71 3400 3400 NUM eurjchem-32 35 72 , , PUNCT eurjchem-32 35 73     SPACE eurjchem-32 35 74 3365 3365 NUM eurjchem-32 35 75     SPACE eurjchem-32 35 76 ( ( PUNCT eurjchem-32 35 77 nh2 nh2 PROPN eurjchem-32 35 78 ) ) PUNCT eurjchem-32 35 79 , , PUNCT eurjchem-32 35 80     SPACE eurjchem-32 35 81 3220 3220 NUM eurjchem-32 35 82     SPACE eurjchem-32 35 83 ( ( PUNCT eurjchem-32 35 84 nh nh NOUN eurjchem-32 35 85 ) ) PUNCT eurjchem-32 35 86 , , PUNCT eurjchem-32 35 87     SPACE eurjchem-32 35 88 1695 1695 NUM eurjchem-32 35 89     SPACE eurjchem-32 35 90 ( ( PUNCT eurjchem-32 35 91 amidic amidic NOUN eurjchem-32 35 92     SPACE eurjchem-32 35 93 co co NOUN eurjchem-32 35 94 ) ) PUNCT eurjchem-32 35 95 . . PUNCT eurjchem-32 35 96     SPACE eurjchem-32 35 97 1h 1h NUM eurjchem-32 35 98     SPACE eurjchem-32 35 99 nmr nmr NOUN eurjchem-32 35 100     SPACE eurjchem-32 35 101 ( ( PUNCT eurjchem-32 35 102 dmso‐d6 dmso‐d6 NOUN eurjchem-32 35 103 ): ): PUNCT eurjchem-32 35 104     SPACE eurjchem-32 35 105 δ δ PROPN eurjchem-32 35 106 , , PUNCT eurjchem-32 35 107     SPACE eurjchem-32 35 108 3.4 3.4 NUM eurjchem-32 35 109     SPACE eurjchem-32 35 110 ( ( PUNCT eurjchem-32 35 111 s s PROPN eurjchem-32 35 112 , , PUNCT eurjchem-32 35 113     SPACE eurjchem-32 35 114 3h 3h NUM eurjchem-32 35 115 , , PUNCT eurjchem-32 35 116     SPACE eurjchem-32 35 117 ch3 ch3 PROPN eurjchem-32 35 118 ) ) PUNCT eurjchem-32 35 119 , , PUNCT eurjchem-32 35 120     SPACE eurjchem-32 35 121 6.27 6.27 NUM eurjchem-32 35 122     SPACE eurjchem-32 35 123 ( ( PUNCT eurjchem-32 35 124 s s PROPN eurjchem-32 35 125 , , PUNCT eurjchem-32 35 126     SPACE eurjchem-32 35 127 2h 2h NUM eurjchem-32 35 128 , , PUNCT eurjchem-32 35 129     SPACE eurjchem-32 35 130 nh2 nh2 PROPN eurjchem-32 35 131 ) ) PUNCT eurjchem-32 35 132 , , PUNCT eurjchem-32 35 133     SPACE eurjchem-32 35 134 7.51‐8.18 7.51‐8.18 NUM eurjchem-32 35 135     SPACE eurjchem-32 35 136 ( ( PUNCT eurjchem-32 35 137 m m PROPN eurjchem-32 35 138 , , PUNCT eurjchem-32 35 139     SPACE eurjchem-32 35 140 4h 4h NOUN eurjchem-32 35 141 , , PUNCT eurjchem-32 35 142     SPACE eurjchem-32 35 143 ar‐h ar‐h NOUN eurjchem-32 35 144 ) ) PUNCT eurjchem-32 35 145 , , PUNCT eurjchem-32 35 146     SPACE eurjchem-32 35 147 9.3 9.3 NUM eurjchem-32 35 148     SPACE eurjchem-32 35 149 ( ( PUNCT eurjchem-32 35 150 s s PROPN eurjchem-32 35 151 , , PUNCT eurjchem-32 35 152     SPACE eurjchem-32 35 153 1h 1h NUM eurjchem-32 35 154 , , PUNCT eurjchem-32 35 155     SPACE eurjchem-32 35 156 ch ch NOUN eurjchem-32 35 157 ) ) PUNCT eurjchem-32 35 158 , , PUNCT eurjchem-32 35 159     SPACE eurjchem-32 35 160 10.1 10.1 NUM eurjchem-32 35 161     SPACE eurjchem-32 35 162 ( ( PUNCT eurjchem-32 35 163 s s PROPN eurjchem-32 35 164 , , PUNCT eurjchem-32 35 165     SPACE eurjchem-32 35 166 1h 1h NUM eurjchem-32 35 167 , , PUNCT eurjchem-32 35 168     SPACE eurjchem-32 35 169 nh nh PROPN eurjchem-32 35 170 ) ) PUNCT eurjchem-32 35 171 . . PUNCT eurjchem-32 35 172     SPACE eurjchem-32 36 1 ms ms NOUN eurjchem-32 36 2 : : PUNCT eurjchem-32 36 3     SPACE eurjchem-32 36 4 ( ( PUNCT eurjchem-32 36 5 m m PROPN eurjchem-32 36 6 / / SYM eurjchem-32 36 7 z z NOUN eurjchem-32 36 8 , , PUNCT eurjchem-32 36 9     SPACE eurjchem-32 36 10 % % NOUN eurjchem-32 36 11 ): ): PUNCT eurjchem-32 36 12     SPACE eurjchem-32 36 13 543 543 NUM eurjchem-32 36 14     SPACE eurjchem-32 36 15 ( ( PUNCT eurjchem-32 36 16 m+ m+ NUM eurjchem-32 36 17 , , PUNCT eurjchem-32 36 18     SPACE eurjchem-32 36 19 10 10 NUM eurjchem-32 36 20 ) ) PUNCT eurjchem-32 36 21 . . PUNCT eurjchem-32 36 22     SPACE eurjchem-32 37 1 anal anal ADJ eurjchem-32 37 2 . . PUNCT eurjchem-32 37 3     SPACE eurjchem-32 37 4 calcd calcd NOUN eurjchem-32 37 5 . . PUNCT eurjchem-32 37 6     SPACE eurjchem-32 37 7 for for ADP eurjchem-32 37 8     SPACE eurjchem-32 37 9 c30h21n7o2s c30h21n7o2s NUM eurjchem-32 37 10 : : PUNCT eurjchem-32 37 11     SPACE eurjchem-32 37 12 c c X eurjchem-32 37 13 , , PUNCT eurjchem-32 37 14     SPACE eurjchem-32 37 15 66.28 66.28 NUM eurjchem-32 37 16 ; ; PUNCT eurjchem-32 37 17     SPACE eurjchem-32 37 18 h h NOUN eurjchem-32 37 19 , , PUNCT eurjchem-32 37 20     SPACE eurjchem-32 37 21 3.89 3.89 NUM eurjchem-32 37 22 ; ; PUNCT eurjchem-32 37 23     SPACE eurjchem-32 37 24 n n CCONJ eurjchem-32 37 25 , , PUNCT eurjchem-32 37 26     SPACE eurjchem-32 37 27 18.04 18.04 NUM eurjchem-32 37 28 . . PUNCT eurjchem-32 37 29     SPACE eurjchem-32 37 30 found find VERB eurjchem-32 37 31 : : PUNCT eurjchem-32 37 32     SPACE eurjchem-32 37 33 c c X eurjchem-32 37 34 , , PUNCT eurjchem-32 37 35     SPACE eurjchem-32 37 36 66.26 66.26 NUM eurjchem-32 37 37 ; ; PUNCT eurjchem-32 37 38     SPACE eurjchem-32 37 39 h h NOUN eurjchem-32 37 40 , , PUNCT eurjchem-32 37 41     SPACE eurjchem-32 37 42 3.83 3.83 NUM eurjchem-32 37 43 ; ; PUNCT eurjchem-32 37 44     SPACE eurjchem-32 37 45 n n CCONJ eurjchem-32 37 46 , , PUNCT eurjchem-32 37 47     SPACE eurjchem-32 37 48 18.01 18.01 NUM eurjchem-32 37 49 . . PUNCT eurjchem-32 37 50         SPACE eurjchem-32 37 51 scheme scheme NOUN eurjchem-32 37 52     SPACE eurjchem-32 37 53 5 5 NUM eurjchem-32 37 54         SPACE eurjchem-32 37 55 2.5 2.5 NUM eurjchem-32 37 56 . . PUNCT eurjchem-32 37 57     SPACE eurjchem-32 38 1 5­amino­7­(benzo[d][1,3]dioxol­5­yl)­6­(benzo[d 5­amino­7­(benzo[d][1,3]dioxol­5­yl)­6­(benzo[d NOUN eurjchem-32 38 2 ] ] PUNCT eurjchem-32 38 3     SPACE eurjchem-32 38 4 thiazol­2­yl)­1,3­dimethylpyrido[2,3­d]pyrimidine­ thiazol­2­yl)­1,3­dimethylpyrido[2,3­d]pyrimidine­ NOUN eurjchem-32 38 5 2,4(1h,3h)­dione 2,4(1h,3h)­dione NUM eurjchem-32 38 6 , , PUNCT eurjchem-32 38 7     SPACE eurjchem-32 38 8 14 14 NUM eurjchem-32 38 9           SPACE eurjchem-32 38 10 to to ADP eurjchem-32 38 11     SPACE eurjchem-32 38 12 a a DET eurjchem-32 38 13     SPACE eurjchem-32 38 14 mixture mixture NOUN eurjchem-32 38 15     SPACE eurjchem-32 38 16 of of ADP eurjchem-32 38 17     SPACE eurjchem-32 38 18 4 4 NUM eurjchem-32 38 19     SPACE eurjchem-32 38 20 ( ( PUNCT eurjchem-32 38 21 2.41 2.41 NUM eurjchem-32 38 22     SPACE eurjchem-32 38 23 g g NOUN eurjchem-32 38 24 , , PUNCT eurjchem-32 38 25     SPACE eurjchem-32 38 26 0.01 0.01 NUM eurjchem-32 38 27     SPACE eurjchem-32 38 28 mol mol NOUN eurjchem-32 38 29 ) ) PUNCT eurjchem-32 38 30 , , PUNCT eurjchem-32 38 31     SPACE eurjchem-32 39 1 benzo[d][1,3 benzo[d][1,3 PROPN eurjchem-32 39 2 ] ] VERB eurjchem-32 39 3     SPACE eurjchem-32 39 4 dioxole‐ dioxole‐ NOUN eurjchem-32 39 5 5‐carbaldehyde 5‐carbaldehyde NOUN eurjchem-32 39 6     SPACE eurjchem-32 39 7 ( ( PUNCT eurjchem-32 39 8 12 12 NUM eurjchem-32 39 9 ) ) PUNCT eurjchem-32 39 10     SPACE eurjchem-32 39 11 ( ( PUNCT eurjchem-32 39 12 1.50 1.50 NUM eurjchem-32 39 13     SPACE eurjchem-32 39 14 g g NOUN eurjchem-32 39 15 , , PUNCT eurjchem-32 39 16     SPACE eurjchem-32 39 17 0.01 0.01 NUM eurjchem-32 39 18     SPACE eurjchem-32 39 19 mol mol NOUN eurjchem-32 39 20 ) ) PUNCT eurjchem-32 39 21     SPACE eurjchem-32 39 22 and and CCONJ eurjchem-32 39 23     SPACE eurjchem-32 39 24 6‐amino‐1,3‐ 6‐amino‐1,3‐ NUM eurjchem-32 39 25 dimethylpyrimidine‐2,4(1h,3h)‐dione dimethylpyrimidine‐2,4(1h,3h)‐dione NOUN eurjchem-32 39 26     SPACE eurjchem-32 39 27 ( ( PUNCT eurjchem-32 39 28 13 13 NUM eurjchem-32 39 29 ) ) PUNCT eurjchem-32 39 30     SPACE eurjchem-32 39 31 ( ( PUNCT eurjchem-32 39 32 1.55 1.55 NUM eurjchem-32 39 33     SPACE eurjchem-32 39 34 g g NOUN eurjchem-32 39 35 , , PUNCT eurjchem-32 39 36     SPACE eurjchem-32 39 37 0.01 0.01 NUM eurjchem-32 39 38     SPACE eurjchem-32 39 39 mol mol NOUN eurjchem-32 39 40 ) ) PUNCT eurjchem-32 39 41     SPACE eurjchem-32 39 42 in in ADP eurjchem-32 39 43     SPACE eurjchem-32 39 44 dmf dmf PROPN eurjchem-32 39 45     SPACE eurjchem-32 39 46 ( ( PUNCT eurjchem-32 39 47 15 15 NUM eurjchem-32 39 48     SPACE eurjchem-32 39 49 ml ml NOUN eurjchem-32 39 50 ) ) PUNCT eurjchem-32 39 51 , , PUNCT eurjchem-32 39 52     SPACE eurjchem-32 39 53 a a DET eurjchem-32 39 54     SPACE eurjchem-32 39 55 catalytic catalytic ADJ eurjchem-32 39 56     SPACE eurjchem-32 39 57 amount amount NOUN eurjchem-32 39 58     SPACE eurjchem-32 39 59 of of ADP eurjchem-32 39 60     SPACE eurjchem-32 39 61 tea tea NOUN eurjchem-32 39 62     SPACE eurjchem-32 39 63 was be AUX eurjchem-32 39 64     SPACE eurjchem-32 39 65 added add VERB eurjchem-32 39 66     SPACE eurjchem-32 39 67 ( ( PUNCT eurjchem-32 39 68 scheme scheme NOUN eurjchem-32 39 69     SPACE eurjchem-32 39 70 6 6 NUM eurjchem-32 39 71 ) ) PUNCT eurjchem-32 39 72 . . PUNCT eurjchem-32 39 73     SPACE eurjchem-32 40 1 the the DET eurjchem-32 40 2     SPACE eurjchem-32 40 3 reaction reaction NOUN eurjchem-32 40 4     SPACE eurjchem-32 40 5 mixture mixture NOUN eurjchem-32 40 6     SPACE eurjchem-32 40 7 was be AUX eurjchem-32 40 8     SPACE eurjchem-32 40 9 refluxed refluxe VERB eurjchem-32 40 10     SPACE eurjchem-32 40 11 for for ADP eurjchem-32 40 12     SPACE eurjchem-32 40 13 6 6 NUM eurjchem-32 40 14     SPACE eurjchem-32 40 15 h h NOUN eurjchem-32 40 16 , , PUNCT eurjchem-32 40 17     SPACE eurjchem-32 40 18 allowed allow VERB eurjchem-32 40 19     SPACE eurjchem-32 40 20 to to PART eurjchem-32 40 21     SPACE eurjchem-32 40 22 cool cool VERB eurjchem-32 40 23     SPACE eurjchem-32 40 24 and and CCONJ eurjchem-32 40 25     SPACE eurjchem-32 40 26 poured pour VERB eurjchem-32 40 27     SPACE eurjchem-32 40 28 into into ADP eurjchem-32 40 29     SPACE eurjchem-32 40 30 ice ice NOUN eurjchem-32 40 31     SPACE eurjchem-32 40 32 cold cold ADJ eurjchem-32 40 33     SPACE eurjchem-32 40 34 water water NOUN eurjchem-32 40 35 . . PUNCT eurjchem-32 40 36     SPACE eurjchem-32 41 1 the the DET eurjchem-32 41 2     SPACE eurjchem-32 41 3 precipitated precipitate VERB eurjchem-32 41 4     SPACE eurjchem-32 41 5 solid solid NOUN eurjchem-32 41 6     SPACE eurjchem-32 41 7 obtained obtain VERB eurjchem-32 41 8     SPACE eurjchem-32 41 9 was be AUX eurjchem-32 41 10     SPACE eurjchem-32 41 11 filtered filter VERB eurjchem-32 41 12     SPACE eurjchem-32 41 13 off off ADP eurjchem-32 41 14 , , PUNCT eurjchem-32 41 15     SPACE eurjchem-32 41 16 dried dry VERB eurjchem-32 41 17     SPACE eurjchem-32 41 18 and and CCONJ eurjchem-32 41 19     SPACE eurjchem-32 41 20 recrystallized recrystallize VERB eurjchem-32 41 21     SPACE eurjchem-32 41 22 from from ADP eurjchem-32 41 23     SPACE eurjchem-32 41 24 ethanol ethanol NOUN eurjchem-32 41 25     SPACE eurjchem-32 41 26 to to PART eurjchem-32 41 27     SPACE eurjchem-32 41 28 furnish furnish VERB eurjchem-32 41 29     SPACE eurjchem-32 41 30 3.24 3.24 NUM eurjchem-32 41 31     SPACE eurjchem-32 41 32 g g NOUN eurjchem-32 41 33     SPACE eurjchem-32 41 34 ( ( PUNCT eurjchem-32 41 35 70.5 70.5 NUM eurjchem-32 41 36 % % NOUN eurjchem-32 41 37 ) ) PUNCT eurjchem-32 41 38     SPACE eurjchem-32 41 39 of of ADP eurjchem-32 41 40     SPACE eurjchem-32 41 41 14 14 NUM eurjchem-32 41 42 ; ; PUNCT eurjchem-32 41 43     SPACE eurjchem-32 41 44 mp mp PROPN eurjchem-32 41 45     SPACE eurjchem-32 41 46 198‐200 198‐200 PROPN eurjchem-32 41 47     SPACE eurjchem-32 41 48 oc oc NOUN eurjchem-32 41 49 ; ; PUNCT eurjchem-32 41 50     SPACE eurjchem-32 41 51 pale pale ADJ eurjchem-32 41 52     SPACE eurjchem-32 41 53 brown brown ADJ eurjchem-32 41 54     SPACE eurjchem-32 41 55 powder powder NOUN eurjchem-32 41 56 ; ; PUNCT eurjchem-32 41 57     SPACE eurjchem-32 41 58 ir ir PROPN eurjchem-32 41 59     SPACE eurjchem-32 41 60 ( ( PUNCT eurjchem-32 41 61 kbr kbr PROPN eurjchem-32 41 62 ) ) PUNCT eurjchem-32 41 63     SPACE eurjchem-32 41 64 ( ( PUNCT eurjchem-32 41 65 υ υ NOUN eurjchem-32 41 66 , , PUNCT eurjchem-32 41 67     SPACE eurjchem-32 41 68 cm‐1 cm‐1 NOUN eurjchem-32 41 69 ): ): PUNCT eurjchem-32 41 70     SPACE eurjchem-32 41 71 3450 3450 NUM eurjchem-32 41 72     SPACE eurjchem-32 41 73 ( ( PUNCT eurjchem-32 41 74 nh2 nh2 PROPN eurjchem-32 41 75 ) ) PUNCT eurjchem-32 41 76 , , PUNCT eurjchem-32 41 77     SPACE eurjchem-32 41 78 1689 1689 NUM eurjchem-32 41 79     SPACE eurjchem-32 41 80 ( ( PUNCT eurjchem-32 41 81 co co NOUN eurjchem-32 41 82 ) ) PUNCT eurjchem-32 41 83 , , PUNCT eurjchem-32 41 84     SPACE eurjchem-32 41 85 1610 1610 NUM eurjchem-32 41 86     SPACE eurjchem-32 41 87 ( ( PUNCT eurjchem-32 41 88 c c NOUN eurjchem-32 41 89 = = SYM eurjchem-32 41 90 n n NUM eurjchem-32 41 91 ) ) PUNCT eurjchem-32 41 92 . . PUNCT eurjchem-32 41 93     SPACE eurjchem-32 41 94 1h 1h NUM eurjchem-32 41 95     SPACE eurjchem-32 41 96 nmr nmr NOUN eurjchem-32 41 97     SPACE eurjchem-32 41 98 ( ( PUNCT eurjchem-32 41 99 dmso‐d6 dmso‐d6 NOUN eurjchem-32 41 100 ): ): PUNCT eurjchem-32 41 101     SPACE eurjchem-32 41 102 δ δ PROPN eurjchem-32 41 103 , , PUNCT eurjchem-32 41 104     SPACE eurjchem-32 41 105 3.30 3.30 NUM eurjchem-32 41 106     SPACE eurjchem-32 41 107 ( ( PUNCT eurjchem-32 41 108 s s PROPN eurjchem-32 41 109 , , PUNCT eurjchem-32 41 110     SPACE eurjchem-32 41 111 3h 3h NUM eurjchem-32 41 112 , , PUNCT eurjchem-32 41 113     SPACE eurjchem-32 41 114 ch3 ch3 PROPN eurjchem-32 41 115 ) ) PUNCT eurjchem-32 41 116 , , PUNCT eurjchem-32 41 117     SPACE eurjchem-32 41 118 3.35 3.35 NUM eurjchem-32 41 119     SPACE eurjchem-32 41 120 ( ( PUNCT eurjchem-32 41 121 s s PROPN eurjchem-32 41 122 , , PUNCT eurjchem-32 41 123     SPACE eurjchem-32 41 124 3h 3h NUM eurjchem-32 41 125 , , PUNCT eurjchem-32 41 126     SPACE eurjchem-32 41 127 ch3 ch3 PROPN eurjchem-32 41 128 ) ) PUNCT eurjchem-32 41 129 , , PUNCT eurjchem-32 41 130     SPACE eurjchem-32 41 131 6.24 6.24 NUM eurjchem-32 41 132     SPACE eurjchem-32 41 133 ( ( PUNCT eurjchem-32 41 134 s s PROPN eurjchem-32 41 135 , , PUNCT eurjchem-32 41 136     SPACE eurjchem-32 41 137 2h 2h NUM eurjchem-32 41 138 , , PUNCT eurjchem-32 41 139     SPACE eurjchem-32 41 140 nh2 nh2 PROPN eurjchem-32 41 141 ) ) PUNCT eurjchem-32 41 142 , , PUNCT eurjchem-32 41 143     SPACE eurjchem-32 41 144 6.05 6.05 NUM eurjchem-32 41 145     SPACE eurjchem-32 41 146 ( ( PUNCT eurjchem-32 41 147 s s PROPN eurjchem-32 41 148 , , PUNCT eurjchem-32 41 149     SPACE eurjchem-32 41 150 2h 2h NUM eurjchem-32 41 151 , , PUNCT eurjchem-32 41 152     SPACE eurjchem-32 41 153 ch2 ch2 NOUN eurjchem-32 41 154 ) ) PUNCT eurjchem-32 41 155 , , PUNCT eurjchem-32 41 156     SPACE eurjchem-32 41 157 6.9 6.9 NUM eurjchem-32 41 158     SPACE eurjchem-32 41 159 ( ( PUNCT eurjchem-32 41 160 d. d. PROPN eurjchem-32 41 161     SPACE eurjchem-32 41 162 1h 1h NUM eurjchem-32 41 163 , , PUNCT eurjchem-32 41 164     SPACE eurjchem-32 41 165 ch ch NOUN eurjchem-32 41 166 ) ) PUNCT eurjchem-32 41 167 , , PUNCT eurjchem-32 41 168     SPACE eurjchem-32 41 169 7.61 7.61 NUM eurjchem-32 41 170     SPACE eurjchem-32 41 171 ( ( PUNCT eurjchem-32 41 172 s s PROPN eurjchem-32 41 173 , , PUNCT eurjchem-32 41 174     SPACE eurjchem-32 41 175 1h 1h NUM eurjchem-32 41 176 , , PUNCT eurjchem-32 41 177     SPACE eurjchem-32 41 178 ch ch NOUN eurjchem-32 41 179 ) ) PUNCT eurjchem-32 41 180 , , PUNCT eurjchem-32 41 181     SPACE eurjchem-32 41 182 7.7 7.7 NUM eurjchem-32 41 183     SPACE eurjchem-32 41 184 ( ( PUNCT eurjchem-32 41 185 d d NOUN eurjchem-32 41 186 , , PUNCT eurjchem-32 41 187     SPACE eurjchem-32 41 188 1h 1h NUM eurjchem-32 41 189 , , PUNCT eurjchem-32 41 190     SPACE eurjchem-32 41 191 ch ch NOUN eurjchem-32 41 192 ) ) PUNCT eurjchem-32 41 193 , , PUNCT eurjchem-32 41 194     SPACE eurjchem-32 41 195 7.5‐8.2 7.5‐8.2 NOUN eurjchem-32 41 196     SPACE eurjchem-32 41 197 ( ( PUNCT eurjchem-32 41 198 m m PROPN eurjchem-32 41 199 , , PUNCT eurjchem-32 41 200     SPACE eurjchem-32 41 201 4h 4h NOUN eurjchem-32 41 202 , , PUNCT eurjchem-32 41 203     SPACE eurjchem-32 41 204 ar‐h ar‐h NOUN eurjchem-32 41 205 ) ) PUNCT eurjchem-32 41 206 . . PUNCT eurjchem-32 41 207     SPACE eurjchem-32 42 1 ms ms NOUN eurjchem-32 42 2 : : PUNCT eurjchem-32 42 3     SPACE eurjchem-32 42 4 ( ( PUNCT eurjchem-32 42 5 m m PROPN eurjchem-32 42 6 / / SYM eurjchem-32 42 7 z z NOUN eurjchem-32 42 8 , , PUNCT eurjchem-32 42 9     SPACE eurjchem-32 42 10 % % NOUN eurjchem-32 42 11 ): ): PUNCT eurjchem-32 42 12     SPACE eurjchem-32 42 13 459 459 NUM eurjchem-32 42 14     SPACE eurjchem-32 42 15 ( ( PUNCT eurjchem-32 42 16 m+ m+ NUM eurjchem-32 42 17 , , PUNCT eurjchem-32 42 18     SPACE eurjchem-32 42 19 13 13 NUM eurjchem-32 42 20 ) ) PUNCT eurjchem-32 42 21 . . PUNCT eurjchem-32 42 22     SPACE eurjchem-32 43 1 anal anal ADJ eurjchem-32 43 2 . . PUNCT eurjchem-32 43 3     SPACE eurjchem-32 43 4 calcd calcd NOUN eurjchem-32 43 5 . . PUNCT eurjchem-32 43 6     SPACE eurjchem-32 43 7 for for ADP eurjchem-32 43 8     SPACE eurjchem-32 43 9 c23h17n5o4s c23h17n5o4s NUM eurjchem-32 43 10 : : PUNCT eurjchem-32 43 11     SPACE eurjchem-32 43 12 c c X eurjchem-32 43 13 , , PUNCT eurjchem-32 43 14     SPACE eurjchem-32 43 15 60.12 60.12 NUM eurjchem-32 43 16 ; ; PUNCT eurjchem-32 43 17     SPACE eurjchem-32 43 18 h h NOUN eurjchem-32 43 19 , , PUNCT eurjchem-32 43 20     SPACE eurjchem-32 43 21 3.73 3.73 NUM eurjchem-32 43 22 ; ; PUNCT eurjchem-32 43 23     SPACE eurjchem-32 43 24 n n CCONJ eurjchem-32 43 25 , , PUNCT eurjchem-32 43 26     SPACE eurjchem-32 43 27 15.24 15.24 NUM eurjchem-32 43 28 . . PUNCT eurjchem-32 43 29     SPACE eurjchem-32 43 30 found find VERB eurjchem-32 43 31 : : PUNCT eurjchem-32 43 32     SPACE eurjchem-32 43 33 c c X eurjchem-32 43 34 , , PUNCT eurjchem-32 43 35     SPACE eurjchem-32 43 36 60.20 60.20 NUM eurjchem-32 43 37 ; ; PUNCT eurjchem-32 43 38     SPACE eurjchem-32 43 39 h h NOUN eurjchem-32 43 40 , , PUNCT eurjchem-32 43 41     SPACE eurjchem-32 43 42 3.78 3.78 NUM eurjchem-32 43 43 ; ; PUNCT eurjchem-32 43 44     SPACE eurjchem-32 43 45 n n CCONJ eurjchem-32 43 46 , , PUNCT eurjchem-32 43 47     SPACE eurjchem-32 43 48 15.31 15.31 NUM eurjchem-32 43 49 . . PUNCT eurjchem-32 43 50                     SPACE eurjchem-32 44 1 92 92 NUM eurjchem-32 44 2     SPACE eurjchem-32 44 3 fadda fadda NOUN eurjchem-32 44 4     SPACE eurjchem-32 44 5 et et PROPN eurjchem-32 44 6     SPACE eurjchem-32 44 7 al al PROPN eurjchem-32 44 8 . . PROPN eurjchem-32 44 9     SPACE eurjchem-32 44 10 / / SYM eurjchem-32 44 11     SPACE eurjchem-32 44 12 european european ADJ eurjchem-32 44 13     SPACE eurjchem-32 44 14 journal journal NOUN eurjchem-32 44 15     SPACE eurjchem-32 44 16 of of ADP eurjchem-32 44 17     SPACE eurjchem-32 44 18 chemistry chemistry NOUN eurjchem-32 44 19     SPACE eurjchem-32 44 20 1 1 NUM eurjchem-32 44 21     SPACE eurjchem-32 44 22 ( ( PUNCT eurjchem-32 44 23 2 2 NUM eurjchem-32 44 24 ) ) PUNCT eurjchem-32 44 25     SPACE eurjchem-32 44 26 ( ( PUNCT eurjchem-32 44 27 2010 2010 NUM eurjchem-32 44 28 ) ) PUNCT eurjchem-32 44 29     SPACE eurjchem-32 44 30 90­95 90­95 NUM eurjchem-32 44 31         SPACE eurjchem-32 44 32 scheme scheme NOUN eurjchem-32 44 33     SPACE eurjchem-32 44 34 6 6 NUM eurjchem-32 44 35             SPACE eurjchem-32 44 36 2.6 2.6 NUM eurjchem-32 44 37 . . PUNCT eurjchem-32 44 38     SPACE eurjchem-32 45 1 2­(benzo[d]thiazol­2­yl)­4­(4­methylbenzylidene)­3­oxo­ 2­(benzo[d]thiazol­2­yl)­4­(4­methylbenzylidene)­3­oxo­ NUM eurjchem-32 45 2 pentanedinitrile pentanedinitrile ADJ eurjchem-32 45 3 , , PUNCT eurjchem-32 45 4     SPACE eurjchem-32 45 5 15 15 NUM eurjchem-32 45 6           SPACE eurjchem-32 45 7 a a DET eurjchem-32 45 8     SPACE eurjchem-32 45 9 mixture mixture NOUN eurjchem-32 45 10     SPACE eurjchem-32 45 11 of of ADP eurjchem-32 45 12     SPACE eurjchem-32 45 13 4 4 NUM eurjchem-32 45 14     SPACE eurjchem-32 45 15 ( ( PUNCT eurjchem-32 45 16 2.41 2.41 NUM eurjchem-32 45 17     SPACE eurjchem-32 45 18 g g NOUN eurjchem-32 45 19 , , PUNCT eurjchem-32 45 20     SPACE eurjchem-32 45 21 0.01 0.01 NUM eurjchem-32 45 22     SPACE eurjchem-32 45 23 mol mol NOUN eurjchem-32 45 24 ) ) PUNCT eurjchem-32 45 25 , , PUNCT eurjchem-32 45 26     SPACE eurjchem-32 45 27 p‐tolualdehyde p‐tolualdehyde SYM eurjchem-32 45 28     SPACE eurjchem-32 45 29 ( ( PUNCT eurjchem-32 45 30 1.20 1.20 NUM eurjchem-32 45 31     SPACE eurjchem-32 45 32 g g NOUN eurjchem-32 45 33 , , PUNCT eurjchem-32 45 34     SPACE eurjchem-32 45 35 0.01 0.01 NUM eurjchem-32 45 36     SPACE eurjchem-32 45 37 mol mol NOUN eurjchem-32 45 38 ) ) PUNCT eurjchem-32 45 39     SPACE eurjchem-32 45 40 and and CCONJ eurjchem-32 45 41     SPACE eurjchem-32 45 42 freshly freshly ADV eurjchem-32 45 43     SPACE eurjchem-32 45 44 fused fuse VERB eurjchem-32 45 45     SPACE eurjchem-32 45 46 sodium sodium NOUN eurjchem-32 45 47     SPACE eurjchem-32 45 48 acetate acetate NOUN eurjchem-32 45 49     SPACE eurjchem-32 45 50 ( ( PUNCT eurjchem-32 45 51 1.23 1.23 NUM eurjchem-32 45 52     SPACE eurjchem-32 45 53 g g NOUN eurjchem-32 45 54 , , PUNCT eurjchem-32 45 55     SPACE eurjchem-32 45 56 0.015 0.015 NUM eurjchem-32 45 57     SPACE eurjchem-32 45 58 mol mol NOUN eurjchem-32 45 59 ) ) PUNCT eurjchem-32 45 60     SPACE eurjchem-32 45 61 in in ADP eurjchem-32 45 62     SPACE eurjchem-32 45 63 glacial glacial ADJ eurjchem-32 45 64     SPACE eurjchem-32 45 65 acetic acetic ADJ eurjchem-32 45 66     SPACE eurjchem-32 45 67 acid acid NOUN eurjchem-32 45 68     SPACE eurjchem-32 45 69 ( ( PUNCT eurjchem-32 45 70 15 15 NUM eurjchem-32 45 71     SPACE eurjchem-32 45 72 ml ml NOUN eurjchem-32 45 73 ) ) PUNCT eurjchem-32 45 74     SPACE eurjchem-32 45 75 was be AUX eurjchem-32 45 76     SPACE eurjchem-32 45 77 refluxed refluxe VERB eurjchem-32 45 78     SPACE eurjchem-32 45 79 for for ADP eurjchem-32 45 80     SPACE eurjchem-32 45 81 4 4 NUM eurjchem-32 45 82     SPACE eurjchem-32 45 83 h h NOUN eurjchem-32 45 84     SPACE eurjchem-32 45 85 over over ADP eurjchem-32 45 86     SPACE eurjchem-32 45 87 a a DET eurjchem-32 45 88     SPACE eurjchem-32 45 89 water water NOUN eurjchem-32 45 90     SPACE eurjchem-32 45 91 bath bath NOUN eurjchem-32 45 92     SPACE eurjchem-32 45 93 ( ( PUNCT eurjchem-32 45 94 scheme scheme NOUN eurjchem-32 45 95     SPACE eurjchem-32 45 96 7 7 NUM eurjchem-32 45 97 ) ) PUNCT eurjchem-32 45 98 . . PUNCT eurjchem-32 45 99     SPACE eurjchem-32 46 1 the the DET eurjchem-32 46 2     SPACE eurjchem-32 46 3 precipitated precipitate VERB eurjchem-32 46 4     SPACE eurjchem-32 46 5 solid solid ADJ eurjchem-32 46 6     SPACE eurjchem-32 46 7 was be AUX eurjchem-32 46 8     SPACE eurjchem-32 46 9 filtered filter VERB eurjchem-32 46 10     SPACE eurjchem-32 46 11 and and CCONJ eurjchem-32 46 12     SPACE eurjchem-32 46 13 recrystallized recrystallize VERB eurjchem-32 46 14     SPACE eurjchem-32 46 15 from from ADP eurjchem-32 46 16     SPACE eurjchem-32 46 17 ethanol ethanol NOUN eurjchem-32 46 18     SPACE eurjchem-32 46 19 to to PART eurjchem-32 46 20     SPACE eurjchem-32 46 21 give give VERB eurjchem-32 46 22     SPACE eurjchem-32 46 23 2.37 2.37 NUM eurjchem-32 46 24     SPACE eurjchem-32 46 25 g g NOUN eurjchem-32 46 26     SPACE eurjchem-32 46 27 ( ( PUNCT eurjchem-32 46 28 69 69 NUM eurjchem-32 46 29 % % NOUN eurjchem-32 46 30 ) ) PUNCT eurjchem-32 46 31     SPACE eurjchem-32 46 32 of of ADP eurjchem-32 46 33     SPACE eurjchem-32 46 34 15 15 NUM eurjchem-32 46 35 ; ; PUNCT eurjchem-32 46 36     SPACE eurjchem-32 46 37 mp mp NOUN eurjchem-32 46 38     SPACE eurjchem-32 46 39 246 246 NUM eurjchem-32 46 40     SPACE eurjchem-32 46 41 oc oc NOUN eurjchem-32 46 42 ; ; PUNCT eurjchem-32 46 43     SPACE eurjchem-32 46 44 ir ir PROPN eurjchem-32 46 45     SPACE eurjchem-32 46 46 ( ( PUNCT eurjchem-32 46 47 kbr kbr PROPN eurjchem-32 46 48 ) ) PUNCT eurjchem-32 46 49     SPACE eurjchem-32 46 50 ( ( PUNCT eurjchem-32 46 51 υ υ NOUN eurjchem-32 46 52 , , PUNCT eurjchem-32 46 53     SPACE eurjchem-32 46 54 cm‐1 cm‐1 NOUN eurjchem-32 46 55 ): ): PUNCT eurjchem-32 46 56     SPACE eurjchem-32 46 57 2220 2220 NUM eurjchem-32 46 58     SPACE eurjchem-32 46 59 ( ( PUNCT eurjchem-32 46 60 cn cn PROPN eurjchem-32 46 61 ) ) PUNCT eurjchem-32 46 62 , , PUNCT eurjchem-32 46 63     SPACE eurjchem-32 46 64 1630 1630 NUM eurjchem-32 46 65     SPACE eurjchem-32 46 66 ( ( PUNCT eurjchem-32 46 67 co co NOUN eurjchem-32 46 68 ) ) PUNCT eurjchem-32 46 69 , , PUNCT eurjchem-32 46 70     SPACE eurjchem-32 46 71 1513 1513 NUM eurjchem-32 46 72     SPACE eurjchem-32 46 73 ( ( PUNCT eurjchem-32 46 74 c c NOUN eurjchem-32 46 75 = = SYM eurjchem-32 46 76 n n NUM eurjchem-32 46 77 ) ) PUNCT eurjchem-32 46 78 . . PUNCT eurjchem-32 46 79     SPACE eurjchem-32 46 80 1h 1h NUM eurjchem-32 46 81     SPACE eurjchem-32 46 82 nmr nmr NOUN eurjchem-32 46 83     SPACE eurjchem-32 46 84 ( ( PUNCT eurjchem-32 46 85 dmso‐d6 dmso‐d6 NOUN eurjchem-32 46 86 ): ): PUNCT eurjchem-32 46 87     SPACE eurjchem-32 46 88 δ δ PROPN eurjchem-32 46 89 , , PUNCT eurjchem-32 46 90     SPACE eurjchem-32 46 91 2.49 2.49 NUM eurjchem-32 46 92     SPACE eurjchem-32 46 93 ( ( PUNCT eurjchem-32 46 94 s s PROPN eurjchem-32 46 95 , , PUNCT eurjchem-32 46 96     SPACE eurjchem-32 46 97 3h 3h NUM eurjchem-32 46 98 , , PUNCT eurjchem-32 46 99     SPACE eurjchem-32 46 100 ch3 ch3 PROPN eurjchem-32 46 101 ) ) PUNCT eurjchem-32 46 102 , , PUNCT eurjchem-32 46 103     SPACE eurjchem-32 46 104 5.70 5.70 NUM eurjchem-32 46 105     SPACE eurjchem-32 46 106 ( ( PUNCT eurjchem-32 46 107 s s PROPN eurjchem-32 46 108 , , PUNCT eurjchem-32 46 109     SPACE eurjchem-32 46 110 1h 1h NUM eurjchem-32 46 111 , , PUNCT eurjchem-32 46 112     SPACE eurjchem-32 46 113 methine methine ADJ eurjchem-32 46 114     SPACE eurjchem-32 46 115 proton proton NOUN eurjchem-32 46 116 ) ) PUNCT eurjchem-32 46 117 , , PUNCT eurjchem-32 46 118     SPACE eurjchem-32 46 119 6.30 6.30 NUM eurjchem-32 46 120     SPACE eurjchem-32 46 121 ( ( PUNCT eurjchem-32 46 122 s s PROPN eurjchem-32 46 123 , , PUNCT eurjchem-32 46 124     SPACE eurjchem-32 46 125 1h 1h NUM eurjchem-32 46 126 , , PUNCT eurjchem-32 46 127     SPACE eurjchem-32 46 128 vinylic vinylic ADJ eurjchem-32 46 129     SPACE eurjchem-32 46 130 proton proton NOUN eurjchem-32 46 131 ) ) PUNCT eurjchem-32 46 132 , , PUNCT eurjchem-32 46 133     SPACE eurjchem-32 46 134 7.19‐8.10 7.19‐8.10 NOUN eurjchem-32 46 135     SPACE eurjchem-32 46 136 ( ( PUNCT eurjchem-32 46 137 m m PROPN eurjchem-32 46 138 , , PUNCT eurjchem-32 46 139     SPACE eurjchem-32 46 140 8h 8h NUM eurjchem-32 46 141 , , PUNCT eurjchem-32 46 142     SPACE eurjchem-32 46 143 ar‐h ar‐h NOUN eurjchem-32 46 144 ) ) PUNCT eurjchem-32 46 145 . . PUNCT eurjchem-32 46 146     SPACE eurjchem-32 47 1 ms ms NOUN eurjchem-32 47 2 : : PUNCT eurjchem-32 47 3     SPACE eurjchem-32 47 4 ( ( PUNCT eurjchem-32 47 5 m m PROPN eurjchem-32 47 6 / / SYM eurjchem-32 47 7 z z NOUN eurjchem-32 47 8 , , PUNCT eurjchem-32 47 9     SPACE eurjchem-32 47 10 % % NOUN eurjchem-32 47 11 ): ): PUNCT eurjchem-32 47 12     SPACE eurjchem-32 47 13 343 343 NUM eurjchem-32 47 14     SPACE eurjchem-32 47 15 ( ( PUNCT eurjchem-32 47 16 m+ m+ NUM eurjchem-32 47 17 , , PUNCT eurjchem-32 47 18     SPACE eurjchem-32 47 19 5 5 NUM eurjchem-32 47 20 ) ) PUNCT eurjchem-32 47 21 . . PUNCT eurjchem-32 47 22     SPACE eurjchem-32 48 1 anal anal ADJ eurjchem-32 48 2 . . PUNCT eurjchem-32 48 3     SPACE eurjchem-32 48 4 calcd calcd NOUN eurjchem-32 48 5 . . PUNCT eurjchem-32 48 6     SPACE eurjchem-32 48 7 for for ADP eurjchem-32 48 8     SPACE eurjchem-32 48 9 c20h13n3os c20h13n3os NOUN eurjchem-32 48 10 : : PUNCT eurjchem-32 48 11     SPACE eurjchem-32 48 12 c c X eurjchem-32 48 13 , , PUNCT eurjchem-32 48 14     SPACE eurjchem-32 48 15 69.95 69.95 NUM eurjchem-32 48 16 ; ; PUNCT eurjchem-32 48 17     SPACE eurjchem-32 48 18 h h NOUN eurjchem-32 48 19 , , PUNCT eurjchem-32 48 20     SPACE eurjchem-32 48 21 3.82 3.82 NUM eurjchem-32 48 22 ; ; PUNCT eurjchem-32 48 23     SPACE eurjchem-32 48 24 n n CCONJ eurjchem-32 48 25 , , PUNCT eurjchem-32 48 26     SPACE eurjchem-32 48 27 12.24 12.24 NUM eurjchem-32 48 28 . . PUNCT eurjchem-32 48 29     SPACE eurjchem-32 48 30 found find VERB eurjchem-32 48 31 : : PUNCT eurjchem-32 48 32     SPACE eurjchem-32 48 33 c c X eurjchem-32 48 34 , , PUNCT eurjchem-32 48 35     SPACE eurjchem-32 48 36 70.02 70.02 NUM eurjchem-32 48 37 ; ; PUNCT eurjchem-32 48 38     SPACE eurjchem-32 48 39 h h NOUN eurjchem-32 48 40 , , PUNCT eurjchem-32 48 41     SPACE eurjchem-32 48 42 3.87 3.87 NUM eurjchem-32 48 43 ; ; PUNCT eurjchem-32 48 44     SPACE eurjchem-32 48 45 n n CCONJ eurjchem-32 48 46 , , PUNCT eurjchem-32 48 47     SPACE eurjchem-32 48 48 12.31 12.31 NUM eurjchem-32 48 49 . . PUNCT eurjchem-32 48 50         SPACE eurjchem-32 48 51 scheme scheme NOUN eurjchem-32 48 52     SPACE eurjchem-32 48 53 7 7 NUM eurjchem-32 48 54         SPACE eurjchem-32 48 55 2.7 2.7 NUM eurjchem-32 48 56 . . PUNCT eurjchem-32 48 57     SPACE eurjchem-32 49 1 2­amino­3­(benzo[d]thiazol­2­yl)­4h­chromeno[2,3­ 2­amino­3­(benzo[d]thiazol­2­yl)­4h­chromeno[2,3­ NUM eurjchem-32 49 2 b]pyridin­4­one b]pyridin­4­one NUM eurjchem-32 49 3 , , PUNCT eurjchem-32 49 4     SPACE eurjchem-32 49 5 16 16 NUM eurjchem-32 49 6           SPACE eurjchem-32 49 7 a a DET eurjchem-32 49 8     SPACE eurjchem-32 49 9 mixture mixture NOUN eurjchem-32 49 10     SPACE eurjchem-32 49 11 of of ADP eurjchem-32 49 12     SPACE eurjchem-32 49 13 4 4 NUM eurjchem-32 49 14     SPACE eurjchem-32 49 15 ( ( PUNCT eurjchem-32 49 16 2.41 2.41 NUM eurjchem-32 49 17     SPACE eurjchem-32 49 18 g g NOUN eurjchem-32 49 19 , , PUNCT eurjchem-32 49 20     SPACE eurjchem-32 49 21 0.01 0.01 NUM eurjchem-32 49 22     SPACE eurjchem-32 49 23 mol mol NOUN eurjchem-32 49 24 ) ) PUNCT eurjchem-32 49 25 , , PUNCT eurjchem-32 49 26     SPACE eurjchem-32 49 27 salicylaldehyde salicylaldehyde NOUN eurjchem-32 49 28     SPACE eurjchem-32 49 29 ( ( PUNCT eurjchem-32 49 30 1.22 1.22 NUM eurjchem-32 49 31     SPACE eurjchem-32 49 32 g g NOUN eurjchem-32 49 33 , , PUNCT eurjchem-32 49 34     SPACE eurjchem-32 49 35 0.01 0.01 NUM eurjchem-32 49 36     SPACE eurjchem-32 49 37 mol mol NOUN eurjchem-32 49 38 ) ) PUNCT eurjchem-32 49 39     SPACE eurjchem-32 49 40 in in ADP eurjchem-32 49 41     SPACE eurjchem-32 49 42 ethanol ethanol NOUN eurjchem-32 49 43     SPACE eurjchem-32 49 44 ( ( PUNCT eurjchem-32 49 45 15 15 NUM eurjchem-32 49 46     SPACE eurjchem-32 49 47 ml ml NOUN eurjchem-32 49 48 ) ) PUNCT eurjchem-32 49 49     SPACE eurjchem-32 49 50 containing contain VERB eurjchem-32 49 51     SPACE eurjchem-32 49 52 a a DET eurjchem-32 49 53     SPACE eurjchem-32 49 54 catalytic catalytic ADJ eurjchem-32 49 55     SPACE eurjchem-32 49 56 amounts amount NOUN eurjchem-32 49 57     SPACE eurjchem-32 49 58 of of ADP eurjchem-32 49 59     SPACE eurjchem-32 49 60 piperidine piperidine NOUN eurjchem-32 49 61     SPACE eurjchem-32 49 62 was be AUX eurjchem-32 49 63     SPACE eurjchem-32 49 64 refluxed refluxe VERB eurjchem-32 49 65     SPACE eurjchem-32 49 66 for for ADP eurjchem-32 49 67     SPACE eurjchem-32 49 68 4 4 NUM eurjchem-32 49 69     SPACE eurjchem-32 49 70 h. h. NOUN eurjchem-32 49 71     SPACE eurjchem-32 49 72 left leave VERB eurjchem-32 49 73     SPACE eurjchem-32 49 74 to to PART eurjchem-32 49 75     SPACE eurjchem-32 49 76 cool cool VERB eurjchem-32 49 77     SPACE eurjchem-32 49 78 at at ADP eurjchem-32 49 79     SPACE eurjchem-32 49 80 room room NOUN eurjchem-32 49 81     SPACE eurjchem-32 49 82 tempe‐ tempe‐ PUNCT eurjchem-32 49 83 rature rature NOUN eurjchem-32 49 84     SPACE eurjchem-32 49 85 and and CCONJ eurjchem-32 49 86     SPACE eurjchem-32 49 87 poured pour VERB eurjchem-32 49 88     SPACE eurjchem-32 49 89 into into ADP eurjchem-32 49 90     SPACE eurjchem-32 49 91 ice ice NOUN eurjchem-32 49 92     SPACE eurjchem-32 49 93 cold cold ADJ eurjchem-32 49 94     SPACE eurjchem-32 49 95 water water NOUN eurjchem-32 49 96     SPACE eurjchem-32 49 97 ( ( PUNCT eurjchem-32 49 98 scheme scheme NOUN eurjchem-32 49 99     SPACE eurjchem-32 49 100 8) 8) NUM eurjchem-32 49 101 . . PUNCT eurjchem-32 49 102     SPACE eurjchem-32 49 103 the the DET eurjchem-32 49 104     SPACE eurjchem-32 49 105 solid solid ADJ eurjchem-32 49 106     SPACE eurjchem-32 49 107 product product NOUN eurjchem-32 49 108     SPACE eurjchem-32 49 109 obtained obtain VERB eurjchem-32 49 110     SPACE eurjchem-32 49 111 was be AUX eurjchem-32 49 112     SPACE eurjchem-32 49 113 filtered filter VERB eurjchem-32 49 114     SPACE eurjchem-32 49 115 off off ADP eurjchem-32 49 116 , , PUNCT eurjchem-32 49 117     SPACE eurjchem-32 49 118 dried dry VERB eurjchem-32 49 119     SPACE eurjchem-32 49 120 and and CCONJ eurjchem-32 49 121     SPACE eurjchem-32 49 122 recrystallized recrystallize VERB eurjchem-32 49 123     SPACE eurjchem-32 49 124 from from ADP eurjchem-32 49 125     SPACE eurjchem-32 49 126 ethanol ethanol NOUN eurjchem-32 49 127     SPACE eurjchem-32 49 128 affording afford VERB eurjchem-32 49 129     SPACE eurjchem-32 49 130 3.0 3.0 NUM eurjchem-32 49 131     SPACE eurjchem-32 49 132 g g NOUN eurjchem-32 49 133     SPACE eurjchem-32 49 134 ( ( PUNCT eurjchem-32 49 135 87 87 NUM eurjchem-32 49 136 % % NOUN eurjchem-32 49 137 ) ) PUNCT eurjchem-32 49 138     SPACE eurjchem-32 49 139 of of ADP eurjchem-32 49 140     SPACE eurjchem-32 49 141 16 16 NUM eurjchem-32 49 142 ; ; PUNCT eurjchem-32 49 143     SPACE eurjchem-32 49 144 mp mp NOUN eurjchem-32 49 145     SPACE eurjchem-32 49 146 > > NOUN eurjchem-32 49 147     SPACE eurjchem-32 49 148 300 300 NUM eurjchem-32 49 149     SPACE eurjchem-32 49 150 oc oc NOUN eurjchem-32 49 151 ; ; PUNCT eurjchem-32 49 152     SPACE eurjchem-32 49 153 red red ADJ eurjchem-32 49 154     SPACE eurjchem-32 49 155 crystal crystal NOUN eurjchem-32 49 156 ; ; PUNCT eurjchem-32 49 157     SPACE eurjchem-32 49 158 ir ir PROPN eurjchem-32 49 159     SPACE eurjchem-32 49 160 ( ( PUNCT eurjchem-32 49 161 kbr kbr PROPN eurjchem-32 49 162 ) ) PUNCT eurjchem-32 49 163     SPACE eurjchem-32 49 164 ( ( PUNCT eurjchem-32 49 165 υ υ NOUN eurjchem-32 49 166 , , PUNCT eurjchem-32 49 167     SPACE eurjchem-32 49 168 cm‐1 cm‐1 NOUN eurjchem-32 49 169 ): ): PUNCT eurjchem-32 49 170     SPACE eurjchem-32 49 171 3300‐3400 3300‐3400 NUM eurjchem-32 49 172     SPACE eurjchem-32 49 173 ( ( PUNCT eurjchem-32 49 174 nh2 nh2 PROPN eurjchem-32 49 175 ) ) PUNCT eurjchem-32 49 176 , , PUNCT eurjchem-32 49 177     SPACE eurjchem-32 49 178 1642 1642 NUM eurjchem-32 49 179     SPACE eurjchem-32 49 180 ( ( PUNCT eurjchem-32 49 181 co co NOUN eurjchem-32 49 182 ) ) PUNCT eurjchem-32 49 183 . . PUNCT eurjchem-32 49 184     SPACE eurjchem-32 49 185 1h 1h NUM eurjchem-32 49 186     SPACE eurjchem-32 49 187 nmr nmr NOUN eurjchem-32 49 188     SPACE eurjchem-32 49 189 ( ( PUNCT eurjchem-32 49 190 dmso‐d6 dmso‐d6 NOUN eurjchem-32 49 191 ): ): PUNCT eurjchem-32 49 192     SPACE eurjchem-32 49 193 δ δ PROPN eurjchem-32 49 194 , , PUNCT eurjchem-32 49 195     SPACE eurjchem-32 49 196 6.93‐8.16 6.93‐8.16 NOUN eurjchem-32 49 197     SPACE eurjchem-32 49 198 ( ( PUNCT eurjchem-32 49 199 m m PROPN eurjchem-32 49 200 , , PUNCT eurjchem-32 49 201     SPACE eurjchem-32 49 202 8h 8h NUM eurjchem-32 49 203 , , PUNCT eurjchem-32 49 204     SPACE eurjchem-32 49 205 ar‐h ar‐h NOUN eurjchem-32 49 206 ) ) PUNCT eurjchem-32 49 207 , , PUNCT eurjchem-32 49 208     SPACE eurjchem-32 49 209 8.60 8.60 NUM eurjchem-32 49 210     SPACE eurjchem-32 49 211 ( ( PUNCT eurjchem-32 49 212 s s PROPN eurjchem-32 49 213 , , PUNCT eurjchem-32 49 214     SPACE eurjchem-32 49 215 2h 2h NUM eurjchem-32 49 216 , , PUNCT eurjchem-32 49 217     SPACE eurjchem-32 49 218 nh2 nh2 PROPN eurjchem-32 49 219 ) ) PUNCT eurjchem-32 49 220 , , PUNCT eurjchem-32 49 221     SPACE eurjchem-32 49 222 8.77 8.77 NUM eurjchem-32 49 223     SPACE eurjchem-32 49 224 ( ( PUNCT eurjchem-32 49 225 s s PROPN eurjchem-32 49 226 , , PUNCT eurjchem-32 49 227     SPACE eurjchem-32 49 228 c4‐h c4‐h NOUN eurjchem-32 49 229 , , PUNCT eurjchem-32 49 230     SPACE eurjchem-32 49 231 pyran pyran ADJ eurjchem-32 49 232 ) ) PUNCT eurjchem-32 49 233 . . PUNCT eurjchem-32 49 234     SPACE eurjchem-32 50 1 ms ms NOUN eurjchem-32 50 2 : : PUNCT eurjchem-32 50 3     SPACE eurjchem-32 50 4 ( ( PUNCT eurjchem-32 50 5 m m PROPN eurjchem-32 50 6 / / SYM eurjchem-32 50 7 z z NOUN eurjchem-32 50 8 , , PUNCT eurjchem-32 50 9     SPACE eurjchem-32 50 10 % % NOUN eurjchem-32 50 11 ): ): PUNCT eurjchem-32 50 12     SPACE eurjchem-32 50 13 345 345 NUM eurjchem-32 50 14     SPACE eurjchem-32 50 15 ( ( PUNCT eurjchem-32 50 16 m+ m+ NUM eurjchem-32 50 17 , , PUNCT eurjchem-32 50 18     SPACE eurjchem-32 50 19 100.0 100.0 NUM eurjchem-32 50 20 ) ) PUNCT eurjchem-32 50 21 , , PUNCT eurjchem-32 50 22     SPACE eurjchem-32 50 23 159 159 NUM eurjchem-32 50 24     SPACE eurjchem-32 50 25 ( ( PUNCT eurjchem-32 50 26 39.2 39.2 NUM eurjchem-32 50 27 ) ) PUNCT eurjchem-32 50 28 , , PUNCT eurjchem-32 50 29     SPACE eurjchem-32 50 30 118 118 NUM eurjchem-32 50 31     SPACE eurjchem-32 50 32 ( ( PUNCT eurjchem-32 50 33 21.1 21.1 NUM eurjchem-32 50 34 ) ) PUNCT eurjchem-32 50 35 , , PUNCT eurjchem-32 50 36     SPACE eurjchem-32 50 37 63 63 NUM eurjchem-32 50 38     SPACE eurjchem-32 50 39 ( ( PUNCT eurjchem-32 50 40 43.5 43.5 NUM eurjchem-32 50 41 ) ) PUNCT eurjchem-32 50 42 . . PUNCT eurjchem-32 50 43     SPACE eurjchem-32 51 1 anal anal ADJ eurjchem-32 51 2 . . PUNCT eurjchem-32 51 3     SPACE eurjchem-32 51 4 calcd calcd NOUN eurjchem-32 51 5 . . PUNCT eurjchem-32 51 6     SPACE eurjchem-32 51 7 for for ADP eurjchem-32 51 8     SPACE eurjchem-32 51 9 c19h11n3o2s c19h11n3o2s PROPN eurjchem-32 51 10 : : PUNCT eurjchem-32 51 11     SPACE eurjchem-32 51 12 c c X eurjchem-32 51 13 , , PUNCT eurjchem-32 51 14     SPACE eurjchem-32 51 15 66.07 66.07 NUM eurjchem-32 51 16 ; ; PUNCT eurjchem-32 51 17     SPACE eurjchem-32 51 18 h h NOUN eurjchem-32 51 19 , , PUNCT eurjchem-32 51 20     SPACE eurjchem-32 51 21 3.21 3.21 NUM eurjchem-32 51 22 ; ; PUNCT eurjchem-32 51 23     SPACE eurjchem-32 51 24 n n CCONJ eurjchem-32 51 25 , , PUNCT eurjchem-32 51 26     SPACE eurjchem-32 51 27 12.17 12.17 NUM eurjchem-32 51 28 . . PUNCT eurjchem-32 51 29     SPACE eurjchem-32 51 30 found find VERB eurjchem-32 51 31 : : PUNCT eurjchem-32 51 32     SPACE eurjchem-32 51 33 c c X eurjchem-32 51 34 , , PUNCT eurjchem-32 51 35     SPACE eurjchem-32 51 36 66.14 66.14 NUM eurjchem-32 51 37 ; ; PUNCT eurjchem-32 51 38     SPACE eurjchem-32 51 39 h h NOUN eurjchem-32 51 40 , , PUNCT eurjchem-32 51 41     SPACE eurjchem-32 51 42 3.27 3.27 NUM eurjchem-32 51 43 ; ; PUNCT eurjchem-32 51 44     SPACE eurjchem-32 51 45 n n CCONJ eurjchem-32 51 46 , , PUNCT eurjchem-32 51 47     SPACE eurjchem-32 51 48 12.23 12.23 NUM eurjchem-32 51 49 . . PUNCT eurjchem-32 51 50         SPACE eurjchem-32 51 51 s s PART eurjchem-32 52 1 n n VERB eurjchem-32 53 1 cn cn INTJ eurjchem-32 53 2 cn cn PROPN eurjchem-32 53 3 o o NOUN eurjchem-32 53 4 4 4 NUM eurjchem-32 53 5 etoh etoh NOUN eurjchem-32 53 6 piperidine piperidine NOUN eurjchem-32 53 7 s s VERB eurjchem-32 53 8 n n INTJ eurjchem-32 54 1 cn cn INTJ eurjchem-32 54 2 cn cn INTJ eurjchem-32 55 1 o o NOUN eurjchem-32 55 2 ch ch NOUN eurjchem-32 56 1 + + CCONJ eurjchem-32 56 2 cho cho NOUN eurjchem-32 57 1 oh oh INTJ eurjchem-32 57 2 oh oh INTJ eurjchem-32 57 3 s s VERB eurjchem-32 57 4 n n PRON eurjchem-32 57 5 o o NOUN eurjchem-32 57 6 o o X eurjchem-32 58 1 nh nh INTJ eurjchem-32 59 1 cn cn PROPN eurjchem-32 59 2 s s PROPN eurjchem-32 59 3 n n PRON eurjchem-32 59 4 o o NOUN eurjchem-32 59 5 o o NOUN eurjchem-32 59 6 n n CCONJ eurjchem-32 59 7 nh2 nh2 PROPN eurjchem-32 59 8 16 16 NUM eurjchem-32 59 9 scheme scheme NOUN eurjchem-32 59 10     SPACE eurjchem-32 59 11 8 8 NUM eurjchem-32 59 12                 SPACE eurjchem-32 59 13 2.8 2.8 NUM eurjchem-32 59 14 . . PUNCT eurjchem-32 59 15     SPACE eurjchem-32 60 1 2­amino­3­(benzo[d]thiazol­2­yl)­benzo[5,6]­4h­ 2­amino­3­(benzo[d]thiazol­2­yl)­benzo[5,6]­4h­ NUM eurjchem-32 60 2 chromeno[2,3­b]pyridin­4­one chromeno[2,3­b]pyridin­4­one NOUN eurjchem-32 60 3 , , PUNCT eurjchem-32 60 4     SPACE eurjchem-32 60 5 17 17 NUM eurjchem-32 60 6           SPACE eurjchem-32 60 7 a a DET eurjchem-32 60 8     SPACE eurjchem-32 60 9 mixture mixture NOUN eurjchem-32 60 10     SPACE eurjchem-32 60 11 of of ADP eurjchem-32 60 12     SPACE eurjchem-32 60 13 4 4 NUM eurjchem-32 60 14     SPACE eurjchem-32 60 15 ( ( PUNCT eurjchem-32 60 16 2.41 2.41 NUM eurjchem-32 60 17     SPACE eurjchem-32 60 18 g g NOUN eurjchem-32 60 19 , , PUNCT eurjchem-32 60 20     SPACE eurjchem-32 60 21 0.01 0.01 NUM eurjchem-32 60 22     SPACE eurjchem-32 60 23 mol mol NOUN eurjchem-32 60 24 ) ) PUNCT eurjchem-32 60 25     SPACE eurjchem-32 60 26 and and CCONJ eurjchem-32 60 27     SPACE eurjchem-32 60 28 2‐hydroxy‐1‐ 2‐hydroxy‐1‐ PROPN eurjchem-32 60 29 naphthaldehyde naphthaldehyde NOUN eurjchem-32 60 30     SPACE eurjchem-32 60 31 ( ( PUNCT eurjchem-32 60 32 1.72 1.72 NUM eurjchem-32 60 33     SPACE eurjchem-32 60 34 g g NOUN eurjchem-32 60 35 , , PUNCT eurjchem-32 60 36     SPACE eurjchem-32 60 37 0.01 0.01 NUM eurjchem-32 60 38     SPACE eurjchem-32 60 39 mol mol NOUN eurjchem-32 60 40 ) ) PUNCT eurjchem-32 60 41     SPACE eurjchem-32 60 42 in in ADP eurjchem-32 60 43     SPACE eurjchem-32 60 44 ethanol ethanol NOUN eurjchem-32 60 45     SPACE eurjchem-32 60 46 ( ( PUNCT eurjchem-32 60 47 30 30 NUM eurjchem-32 60 48     SPACE eurjchem-32 60 49 ml ml NOUN eurjchem-32 60 50 ) ) PUNCT eurjchem-32 60 51     SPACE eurjchem-32 60 52 was be AUX eurjchem-32 60 53     SPACE eurjchem-32 60 54 refluxed refluxe VERB eurjchem-32 60 55     SPACE eurjchem-32 60 56 for for ADP eurjchem-32 60 57     SPACE eurjchem-32 60 58 1 1 NUM eurjchem-32 60 59     SPACE eurjchem-32 60 60 h h NOUN eurjchem-32 60 61     SPACE eurjchem-32 60 62 ( ( PUNCT eurjchem-32 60 63 scheme scheme NOUN eurjchem-32 60 64     SPACE eurjchem-32 60 65 9 9 NUM eurjchem-32 60 66 ) ) PUNCT eurjchem-32 60 67 . . PUNCT eurjchem-32 60 68     SPACE eurjchem-32 61 1 the the DET eurjchem-32 61 2     SPACE eurjchem-32 61 3 solid solid ADJ eurjchem-32 61 4     SPACE eurjchem-32 61 5 product product NOUN eurjchem-32 61 6     SPACE eurjchem-32 61 7 obtained obtain VERB eurjchem-32 61 8     SPACE eurjchem-32 61 9 was be AUX eurjchem-32 61 10     SPACE eurjchem-32 61 11 filtered filter VERB eurjchem-32 61 12     SPACE eurjchem-32 61 13 off off ADP eurjchem-32 61 14 , , PUNCT eurjchem-32 61 15     SPACE eurjchem-32 61 16 dried dry VERB eurjchem-32 61 17     SPACE eurjchem-32 61 18 and and CCONJ eurjchem-32 61 19     SPACE eurjchem-32 61 20 recrystallized recrystallize VERB eurjchem-32 61 21     SPACE eurjchem-32 61 22 from from ADP eurjchem-32 61 23     SPACE eurjchem-32 61 24 ethanol ethanol NOUN eurjchem-32 61 25     SPACE eurjchem-32 61 26 to to PART eurjchem-32 61 27     SPACE eurjchem-32 61 28 furnish furnish VERB eurjchem-32 61 29     SPACE eurjchem-32 61 30 3.08 3.08 NUM eurjchem-32 61 31     SPACE eurjchem-32 61 32 g g NOUN eurjchem-32 61 33     SPACE eurjchem-32 61 34 ( ( PUNCT eurjchem-32 61 35 78 78 NUM eurjchem-32 61 36 % % NOUN eurjchem-32 61 37 ) ) PUNCT eurjchem-32 61 38     SPACE eurjchem-32 61 39 of of ADP eurjchem-32 61 40     SPACE eurjchem-32 61 41 17 17 NUM eurjchem-32 61 42 ; ; PUNCT eurjchem-32 61 43     SPACE eurjchem-32 61 44 mp mp NOUN eurjchem-32 61 45     SPACE eurjchem-32 61 46 260 260 NUM eurjchem-32 61 47     SPACE eurjchem-32 61 48 oc oc NOUN eurjchem-32 61 49 ; ; PUNCT eurjchem-32 61 50     SPACE eurjchem-32 61 51 deep deep ADJ eurjchem-32 61 52     SPACE eurjchem-32 61 53 yellow yellow ADJ eurjchem-32 61 54     SPACE eurjchem-32 61 55 powder powder NOUN eurjchem-32 61 56 ; ; PUNCT eurjchem-32 61 57     SPACE eurjchem-32 61 58 ir ir VERB eurjchem-32 61 59     SPACE eurjchem-32 61 60 ( ( PUNCT eurjchem-32 61 61 kbr kbr PROPN eurjchem-32 61 62 ) ) PUNCT eurjchem-32 61 63     SPACE eurjchem-32 61 64 ( ( PUNCT eurjchem-32 61 65 υ υ INTJ eurjchem-32 61 66 , , PUNCT eurjchem-32 61 67     SPACE eurjchem-32 61 68 cm‐1 cm‐1 NOUN eurjchem-32 61 69 ): ): PUNCT eurjchem-32 61 70     SPACE eurjchem-32 61 71 3300‐3400 3300‐3400 NUM eurjchem-32 61 72     SPACE eurjchem-32 61 73 ( ( PUNCT eurjchem-32 61 74 nh2 nh2 PROPN eurjchem-32 61 75 ) ) PUNCT eurjchem-32 61 76 . . PUNCT eurjchem-32 61 77     SPACE eurjchem-32 62 1 1h 1h NUM eurjchem-32 62 2     SPACE eurjchem-32 62 3 nmr nmr NOUN eurjchem-32 62 4     SPACE eurjchem-32 62 5 ( ( PUNCT eurjchem-32 62 6 dmso‐d6 dmso‐d6 NOUN eurjchem-32 62 7 ): ): PUNCT eurjchem-32 62 8     SPACE eurjchem-32 62 9 δ δ PROPN eurjchem-32 62 10 , , PUNCT eurjchem-32 62 11     SPACE eurjchem-32 62 12 6.93 6.93 NUM eurjchem-32 62 13     SPACE eurjchem-32 62 14 ( ( PUNCT eurjchem-32 62 15 d d PROPN eurjchem-32 62 16 , , PUNCT eurjchem-32 62 17     SPACE eurjchem-32 62 18 1h 1h NUM eurjchem-32 62 19 , , PUNCT eurjchem-32 62 20     SPACE eurjchem-32 62 21 ch ch NOUN eurjchem-32 62 22 ) ) PUNCT eurjchem-32 62 23 , , PUNCT eurjchem-32 62 24     SPACE eurjchem-32 62 25 7.71 7.71 NUM eurjchem-32 62 26     SPACE eurjchem-32 62 27 ( ( PUNCT eurjchem-32 62 28 d d PROPN eurjchem-32 62 29 , , PUNCT eurjchem-32 62 30     SPACE eurjchem-32 62 31 1h 1h NUM eurjchem-32 62 32 , , PUNCT eurjchem-32 62 33     SPACE eurjchem-32 62 34 ch ch NOUN eurjchem-32 62 35 ) ) PUNCT eurjchem-32 62 36 , , PUNCT eurjchem-32 62 37     SPACE eurjchem-32 62 38 7.4‐8.19 7.4‐8.19 NOUN eurjchem-32 62 39     SPACE eurjchem-32 62 40 ( ( PUNCT eurjchem-32 62 41 m m PROPN eurjchem-32 62 42 , , PUNCT eurjchem-32 62 43     SPACE eurjchem-32 62 44 8h 8h NUM eurjchem-32 62 45 , , PUNCT eurjchem-32 62 46     SPACE eurjchem-32 62 47 ar‐h ar‐h NOUN eurjchem-32 62 48 ) ) PUNCT eurjchem-32 62 49 , , PUNCT eurjchem-32 62 50     SPACE eurjchem-32 62 51 8.6 8.6 NUM eurjchem-32 62 52     SPACE eurjchem-32 62 53 ( ( PUNCT eurjchem-32 62 54 s s PROPN eurjchem-32 62 55 , , PUNCT eurjchem-32 62 56     SPACE eurjchem-32 62 57 2h 2h NUM eurjchem-32 62 58 , , PUNCT eurjchem-32 62 59     SPACE eurjchem-32 62 60 nh2 nh2 PROPN eurjchem-32 62 61 ) ) PUNCT eurjchem-32 62 62 , , PUNCT eurjchem-32 62 63     SPACE eurjchem-32 62 64 8.77 8.77 NUM eurjchem-32 62 65     SPACE eurjchem-32 62 66 ( ( PUNCT eurjchem-32 62 67 s s PROPN eurjchem-32 62 68 , , PUNCT eurjchem-32 62 69     SPACE eurjchem-32 62 70 1h 1h NUM eurjchem-32 62 71 , , PUNCT eurjchem-32 62 72     SPACE eurjchem-32 62 73 ch ch NOUN eurjchem-32 62 74 ) ) PUNCT eurjchem-32 62 75 . . PUNCT eurjchem-32 62 76     SPACE eurjchem-32 63 1 ms ms NOUN eurjchem-32 63 2 : : PUNCT eurjchem-32 63 3     SPACE eurjchem-32 63 4 ( ( PUNCT eurjchem-32 63 5 m m PROPN eurjchem-32 63 6 / / SYM eurjchem-32 63 7 z z NOUN eurjchem-32 63 8 , , PUNCT eurjchem-32 63 9     SPACE eurjchem-32 63 10 % % NOUN eurjchem-32 63 11 ): ): PUNCT eurjchem-32 63 12     SPACE eurjchem-32 63 13 395 395 NUM eurjchem-32 63 14     SPACE eurjchem-32 63 15 ( ( PUNCT eurjchem-32 63 16 m+ m+ NUM eurjchem-32 63 17 , , PUNCT eurjchem-32 63 18     SPACE eurjchem-32 63 19 92 92 NUM eurjchem-32 63 20 ) ) PUNCT eurjchem-32 63 21 , , PUNCT eurjchem-32 63 22     SPACE eurjchem-32 63 23 311 311 NUM eurjchem-32 63 24     SPACE eurjchem-32 63 25 ( ( PUNCT eurjchem-32 63 26 30.6 30.6 NUM eurjchem-32 63 27 ) ) PUNCT eurjchem-32 63 28 , , PUNCT eurjchem-32 63 29     SPACE eurjchem-32 63 30 222 222 NUM eurjchem-32 63 31     SPACE eurjchem-32 63 32 ( ( PUNCT eurjchem-32 63 33 18.7 18.7 NUM eurjchem-32 63 34 ) ) PUNCT eurjchem-32 63 35 , , PUNCT eurjchem-32 63 36     SPACE eurjchem-32 63 37 174 174 NUM eurjchem-32 63 38     SPACE eurjchem-32 63 39 ( ( PUNCT eurjchem-32 63 40 100.0 100.0 NUM eurjchem-32 63 41 ) ) PUNCT eurjchem-32 63 42 , , PUNCT eurjchem-32 63 43     SPACE eurjchem-32 63 44 69 69 NUM eurjchem-32 63 45     SPACE eurjchem-32 63 46 ( ( PUNCT eurjchem-32 63 47 69.4 69.4 NUM eurjchem-32 63 48 ) ) PUNCT eurjchem-32 63 49 . . PUNCT eurjchem-32 63 50     SPACE eurjchem-32 64 1 anal anal ADJ eurjchem-32 64 2 . . PUNCT eurjchem-32 64 3     SPACE eurjchem-32 64 4 calcd calcd NOUN eurjchem-32 64 5 . . PUNCT eurjchem-32 64 6     SPACE eurjchem-32 64 7 for for ADP eurjchem-32 64 8     SPACE eurjchem-32 64 9 c23h13n3o2s c23h13n3o2s PROPN eurjchem-32 64 10 : : PUNCT eurjchem-32 64 11     SPACE eurjchem-32 64 12 c c X eurjchem-32 64 13 , , PUNCT eurjchem-32 64 14     SPACE eurjchem-32 64 15 69.86 69.86 NUM eurjchem-32 64 16 ; ; PUNCT eurjchem-32 64 17     SPACE eurjchem-32 64 18 h h NOUN eurjchem-32 64 19 , , PUNCT eurjchem-32 64 20     SPACE eurjchem-32 64 21 3.31 3.31 NUM eurjchem-32 64 22 ; ; PUNCT eurjchem-32 64 23     SPACE eurjchem-32 64 24 n n CCONJ eurjchem-32 64 25 , , PUNCT eurjchem-32 64 26     SPACE eurjchem-32 64 27 10.63 10.63 NUM eurjchem-32 64 28 . . PUNCT eurjchem-32 64 29     SPACE eurjchem-32 64 30 found find VERB eurjchem-32 64 31 : : PUNCT eurjchem-32 64 32     SPACE eurjchem-32 64 33 c c X eurjchem-32 64 34 , , PUNCT eurjchem-32 64 35     SPACE eurjchem-32 64 36 69.94 69.94 NUM eurjchem-32 64 37 ; ; PUNCT eurjchem-32 64 38     SPACE eurjchem-32 64 39 h h NOUN eurjchem-32 64 40 , , PUNCT eurjchem-32 64 41     SPACE eurjchem-32 64 42 3.37 3.37 NUM eurjchem-32 64 43 ; ; PUNCT eurjchem-32 64 44     SPACE eurjchem-32 64 45 n n CCONJ eurjchem-32 64 46 , , PUNCT eurjchem-32 64 47     SPACE eurjchem-32 64 48 10.71 10.71 NUM eurjchem-32 64 49 . . PUNCT eurjchem-32 64 50         SPACE eurjchem-32 64 51 scheme scheme NOUN eurjchem-32 64 52     SPACE eurjchem-32 64 53 9 9 NUM eurjchem-32 64 54         SPACE eurjchem-32 64 55 2.9 2.9 NUM eurjchem-32 64 56 . . PUNCT eurjchem-32 64 57     SPACE eurjchem-32 65 1 2­(5­aminoisoxazol­3­yl)­2­(benzo[d]thiazol­2­yl)­ 2­(5­aminoisoxazol­3­yl)­2­(benzo[d]thiazol­2­yl)­ NUM eurjchem-32 65 2 acetonitrile acetonitrile NOUN eurjchem-32 65 3 , , PUNCT eurjchem-32 65 4     SPACE eurjchem-32 65 5 18 18 NUM eurjchem-32 65 6           SPACE eurjchem-32 65 7 a a DET eurjchem-32 65 8     SPACE eurjchem-32 65 9 mixture mixture NOUN eurjchem-32 65 10     SPACE eurjchem-32 65 11 of of ADP eurjchem-32 65 12     SPACE eurjchem-32 65 13 4 4 NUM eurjchem-32 65 14     SPACE eurjchem-32 65 15 ( ( PUNCT eurjchem-32 65 16 2.41 2.41 NUM eurjchem-32 65 17     SPACE eurjchem-32 65 18 g g NOUN eurjchem-32 65 19 , , PUNCT eurjchem-32 65 20     SPACE eurjchem-32 65 21 0.01 0.01 NUM eurjchem-32 65 22     SPACE eurjchem-32 65 23 mol mol NOUN eurjchem-32 65 24 ) ) PUNCT eurjchem-32 65 25     SPACE eurjchem-32 65 26 and and CCONJ eurjchem-32 65 27     SPACE eurjchem-32 65 28 hydroxylamine hydroxylamine NOUN eurjchem-32 65 29     SPACE eurjchem-32 65 30 hydrochloride hydrochloride NOUN eurjchem-32 65 31     SPACE eurjchem-32 65 32 ( ( PUNCT eurjchem-32 65 33 0.69 0.69 NUM eurjchem-32 65 34     SPACE eurjchem-32 65 35 g g NOUN eurjchem-32 65 36 , , PUNCT eurjchem-32 65 37     SPACE eurjchem-32 65 38 0.01 0.01 NUM eurjchem-32 65 39     SPACE eurjchem-32 65 40 mol mol NOUN eurjchem-32 65 41 ) ) PUNCT eurjchem-32 65 42     SPACE eurjchem-32 65 43 in in ADP eurjchem-32 65 44     SPACE eurjchem-32 65 45 dmf dmf PROPN eurjchem-32 65 46     SPACE eurjchem-32 65 47 ( ( PUNCT eurjchem-32 65 48 15 15 NUM eurjchem-32 65 49     SPACE eurjchem-32 65 50 ml ml NOUN eurjchem-32 65 51 ) ) PUNCT eurjchem-32 65 52     SPACE eurjchem-32 65 53 containing contain VERB eurjchem-32 65 54     SPACE eurjchem-32 65 55 a a DET eurjchem-32 65 56     SPACE eurjchem-32 65 57 catalytic catalytic ADJ eurjchem-32 65 58     SPACE eurjchem-32 65 59 amount amount NOUN eurjchem-32 65 60     SPACE eurjchem-32 65 61 of of ADP eurjchem-32 65 62     SPACE eurjchem-32 65 63 tea tea NOUN eurjchem-32 65 64     SPACE eurjchem-32 65 65 was be AUX eurjchem-32 65 66     SPACE eurjchem-32 65 67 refluxed refluxe VERB eurjchem-32 65 68     SPACE eurjchem-32 65 69 for for ADP eurjchem-32 65 70     SPACE eurjchem-32 65 71 6 6 NUM eurjchem-32 65 72     SPACE eurjchem-32 65 73 h h NOUN eurjchem-32 65 74     SPACE eurjchem-32 65 75 ( ( PUNCT eurjchem-32 65 76 scheme scheme NOUN eurjchem-32 65 77     SPACE eurjchem-32 65 78 10 10 NUM eurjchem-32 65 79 ) ) PUNCT eurjchem-32 65 80 . . PUNCT eurjchem-32 65 81     SPACE eurjchem-32 66 1 the the DET eurjchem-32 66 2     SPACE eurjchem-32 66 3 reaction reaction NOUN eurjchem-32 66 4     SPACE eurjchem-32 66 5 mixture mixture NOUN eurjchem-32 66 6     SPACE eurjchem-32 66 7 was be AUX eurjchem-32 66 8     SPACE eurjchem-32 66 9 left leave VERB eurjchem-32 66 10     SPACE eurjchem-32 66 11 to to PART eurjchem-32 66 12     SPACE eurjchem-32 66 13 cool cool VERB eurjchem-32 66 14     SPACE eurjchem-32 66 15 and and CCONJ eurjchem-32 66 16     SPACE eurjchem-32 66 17 poured pour VERB eurjchem-32 66 18     SPACE eurjchem-32 66 19 into into ADP eurjchem-32 66 20     SPACE eurjchem-32 66 21 ice ice NOUN eurjchem-32 66 22     SPACE eurjchem-32 66 23 cold cold ADJ eurjchem-32 66 24     SPACE eurjchem-32 66 25 water water NOUN eurjchem-32 66 26 . . PUNCT eurjchem-32 66 27     SPACE eurjchem-32 67 1 the the DET eurjchem-32 67 2     SPACE eurjchem-32 67 3 precipitated precipitate VERB eurjchem-32 67 4     SPACE eurjchem-32 67 5 solid solid ADJ eurjchem-32 67 6     SPACE eurjchem-32 67 7 was be AUX eurjchem-32 67 8     SPACE eurjchem-32 67 9 filtered filter VERB eurjchem-32 67 10     SPACE eurjchem-32 67 11 off off ADP eurjchem-32 67 12 , , PUNCT eurjchem-32 67 13     SPACE eurjchem-32 67 14 dried dry VERB eurjchem-32 67 15     SPACE eurjchem-32 67 16 and and CCONJ eurjchem-32 67 17     SPACE eurjchem-32 67 18 recrystallized recrystallize VERB eurjchem-32 67 19     SPACE eurjchem-32 67 20 from from ADP eurjchem-32 67 21     SPACE eurjchem-32 67 22 ethanol ethanol NOUN eurjchem-32 67 23     SPACE eurjchem-32 67 24 to to PART eurjchem-32 67 25     SPACE eurjchem-32 67 26 afford afford VERB eurjchem-32 67 27     SPACE eurjchem-32 67 28 1.87 1.87 NUM eurjchem-32 67 29     SPACE eurjchem-32 67 30 g g NOUN eurjchem-32 67 31     SPACE eurjchem-32 67 32 ( ( PUNCT eurjchem-32 67 33 73 73 NUM eurjchem-32 67 34 % % NOUN eurjchem-32 67 35 ) ) PUNCT eurjchem-32 67 36     SPACE eurjchem-32 67 37 of of ADP eurjchem-32 67 38     SPACE eurjchem-32 67 39 18 18 NUM eurjchem-32 67 40 ; ; PUNCT eurjchem-32 67 41     SPACE eurjchem-32 67 42 mp mp NOUN eurjchem-32 67 43     SPACE eurjchem-32 67 44 160 160 NUM eurjchem-32 67 45     SPACE eurjchem-32 67 46 oc oc NOUN eurjchem-32 67 47 ; ; PUNCT eurjchem-32 67 48     SPACE eurjchem-32 67 49 brown brown ADJ eurjchem-32 67 50     SPACE eurjchem-32 67 51 powder powder NOUN eurjchem-32 67 52 ; ; PUNCT eurjchem-32 67 53     SPACE eurjchem-32 67 54 ir ir PROPN eurjchem-32 67 55     SPACE eurjchem-32 67 56 ( ( PUNCT eurjchem-32 67 57 kbr kbr PROPN eurjchem-32 67 58 ) ) PUNCT eurjchem-32 67 59     SPACE eurjchem-32 67 60 ( ( PUNCT eurjchem-32 67 61 υ υ NOUN eurjchem-32 67 62 , , PUNCT eurjchem-32 67 63     SPACE eurjchem-32 67 64 cm‐1 cm‐1 NOUN eurjchem-32 67 65 ): ): PUNCT eurjchem-32 67 66     SPACE eurjchem-32 67 67 3325 3325 NUM eurjchem-32 67 68 , , PUNCT eurjchem-32 67 69     SPACE eurjchem-32 67 70 3309 3309 NUM eurjchem-32 67 71     SPACE eurjchem-32 67 72 ( ( PUNCT eurjchem-32 67 73 nh2 nh2 PROPN eurjchem-32 67 74 ) ) PUNCT eurjchem-32 67 75 , , PUNCT eurjchem-32 67 76     SPACE eurjchem-32 67 77 2199 2199 NUM eurjchem-32 67 78     SPACE eurjchem-32 67 79 ( ( PUNCT eurjchem-32 67 80 cn cn PROPN eurjchem-32 67 81 ) ) PUNCT eurjchem-32 67 82 . . PUNCT eurjchem-32 67 83     SPACE eurjchem-32 67 84 1h 1h NUM eurjchem-32 67 85     SPACE eurjchem-32 67 86 nmr nmr NOUN eurjchem-32 67 87     SPACE eurjchem-32 67 88 ( ( PUNCT eurjchem-32 67 89 dmso‐d6 dmso‐d6 NOUN eurjchem-32 67 90 ): ): PUNCT eurjchem-32 67 91     SPACE eurjchem-32 67 92 δ δ PROPN eurjchem-32 67 93 , , PUNCT eurjchem-32 67 94     SPACE eurjchem-32 67 95 4.25 4.25 NUM eurjchem-32 67 96     SPACE eurjchem-32 67 97 ( ( PUNCT eurjchem-32 67 98 s s PROPN eurjchem-32 67 99 , , PUNCT eurjchem-32 67 100     SPACE eurjchem-32 67 101 1h 1h NUM eurjchem-32 67 102 , , PUNCT eurjchem-32 67 103     SPACE eurjchem-32 67 104 ch ch NOUN eurjchem-32 67 105 ) ) PUNCT eurjchem-32 67 106 , , PUNCT eurjchem-32 67 107     SPACE eurjchem-32 67 108 7.2 7.2 NUM eurjchem-32 67 109     SPACE eurjchem-32 67 110 ( ( PUNCT eurjchem-32 67 111 s s PROPN eurjchem-32 67 112 , , PUNCT eurjchem-32 67 113     SPACE eurjchem-32 67 114 1h 1h NUM eurjchem-32 67 115 , , PUNCT eurjchem-32 67 116     SPACE eurjchem-32 67 117 ch ch NOUN eurjchem-32 67 118 ) ) PUNCT eurjchem-32 67 119 , , PUNCT eurjchem-32 67 120     SPACE eurjchem-32 67 121 7.3‐8.1 7.3‐8.1 NUM eurjchem-32 67 122     SPACE eurjchem-32 67 123 ( ( PUNCT eurjchem-32 67 124 m m PROPN eurjchem-32 67 125 , , PUNCT eurjchem-32 67 126     SPACE eurjchem-32 67 127 4h 4h NOUN eurjchem-32 67 128 , , PUNCT eurjchem-32 67 129     SPACE eurjchem-32 67 130 ar‐h ar‐h NOUN eurjchem-32 67 131 ) ) PUNCT eurjchem-32 67 132 , , PUNCT eurjchem-32 67 133     SPACE eurjchem-32 67 134 8.19 8.19 NUM eurjchem-32 67 135     SPACE eurjchem-32 67 136 ( ( PUNCT eurjchem-32 67 137 s s PROPN eurjchem-32 67 138 , , PUNCT eurjchem-32 67 139     SPACE eurjchem-32 67 140 2h 2h NUM eurjchem-32 67 141 , , PUNCT eurjchem-32 67 142     SPACE eurjchem-32 67 143 nh2 nh2 PROPN eurjchem-32 67 144 ) ) PUNCT eurjchem-32 67 145 . . PUNCT eurjchem-32 67 146     SPACE eurjchem-32 67 147 13c 13c NOUN eurjchem-32 67 148     SPACE eurjchem-32 67 149 nmr nmr NOUN eurjchem-32 67 150     SPACE eurjchem-32 67 151 ( ( PUNCT eurjchem-32 67 152 dmso‐ dmso‐ PROPN eurjchem-32 67 153 d6 d6 NOUN eurjchem-32 67 154 ): ): PUNCT eurjchem-32 67 155     SPACE eurjchem-32 67 156 δ δ PROPN eurjchem-32 67 157 , , PUNCT eurjchem-32 67 158     SPACE eurjchem-32 67 159 179.75 179.75 NUM eurjchem-32 67 160 , , PUNCT eurjchem-32 67 161     SPACE eurjchem-32 67 162 166.75 166.75 NUM eurjchem-32 67 163 , , PUNCT eurjchem-32 67 164     SPACE eurjchem-32 67 165 150.04 150.04 NUM eurjchem-32 67 166 , , PUNCT eurjchem-32 67 167     SPACE eurjchem-32 67 168 139.35 139.35 NUM eurjchem-32 67 169 , , PUNCT eurjchem-32 67 170     SPACE eurjchem-32 67 171 127.58 127.58 NUM eurjchem-32 67 172 , , PUNCT eurjchem-32 67 173     SPACE eurjchem-32 67 174 127.19 127.19 NUM eurjchem-32 67 175 , , PUNCT eurjchem-32 67 176     SPACE eurjchem-32 67 177 124.33 124.33 NUM eurjchem-32 67 178 , , PUNCT eurjchem-32 67 179     SPACE eurjchem-32 67 180 122.74 122.74 NUM eurjchem-32 67 181 , , PUNCT eurjchem-32 67 182     SPACE eurjchem-32 67 183 118.08 118.08 NUM eurjchem-32 67 184 , , PUNCT eurjchem-32 67 185     SPACE eurjchem-32 67 186 115.99 115.99 NUM eurjchem-32 67 187 , , PUNCT eurjchem-32 67 188     SPACE eurjchem-32 67 189 114.66 114.66 NUM eurjchem-32 67 190 , , PUNCT eurjchem-32 67 191     SPACE eurjchem-32 67 192 75.52 75.52 NUM eurjchem-32 67 193 , , PUNCT eurjchem-32 67 194     SPACE eurjchem-32 67 195 40.40 40.40 NUM eurjchem-32 67 196 , , PUNCT eurjchem-32 67 197     SPACE eurjchem-32 67 198 40.12 40.12 NUM eurjchem-32 67 199 , , PUNCT eurjchem-32 67 200     SPACE eurjchem-32 67 201 39.84 39.84 NUM eurjchem-32 67 202 , , PUNCT eurjchem-32 67 203     SPACE eurjchem-32 67 204 39.56 39.56 NUM eurjchem-32 67 205 , , PUNCT eurjchem-32 67 206     SPACE eurjchem-32 67 207 39.28 39.28 NUM eurjchem-32 67 208 , , PUNCT eurjchem-32 67 209     SPACE eurjchem-32 67 210 39.01 39.01 NUM eurjchem-32 67 211 , , PUNCT eurjchem-32 67 212     SPACE eurjchem-32 67 213 38.73 38.73 NUM eurjchem-32 67 214 . . PUNCT eurjchem-32 67 215     SPACE eurjchem-32 68 1 ms ms NOUN eurjchem-32 68 2 : : PUNCT eurjchem-32 68 3     SPACE eurjchem-32 68 4 ( ( PUNCT eurjchem-32 68 5 m m PROPN eurjchem-32 68 6 / / SYM eurjchem-32 68 7 z z NOUN eurjchem-32 68 8 , , PUNCT eurjchem-32 68 9     SPACE eurjchem-32 68 10 % % NOUN eurjchem-32 68 11 ): ): PUNCT eurjchem-32 68 12     SPACE eurjchem-32 68 13 258 258 NUM eurjchem-32 68 14     SPACE eurjchem-32 68 15 ( ( PUNCT eurjchem-32 68 16 m++2 m++2 PROPN eurjchem-32 68 17 , , PUNCT eurjchem-32 68 18     SPACE eurjchem-32 68 19 11.8 11.8 NUM eurjchem-32 68 20 ) ) PUNCT eurjchem-32 68 21 , , PUNCT eurjchem-32 68 22     SPACE eurjchem-32 68 23 201 201 NUM eurjchem-32 68 24     SPACE eurjchem-32 68 25 ( ( PUNCT eurjchem-32 68 26 73.7 73.7 NUM eurjchem-32 68 27 ) ) PUNCT eurjchem-32 68 28 , , PUNCT eurjchem-32 68 29     SPACE eurjchem-32 68 30 174 174 NUM eurjchem-32 68 31     SPACE eurjchem-32 68 32 ( ( PUNCT eurjchem-32 68 33 100.0 100.0 NUM eurjchem-32 68 34 ) ) PUNCT eurjchem-32 68 35 , , PUNCT eurjchem-32 68 36     SPACE eurjchem-32 68 37 146 146 NUM eurjchem-32 68 38     SPACE eurjchem-32 68 39 ( ( PUNCT eurjchem-32 68 40 44.7 44.7 NUM eurjchem-32 68 41 ) ) PUNCT eurjchem-32 68 42 , , PUNCT eurjchem-32 68 43     SPACE eurjchem-32 68 44 108 108 NUM eurjchem-32 68 45     SPACE eurjchem-32 68 46 ( ( PUNCT eurjchem-32 68 47 36.8 36.8 NUM eurjchem-32 68 48 ) ) PUNCT eurjchem-32 68 49 , , PUNCT eurjchem-32 68 50     SPACE eurjchem-32 68 51 69 69 NUM eurjchem-32 68 52     SPACE eurjchem-32 68 53 ( ( PUNCT eurjchem-32 68 54 89.5 89.5 NUM eurjchem-32 68 55 ) ) PUNCT eurjchem-32 68 56 . . PUNCT eurjchem-32 68 57     SPACE eurjchem-32 69 1 anal anal ADJ eurjchem-32 69 2 . . PUNCT eurjchem-32 69 3     SPACE eurjchem-32 69 4 calcd calcd NOUN eurjchem-32 69 5 . . PUNCT eurjchem-32 69 6     SPACE eurjchem-32 69 7 for for ADP eurjchem-32 69 8     SPACE eurjchem-32 69 9 c12h8n4os c12h8n4os PROPN eurjchem-32 69 10 : : PUNCT eurjchem-32 69 11     SPACE eurjchem-32 69 12 c c X eurjchem-32 69 13 , , PUNCT eurjchem-32 69 14     SPACE eurjchem-32 69 15 56.24 56.24 NUM eurjchem-32 69 16 ; ; PUNCT eurjchem-32 69 17     SPACE eurjchem-32 69 18 h h NOUN eurjchem-32 69 19 , , PUNCT eurjchem-32 69 20     SPACE eurjchem-32 69 21 3.15 3.15 NUM eurjchem-32 69 22 ; ; PUNCT eurjchem-32 69 23     SPACE eurjchem-32 69 24 n n CCONJ eurjchem-32 69 25 , , PUNCT eurjchem-32 69 26     SPACE eurjchem-32 69 27 21.86 21.86 NUM eurjchem-32 69 28 . . PUNCT eurjchem-32 69 29     SPACE eurjchem-32 69 30 found find VERB eurjchem-32 69 31 : : PUNCT eurjchem-32 69 32     SPACE eurjchem-32 69 33 c c X eurjchem-32 69 34 , , PUNCT eurjchem-32 69 35     SPACE eurjchem-32 69 36 56.19 56.19 NUM eurjchem-32 69 37 ; ; PUNCT eurjchem-32 69 38     SPACE eurjchem-32 69 39 h h NOUN eurjchem-32 69 40 , , PUNCT eurjchem-32 69 41     SPACE eurjchem-32 69 42 3.11 3.11 NUM eurjchem-32 69 43 ; ; PUNCT eurjchem-32 69 44     SPACE eurjchem-32 69 45 n n CCONJ eurjchem-32 69 46 , , PUNCT eurjchem-32 69 47     SPACE eurjchem-32 69 48 21.83 21.83 NUM eurjchem-32 69 49 . . PUNCT eurjchem-32 69 50     SPACE eurjchem-32 69 51 scheme scheme NOUN eurjchem-32 69 52     SPACE eurjchem-32 69 53 10 10 NUM eurjchem-32 69 54         SPACE eurjchem-32 69 55 2.10 2.10 NUM eurjchem-32 69 56 . . PUNCT eurjchem-32 69 57     SPACE eurjchem-32 70 1 3,7­diamino­4­(benzo[d]thiazol­2­yl)­4h­1,2­diazepin­ 3,7­diamino­4­(benzo[d]thiazol­2­yl)­4h­1,2­diazepin­ NUM eurjchem-32 70 2 5(6h)­one 5(6h)­one NOUN eurjchem-32 70 3 , , PUNCT eurjchem-32 70 4     SPACE eurjchem-32 70 5 19 19 NUM eurjchem-32 70 6           SPACE eurjchem-32 70 7 to to ADP eurjchem-32 70 8     SPACE eurjchem-32 70 9 a a DET eurjchem-32 70 10     SPACE eurjchem-32 70 11 mixture mixture NOUN eurjchem-32 70 12     SPACE eurjchem-32 70 13 of of ADP eurjchem-32 70 14     SPACE eurjchem-32 70 15 4 4 NUM eurjchem-32 70 16     SPACE eurjchem-32 70 17 ( ( PUNCT eurjchem-32 70 18 2.41 2.41 NUM eurjchem-32 70 19     SPACE eurjchem-32 70 20 g g NOUN eurjchem-32 70 21 , , PUNCT eurjchem-32 70 22     SPACE eurjchem-32 70 23 0.01 0.01 NUM eurjchem-32 70 24     SPACE eurjchem-32 70 25 mol mol NOUN eurjchem-32 70 26 ) ) PUNCT eurjchem-32 70 27     SPACE eurjchem-32 70 28 and and CCONJ eurjchem-32 70 29     SPACE eurjchem-32 70 30 hydrazine hydrazine NOUN eurjchem-32 70 31     SPACE eurjchem-32 70 32 hydrate hydrate NOUN eurjchem-32 70 33     SPACE eurjchem-32 70 34 ( ( PUNCT eurjchem-32 70 35 0.75 0.75 NUM eurjchem-32 70 36     SPACE eurjchem-32 70 37 g g NOUN eurjchem-32 70 38 , , PUNCT eurjchem-32 70 39     SPACE eurjchem-32 70 40 0.015 0.015 NUM eurjchem-32 70 41     SPACE eurjchem-32 70 42 mol mol NOUN eurjchem-32 70 43 ) ) PUNCT eurjchem-32 70 44     SPACE eurjchem-32 70 45 in in ADP eurjchem-32 70 46     SPACE eurjchem-32 70 47 ethanol ethanol NOUN eurjchem-32 70 48     SPACE eurjchem-32 70 49 ( ( PUNCT eurjchem-32 70 50 15 15 NUM eurjchem-32 70 51     SPACE eurjchem-32 70 52 ml ml NOUN eurjchem-32 70 53 ) ) PUNCT eurjchem-32 70 54 , , PUNCT eurjchem-32 70 55     SPACE eurjchem-32 70 56 freshly freshly ADV eurjchem-32 70 57     SPACE eurjchem-32 70 58 fused fuse VERB eurjchem-32 70 59     SPACE eurjchem-32 70 60 sodium sodium NOUN eurjchem-32 70 61     SPACE eurjchem-32 70 62 acetate acetate NOUN eurjchem-32 70 63     SPACE eurjchem-32 70 64 ( ( PUNCT eurjchem-32 70 65 1.23 1.23 NUM eurjchem-32 70 66     SPACE eurjchem-32 70 67 g g NOUN eurjchem-32 70 68 , , PUNCT eurjchem-32 70 69     SPACE eurjchem-32 70 70 0.015 0.015 NUM eurjchem-32 70 71     SPACE eurjchem-32 70 72 mol mol NOUN eurjchem-32 70 73 ) ) PUNCT eurjchem-32 70 74     SPACE eurjchem-32 70 75 was be AUX eurjchem-32 70 76     SPACE eurjchem-32 70 77 added add VERB eurjchem-32 70 78     SPACE eurjchem-32 70 79 ( ( PUNCT eurjchem-32 70 80 scheme scheme NOUN eurjchem-32 70 81     SPACE eurjchem-32 70 82 10 10 NUM eurjchem-32 70 83 ) ) PUNCT eurjchem-32 70 84 . . PUNCT eurjchem-32 70 85     SPACE eurjchem-32 71 1 the the DET eurjchem-32 71 2     SPACE eurjchem-32 71 3 reaction reaction NOUN eurjchem-32 71 4     SPACE eurjchem-32 71 5 mixture mixture NOUN eurjchem-32 71 6     SPACE eurjchem-32 71 7 was be AUX eurjchem-32 71 8     SPACE eurjchem-32 71 9 refluxed refluxe VERB eurjchem-32 71 10     SPACE eurjchem-32 71 11 for for ADP eurjchem-32 71 12     SPACE eurjchem-32 71 13 4 4 NUM eurjchem-32 71 14     SPACE eurjchem-32 71 15 h h NOUN eurjchem-32 71 16 , , PUNCT eurjchem-32 71 17     SPACE eurjchem-32 71 18 allow allow VERB eurjchem-32 71 19     SPACE eurjchem-32 71 20 to to PART eurjchem-32 71 21     SPACE eurjchem-32 71 22 cool cool VERB eurjchem-32 71 23     SPACE eurjchem-32 71 24 at at ADP eurjchem-32 71 25     SPACE eurjchem-32 71 26 room room NOUN eurjchem-32 71 27     SPACE eurjchem-32 71 28 temperature temperature NOUN eurjchem-32 71 29 . . PUNCT eurjchem-32 71 30     SPACE eurjchem-32 72 1 the the DET eurjchem-32 72 2     SPACE eurjchem-32 72 3 reaction reaction NOUN eurjchem-32 72 4     SPACE eurjchem-32 72 5 mixture mixture NOUN eurjchem-32 72 6     SPACE eurjchem-32 72 7 was be AUX eurjchem-32 72 8     SPACE eurjchem-32 72 9 poured pour VERB eurjchem-32 72 10     SPACE eurjchem-32 72 11 into into ADP eurjchem-32 72 12     SPACE eurjchem-32 72 13 ice ice NOUN eurjchem-32 72 14     SPACE eurjchem-32 72 15 cold cold ADJ eurjchem-32 72 16     SPACE eurjchem-32 72 17 water water NOUN eurjchem-32 72 18 , , PUNCT eurjchem-32 72 19     SPACE eurjchem-32 72 20 the the DET eurjchem-32 72 21     SPACE eurjchem-32 72 22 solid solid NOUN eurjchem-32 72 23     SPACE eurjchem-32 72 24 formed form VERB eurjchem-32 72 25     SPACE eurjchem-32 72 26 was be AUX eurjchem-32 72 27     SPACE eurjchem-32 72 28 filtered filter VERB eurjchem-32 72 29     SPACE eurjchem-32 72 30 off off ADP eurjchem-32 72 31 , , PUNCT eurjchem-32 72 32     SPACE eurjchem-32 72 33 dried dry VERB eurjchem-32 72 34     SPACE eurjchem-32 72 35 and and CCONJ eurjchem-32 72 36     SPACE eurjchem-32 72 37 recrystallized recrystallize VERB eurjchem-32 72 38     SPACE eurjchem-32 72 39 from from ADP eurjchem-32 72 40     SPACE eurjchem-32 72 41 ethanol ethanol NOUN eurjchem-32 72 42     SPACE eurjchem-32 72 43 to to PART eurjchem-32 72 44     SPACE eurjchem-32 72 45 afford afford VERB eurjchem-32 72 46     SPACE eurjchem-32 72 47 2.08 2.08 NUM eurjchem-32 72 48     SPACE eurjchem-32 72 49 g g NOUN eurjchem-32 72 50     SPACE eurjchem-32 72 51 ( ( PUNCT eurjchem-32 72 52 76 76 NUM eurjchem-32 72 53 % % NOUN eurjchem-32 72 54 ) ) PUNCT eurjchem-32 72 55     SPACE eurjchem-32 72 56 of of ADP eurjchem-32 72 57     SPACE eurjchem-32 72 58 19 19 NUM eurjchem-32 72 59 ; ; PUNCT eurjchem-32 72 60     SPACE eurjchem-32 72 61 mp mp NOUN eurjchem-32 72 62     SPACE eurjchem-32 72 63 > > NOUN eurjchem-32 72 64     SPACE eurjchem-32 72 65 300 300 NUM eurjchem-32 72 66     SPACE eurjchem-32 72 67 oc oc NOUN eurjchem-32 72 68 ; ; PUNCT eurjchem-32 72 69     SPACE eurjchem-32 72 70 off off ADP eurjchem-32 72 71     SPACE eurjchem-32 72 72 white white ADJ eurjchem-32 72 73     SPACE eurjchem-32 72 74 powder powder NOUN eurjchem-32 72 75 ; ; PUNCT eurjchem-32 72 76     SPACE eurjchem-32 72 77 ir ir PROPN eurjchem-32 72 78     SPACE eurjchem-32 72 79 ( ( PUNCT eurjchem-32 72 80 kbr kbr PROPN eurjchem-32 72 81 ) ) PUNCT eurjchem-32 72 82     SPACE eurjchem-32 72 83 ( ( PUNCT eurjchem-32 72 84 υ υ NOUN eurjchem-32 72 85 , , PUNCT eurjchem-32 72 86     SPACE eurjchem-32 72 87 cm‐1 cm‐1 NOUN eurjchem-32 72 88 ): ): PUNCT eurjchem-32 72 89         SPACE eurjchem-32 72 90 3314 3314 NUM eurjchem-32 72 91 , , PUNCT eurjchem-32 72 92     SPACE eurjchem-32 72 93 3173 3173 NUM eurjchem-32 72 94     SPACE eurjchem-32 72 95 nh2 nh2 PROPN eurjchem-32 72 96 . . PUNCT eurjchem-32 72 97     SPACE eurjchem-32 72 98 1h 1h NUM eurjchem-32 72 99     SPACE eurjchem-32 72 100 nmr nmr NOUN eurjchem-32 72 101     SPACE eurjchem-32 72 102 ( ( PUNCT eurjchem-32 72 103 dmso‐d6 dmso‐d6 NOUN eurjchem-32 72 104 ): ): PUNCT eurjchem-32 72 105     SPACE eurjchem-32 72 106 δ δ PROPN eurjchem-32 72 107 , , PUNCT eurjchem-32 72 108     SPACE eurjchem-32 72 109 2.4:2.5 2.4:2.5 NUM eurjchem-32 72 110     SPACE eurjchem-32 72 111 ( ( PUNCT eurjchem-32 72 112 d.d d.d PROPN eurjchem-32 72 113 , , PUNCT eurjchem-32 72 114     SPACE eurjchem-32 72 115 2h 2h NUM eurjchem-32 72 116 , , PUNCT eurjchem-32 72 117     SPACE eurjchem-32 72 118 ch2 ch2 NOUN eurjchem-32 72 119 ) ) PUNCT eurjchem-32 72 120 , , PUNCT eurjchem-32 72 121     SPACE eurjchem-32 72 122 3.76 3.76 NUM eurjchem-32 72 123     SPACE eurjchem-32 72 124 ( ( PUNCT eurjchem-32 72 125 s s PROPN eurjchem-32 72 126 , , PUNCT eurjchem-32 72 127     SPACE eurjchem-32 72 128 1h 1h NUM eurjchem-32 72 129 , , PUNCT eurjchem-32 72 130     SPACE eurjchem-32 72 131 ch ch NOUN eurjchem-32 72 132 ) ) PUNCT eurjchem-32 72 133 , , PUNCT eurjchem-32 72 134     SPACE eurjchem-32 72 135 7.26‐8.12 7.26‐8.12 NUM eurjchem-32 72 136     SPACE eurjchem-32 72 137 fadda fadda NOUN eurjchem-32 72 138     SPACE eurjchem-32 72 139 et et PROPN eurjchem-32 72 140     SPACE eurjchem-32 72 141 al al PROPN eurjchem-32 72 142 . . PROPN eurjchem-32 72 143     SPACE eurjchem-32 72 144 / / SYM eurjchem-32 72 145     SPACE eurjchem-32 72 146 european european ADJ eurjchem-32 72 147     SPACE eurjchem-32 72 148 journal journal NOUN eurjchem-32 72 149     SPACE eurjchem-32 72 150 of of ADP eurjchem-32 72 151     SPACE eurjchem-32 72 152 chemistry chemistry NOUN eurjchem-32 72 153     SPACE eurjchem-32 72 154 1 1 NUM eurjchem-32 72 155     SPACE eurjchem-32 72 156 ( ( PUNCT eurjchem-32 72 157 2 2 NUM eurjchem-32 72 158 ) ) PUNCT eurjchem-32 72 159     SPACE eurjchem-32 72 160 ( ( PUNCT eurjchem-32 72 161 2010 2010 NUM eurjchem-32 72 162 ) ) PUNCT eurjchem-32 72 163     SPACE eurjchem-32 72 164 90­95 90­95 NUM eurjchem-32 72 165     SPACE eurjchem-32 72 166 93 93 NUM eurjchem-32 72 167     SPACE eurjchem-32 72 168 ( ( PUNCT eurjchem-32 72 169 m m PROPN eurjchem-32 72 170 , , PUNCT eurjchem-32 72 171     SPACE eurjchem-32 72 172 4h 4h NOUN eurjchem-32 72 173 , , PUNCT eurjchem-32 72 174     SPACE eurjchem-32 72 175 ar‐h ar‐h PROPN eurjchem-32 72 176 , , PUNCT eurjchem-32 72 177     SPACE eurjchem-32 72 178 2nh2 2nh2 NUM eurjchem-32 72 179 ) ) PUNCT eurjchem-32 72 180 , , PUNCT eurjchem-32 72 181     SPACE eurjchem-32 72 182 8.51 8.51 NUM eurjchem-32 72 183     SPACE eurjchem-32 72 184 ( ( PUNCT eurjchem-32 72 185 s s PROPN eurjchem-32 72 186 , , PUNCT eurjchem-32 72 187     SPACE eurjchem-32 72 188 4h 4h NOUN eurjchem-32 72 189 , , PUNCT eurjchem-32 72 190     SPACE eurjchem-32 72 191 2nh2 2nh2 NUM eurjchem-32 72 192 ) ) PUNCT eurjchem-32 72 193 . . PUNCT eurjchem-32 72 194     SPACE eurjchem-32 73 1 ms ms NOUN eurjchem-32 73 2 : : PUNCT eurjchem-32 73 3     SPACE eurjchem-32 73 4 ( ( PUNCT eurjchem-32 73 5 m m PROPN eurjchem-32 73 6 / / SYM eurjchem-32 73 7 z z NOUN eurjchem-32 73 8 , , PUNCT eurjchem-32 73 9     SPACE eurjchem-32 73 10 % % NOUN eurjchem-32 73 11 ): ): PUNCT eurjchem-32 73 12     SPACE eurjchem-32 73 13 275 275 NUM eurjchem-32 73 14     SPACE eurjchem-32 73 15 ( ( PUNCT eurjchem-32 73 16 m+ m+ NOUN eurjchem-32 73 17     SPACE eurjchem-32 73 18 +2 +2 NOUN eurjchem-32 73 19 , , PUNCT eurjchem-32 73 20     SPACE eurjchem-32 73 21 100.0 100.0 NUM eurjchem-32 73 22 ) ) PUNCT eurjchem-32 73 23 , , PUNCT eurjchem-32 73 24     SPACE eurjchem-32 73 25 273 273 NUM eurjchem-32 73 26     SPACE eurjchem-32 73 27 ( ( PUNCT eurjchem-32 73 28 m+ m+ NUM eurjchem-32 73 29 , , PUNCT eurjchem-32 73 30     SPACE eurjchem-32 73 31 12.8 12.8 NUM eurjchem-32 73 32 ) ) PUNCT eurjchem-32 73 33 , , PUNCT eurjchem-32 73 34     SPACE eurjchem-32 73 35 176 176 NUM eurjchem-32 73 36     SPACE eurjchem-32 73 37 ( ( PUNCT eurjchem-32 73 38 23.1 23.1 NUM eurjchem-32 73 39 ) ) PUNCT eurjchem-32 73 40 , , PUNCT eurjchem-32 73 41     SPACE eurjchem-32 73 42 123 123 NUM eurjchem-32 73 43     SPACE eurjchem-32 73 44 ( ( PUNCT eurjchem-32 73 45 14.1 14.1 NUM eurjchem-32 73 46 ) ) PUNCT eurjchem-32 73 47 , , PUNCT eurjchem-32 73 48     SPACE eurjchem-32 73 49 76 76 NUM eurjchem-32 73 50     SPACE eurjchem-32 73 51 ( ( PUNCT eurjchem-32 73 52 55.1 55.1 NUM eurjchem-32 73 53 ) ) PUNCT eurjchem-32 73 54 . . PUNCT eurjchem-32 73 55     SPACE eurjchem-32 74 1 anal anal ADJ eurjchem-32 74 2 . . PUNCT eurjchem-32 74 3     SPACE eurjchem-32 74 4 calcd calcd NOUN eurjchem-32 74 5 . . PUNCT eurjchem-32 74 6     SPACE eurjchem-32 74 7 for for ADP eurjchem-32 74 8     SPACE eurjchem-32 74 9 c12h11n5os c12h11n5o NOUN eurjchem-32 74 10 : : PUNCT eurjchem-32 74 11     SPACE eurjchem-32 74 12 c c X eurjchem-32 74 13 , , PUNCT eurjchem-32 74 14     SPACE eurjchem-32 74 15 52.73 52.73 NUM eurjchem-32 74 16 ; ; PUNCT eurjchem-32 74 17     SPACE eurjchem-32 74 18 h h NOUN eurjchem-32 74 19 , , PUNCT eurjchem-32 74 20     SPACE eurjchem-32 74 21 4.06 4.06 NUM eurjchem-32 74 22 ; ; PUNCT eurjchem-32 74 23     SPACE eurjchem-32 74 24 n n CCONJ eurjchem-32 74 25 , , PUNCT eurjchem-32 74 26     SPACE eurjchem-32 74 27 25.62 25.62 NUM eurjchem-32 74 28 . . PUNCT eurjchem-32 74 29     SPACE eurjchem-32 74 30 found find VERB eurjchem-32 74 31 : : PUNCT eurjchem-32 74 32     SPACE eurjchem-32 74 33 c c X eurjchem-32 74 34 , , PUNCT eurjchem-32 74 35     SPACE eurjchem-32 74 36 52.69 52.69 NUM eurjchem-32 74 37 ; ; PUNCT eurjchem-32 74 38     SPACE eurjchem-32 74 39 h h NOUN eurjchem-32 74 40 , , PUNCT eurjchem-32 74 41     SPACE eurjchem-32 74 42 4.07 4.07 NUM eurjchem-32 74 43 ; ; PUNCT eurjchem-32 74 44     SPACE eurjchem-32 74 45 n n CCONJ eurjchem-32 74 46 , , PUNCT eurjchem-32 74 47     SPACE eurjchem-32 74 48 25.65 25.65 NUM eurjchem-32 74 49 . . PUNCT eurjchem-32 74 50         SPACE eurjchem-32 74 51 2.11 2.11 NUM eurjchem-32 74 52 . . PUNCT eurjchem-32 74 53     SPACE eurjchem-32 75 1 2­(benzo[d]thiazol­2­yl)­3­hydroxy­3­(2­oxo­4­phenyl­ 2­(benzo[d]thiazol­2­yl)­3­hydroxy­3­(2­oxo­4­phenyl­ NUM eurjchem-32 75 2 1,2­dihydropyridin­3­yl)­ 1,2­dihydropyridin­3­yl)­ NUM eurjchem-32 75 3     SPACE eurjchem-32 75 4 acrylonitrile acrylonitrile NOUN eurjchem-32 75 5 , , PUNCT eurjchem-32 75 6     SPACE eurjchem-32 75 7 21 21 NUM eurjchem-32 75 8           SPACE eurjchem-32 75 9 to to ADP eurjchem-32 75 10     SPACE eurjchem-32 75 11 a a DET eurjchem-32 75 12     SPACE eurjchem-32 75 13 mixture mixture NOUN eurjchem-32 75 14     SPACE eurjchem-32 75 15 of of ADP eurjchem-32 75 16     SPACE eurjchem-32 75 17 4 4 NUM eurjchem-32 75 18     SPACE eurjchem-32 75 19 ( ( PUNCT eurjchem-32 75 20 2.41 2.41 NUM eurjchem-32 75 21     SPACE eurjchem-32 75 22 g g NOUN eurjchem-32 75 23 , , PUNCT eurjchem-32 75 24     SPACE eurjchem-32 75 25 0.01 0.01 NUM eurjchem-32 75 26     SPACE eurjchem-32 75 27 mol mol NOUN eurjchem-32 75 28 ) ) PUNCT eurjchem-32 75 29     SPACE eurjchem-32 75 30 and and CCONJ eurjchem-32 75 31     SPACE eurjchem-32 75 32 benzalacetophenone benzalacetophenone NOUN eurjchem-32 75 33     SPACE eurjchem-32 75 34 ( ( PUNCT eurjchem-32 75 35 2.08 2.08 NUM eurjchem-32 75 36     SPACE eurjchem-32 75 37 g g NOUN eurjchem-32 75 38 , , PUNCT eurjchem-32 75 39     SPACE eurjchem-32 75 40 0.01 0.01 NUM eurjchem-32 75 41     SPACE eurjchem-32 75 42 mol mol NOUN eurjchem-32 75 43 ) ) PUNCT eurjchem-32 75 44     SPACE eurjchem-32 75 45 in in ADP eurjchem-32 75 46     SPACE eurjchem-32 75 47 ethanol ethanol NOUN eurjchem-32 75 48     SPACE eurjchem-32 75 49 ( ( PUNCT eurjchem-32 75 50 20 20 NUM eurjchem-32 75 51     SPACE eurjchem-32 75 52 ml ml NOUN eurjchem-32 75 53 ) ) PUNCT eurjchem-32 75 54 , , PUNCT eurjchem-32 75 55     SPACE eurjchem-32 75 56 a a DET eurjchem-32 75 57     SPACE eurjchem-32 75 58 catalytic catalytic ADJ eurjchem-32 75 59     SPACE eurjchem-32 75 60 amount amount NOUN eurjchem-32 75 61     SPACE eurjchem-32 75 62 of of ADP eurjchem-32 75 63     SPACE eurjchem-32 75 64 piperidine piperidine NOUN eurjchem-32 75 65     SPACE eurjchem-32 75 66 was be AUX eurjchem-32 75 67     SPACE eurjchem-32 75 68 added add VERB eurjchem-32 75 69     SPACE eurjchem-32 75 70 ( ( PUNCT eurjchem-32 75 71 scheme scheme NOUN eurjchem-32 75 72     SPACE eurjchem-32 75 73 11 11 NUM eurjchem-32 75 74 ) ) PUNCT eurjchem-32 75 75 . . PUNCT eurjchem-32 75 76     SPACE eurjchem-32 76 1 the the DET eurjchem-32 76 2     SPACE eurjchem-32 76 3 reaction reaction NOUN eurjchem-32 76 4     SPACE eurjchem-32 76 5 mixture mixture NOUN eurjchem-32 76 6     SPACE eurjchem-32 76 7 was be AUX eurjchem-32 76 8     SPACE eurjchem-32 76 9 refluxed refluxe VERB eurjchem-32 76 10     SPACE eurjchem-32 76 11 for for ADP eurjchem-32 76 12     SPACE eurjchem-32 76 13 12 12 NUM eurjchem-32 76 14     SPACE eurjchem-32 76 15 h h NOUN eurjchem-32 76 16 , , PUNCT eurjchem-32 76 17     SPACE eurjchem-32 76 18 the the DET eurjchem-32 76 19     SPACE eurjchem-32 76 20 formed form VERB eurjchem-32 76 21     SPACE eurjchem-32 76 22 solid solid NOUN eurjchem-32 76 23     SPACE eurjchem-32 76 24 was be AUX eurjchem-32 76 25     SPACE eurjchem-32 76 26 left leave VERB eurjchem-32 76 27     SPACE eurjchem-32 76 28 to to PART eurjchem-32 76 29     SPACE eurjchem-32 76 30 cool cool VERB eurjchem-32 76 31     SPACE eurjchem-32 76 32 at at ADP eurjchem-32 76 33     SPACE eurjchem-32 76 34 room room NOUN eurjchem-32 76 35     SPACE eurjchem-32 76 36 temperature temperature NOUN eurjchem-32 76 37 , , PUNCT eurjchem-32 76 38     SPACE eurjchem-32 76 39 filtered filter VERB eurjchem-32 76 40     SPACE eurjchem-32 76 41 off off ADP eurjchem-32 76 42 , , PUNCT eurjchem-32 76 43     SPACE eurjchem-32 76 44 dried dry VERB eurjchem-32 76 45     SPACE eurjchem-32 76 46 and and CCONJ eurjchem-32 76 47     SPACE eurjchem-32 76 48 recrystallized recrystallize VERB eurjchem-32 76 49     SPACE eurjchem-32 76 50 from from ADP eurjchem-32 76 51     SPACE eurjchem-32 76 52 ethanol ethanol NOUN eurjchem-32 76 53     SPACE eurjchem-32 76 54 to to PART eurjchem-32 76 55     SPACE eurjchem-32 76 56 afford afford VERB eurjchem-32 76 57     SPACE eurjchem-32 76 58 2.53 2.53 NUM eurjchem-32 76 59     SPACE eurjchem-32 76 60 g g NOUN eurjchem-32 76 61     SPACE eurjchem-32 76 62 ( ( PUNCT eurjchem-32 76 63 68 68 NUM eurjchem-32 76 64 % % NOUN eurjchem-32 76 65 ) ) PUNCT eurjchem-32 76 66     SPACE eurjchem-32 76 67 of of ADP eurjchem-32 76 68     SPACE eurjchem-32 76 69 21 21 NUM eurjchem-32 76 70 ; ; PUNCT eurjchem-32 76 71     SPACE eurjchem-32 76 72 mp mp NOUN eurjchem-32 76 73     SPACE eurjchem-32 76 74 295 295 NUM eurjchem-32 76 75     SPACE eurjchem-32 76 76 oc oc NOUN eurjchem-32 76 77 ; ; PUNCT eurjchem-32 76 78     SPACE eurjchem-32 76 79 yellow yellow ADJ eurjchem-32 76 80     SPACE eurjchem-32 76 81 powder powder NOUN eurjchem-32 76 82 ; ; PUNCT eurjchem-32 76 83     SPACE eurjchem-32 76 84 ir ir PROPN eurjchem-32 76 85     SPACE eurjchem-32 76 86 ( ( PUNCT eurjchem-32 76 87 kbr kbr PROPN eurjchem-32 76 88 ) ) PUNCT eurjchem-32 76 89     SPACE eurjchem-32 76 90 ( ( PUNCT eurjchem-32 76 91 υ υ NOUN eurjchem-32 76 92 , , PUNCT eurjchem-32 76 93     SPACE eurjchem-32 76 94 cm‐1 cm‐1 NOUN eurjchem-32 76 95 ): ): PUNCT eurjchem-32 76 96     SPACE eurjchem-32 76 97 3441 3441 NUM eurjchem-32 76 98     SPACE eurjchem-32 76 99 ( ( PUNCT eurjchem-32 76 100 oh oh INTJ eurjchem-32 76 101 ) ) PUNCT eurjchem-32 76 102 , , PUNCT eurjchem-32 76 103     SPACE eurjchem-32 76 104 3134 3134 NUM eurjchem-32 76 105     SPACE eurjchem-32 76 106 ( ( PUNCT eurjchem-32 76 107 nh nh NOUN eurjchem-32 76 108 ) ) PUNCT eurjchem-32 76 109 , , PUNCT eurjchem-32 76 110     SPACE eurjchem-32 76 111 2211 2211 NUM eurjchem-32 76 112     SPACE eurjchem-32 76 113 ( ( PUNCT eurjchem-32 76 114 cn cn PROPN eurjchem-32 76 115 ) ) PUNCT eurjchem-32 76 116 , , PUNCT eurjchem-32 76 117     SPACE eurjchem-32 76 118 1631 1631 NUM eurjchem-32 76 119     SPACE eurjchem-32 76 120 ( ( PUNCT eurjchem-32 76 121 co co NOUN eurjchem-32 76 122 ) ) PUNCT eurjchem-32 76 123 . . PUNCT eurjchem-32 76 124     SPACE eurjchem-32 76 125 1h 1h NUM eurjchem-32 76 126     SPACE eurjchem-32 76 127 nmr nmr NOUN eurjchem-32 76 128     SPACE eurjchem-32 76 129 ( ( PUNCT eurjchem-32 76 130 dmso‐d6 dmso‐d6 NOUN eurjchem-32 76 131 ): ): PUNCT eurjchem-32 76 132     SPACE eurjchem-32 76 133 δ δ PROPN eurjchem-32 76 134 , , PUNCT eurjchem-32 76 135     SPACE eurjchem-32 76 136 7.41‐8.09 7.41‐8.09 NUM eurjchem-32 76 137     SPACE eurjchem-32 76 138 ( ( PUNCT eurjchem-32 76 139 m m PROPN eurjchem-32 76 140 , , PUNCT eurjchem-32 76 141     SPACE eurjchem-32 76 142 11h 11h NOUN eurjchem-32 76 143 , , PUNCT eurjchem-32 76 144     SPACE eurjchem-32 76 145 ar‐h ar‐h NOUN eurjchem-32 76 146 ) ) PUNCT eurjchem-32 76 147 , , PUNCT eurjchem-32 76 148     SPACE eurjchem-32 76 149 8.2 8.2 NUM eurjchem-32 76 150     SPACE eurjchem-32 76 151 ( ( PUNCT eurjchem-32 76 152 s s PROPN eurjchem-32 76 153 , , PUNCT eurjchem-32 76 154     SPACE eurjchem-32 76 155 1h 1h NUM eurjchem-32 76 156 , , PUNCT eurjchem-32 76 157     SPACE eurjchem-32 76 158 nh nh PROPN eurjchem-32 76 159 ) ) PUNCT eurjchem-32 76 160 , , PUNCT eurjchem-32 76 161     SPACE eurjchem-32 76 162 9.79 9.79 NUM eurjchem-32 76 163     SPACE eurjchem-32 76 164 ( ( PUNCT eurjchem-32 76 165 s s PROPN eurjchem-32 76 166 , , PUNCT eurjchem-32 76 167     SPACE eurjchem-32 76 168 1h 1h NUM eurjchem-32 76 169 , , PUNCT eurjchem-32 76 170     SPACE eurjchem-32 76 171 oh oh INTJ eurjchem-32 76 172 ) ) PUNCT eurjchem-32 76 173 . . PUNCT eurjchem-32 76 174     SPACE eurjchem-32 77 1 anal anal ADJ eurjchem-32 77 2 . . PUNCT eurjchem-32 77 3     SPACE eurjchem-32 77 4 calcd calcd NOUN eurjchem-32 77 5 . . PUNCT eurjchem-32 77 6     SPACE eurjchem-32 77 7 for for ADP eurjchem-32 77 8     SPACE eurjchem-32 77 9 c21h13n3o2s c21h13n3o2s NUM eurjchem-32 77 10 : : PUNCT eurjchem-32 77 11     SPACE eurjchem-32 77 12 c c X eurjchem-32 77 13 , , PUNCT eurjchem-32 77 14     SPACE eurjchem-32 77 15 67.91 67.91 NUM eurjchem-32 77 16 ; ; PUNCT eurjchem-32 77 17     SPACE eurjchem-32 77 18 h h NOUN eurjchem-32 77 19 , , PUNCT eurjchem-32 77 20     SPACE eurjchem-32 77 21 3.53 3.53 NUM eurjchem-32 77 22 ; ; PUNCT eurjchem-32 77 23     SPACE eurjchem-32 77 24 n n CCONJ eurjchem-32 77 25 , , PUNCT eurjchem-32 77 26     SPACE eurjchem-32 77 27 11.31 11.31 NUM eurjchem-32 77 28 . . PUNCT eurjchem-32 77 29     SPACE eurjchem-32 77 30 found find VERB eurjchem-32 77 31 : : PUNCT eurjchem-32 77 32     SPACE eurjchem-32 77 33 c c X eurjchem-32 77 34 , , PUNCT eurjchem-32 77 35     SPACE eurjchem-32 77 36 67.97 67.97 NUM eurjchem-32 77 37 ; ; PUNCT eurjchem-32 77 38     SPACE eurjchem-32 77 39 h h NOUN eurjchem-32 77 40 , , PUNCT eurjchem-32 77 41     SPACE eurjchem-32 77 42 3.56 3.56 NUM eurjchem-32 77 43 ; ; PUNCT eurjchem-32 77 44     SPACE eurjchem-32 77 45 n n CCONJ eurjchem-32 77 46 , , PUNCT eurjchem-32 77 47     SPACE eurjchem-32 77 48 11.39 11.39 NUM eurjchem-32 77 49 . . PUNCT eurjchem-32 77 50         SPACE eurjchem-32 77 51 scheme scheme NOUN eurjchem-32 77 52     SPACE eurjchem-32 77 53 11 11 NUM eurjchem-32 77 54             SPACE eurjchem-32 77 55 2.12 2.12 NUM eurjchem-32 77 56 . . PUNCT eurjchem-32 77 57     SPACE eurjchem-32 77 58 2­(5­amino­1,3­dimethyl­2,4­dioxo­1,2,3,4­tetrahydro­ 2­(5­amino­1,3­dimethyl­2,4­dioxo­1,2,3,4­tetrahydro­ NUM eurjchem-32 77 59 pyrido[2,3­d]pyrimidin­7­yl)­2­(benzo[d]thiazol­2­ pyrido[2,3­d]pyrimidin­7­yl)­2­(benzo[d]thiazol­2­ CCONJ eurjchem-32 77 60 yl)acetonitrile yl)acetonitrile PROPN eurjchem-32 77 61 , , PUNCT eurjchem-32 77 62     SPACE eurjchem-32 77 63 23 23 NUM eurjchem-32 77 64           SPACE eurjchem-32 77 65 to to ADP eurjchem-32 77 66     SPACE eurjchem-32 77 67 a a DET eurjchem-32 77 68     SPACE eurjchem-32 77 69 mixture mixture NOUN eurjchem-32 77 70     SPACE eurjchem-32 77 71 of of ADP eurjchem-32 77 72     SPACE eurjchem-32 77 73 4 4 NUM eurjchem-32 77 74     SPACE eurjchem-32 77 75 ( ( PUNCT eurjchem-32 77 76 2.41 2.41 NUM eurjchem-32 77 77     SPACE eurjchem-32 77 78 g g NOUN eurjchem-32 77 79 , , PUNCT eurjchem-32 77 80     SPACE eurjchem-32 77 81 0.01 0.01 NUM eurjchem-32 77 82     SPACE eurjchem-32 77 83 mol mol NOUN eurjchem-32 77 84 ) ) PUNCT eurjchem-32 77 85     SPACE eurjchem-32 77 86 and and CCONJ eurjchem-32 77 87     SPACE eurjchem-32 77 88 6‐amino‐1,3‐ 6‐amino‐1,3‐ NUM eurjchem-32 77 89 dimethylpyrimidine‐2,4(1h,3h)‐dione dimethylpyrimidine‐2,4(1h,3h)‐dione NOUN eurjchem-32 77 90     SPACE eurjchem-32 77 91 ( ( PUNCT eurjchem-32 77 92 13 13 NUM eurjchem-32 77 93 ) ) PUNCT eurjchem-32 77 94     SPACE eurjchem-32 77 95 ( ( PUNCT eurjchem-32 77 96 1.55 1.55 NUM eurjchem-32 77 97     SPACE eurjchem-32 77 98 g g NOUN eurjchem-32 77 99 , , PUNCT eurjchem-32 77 100     SPACE eurjchem-32 77 101 0.01 0.01 NUM eurjchem-32 77 102     SPACE eurjchem-32 77 103 mol mol NOUN eurjchem-32 77 104 ) ) PUNCT eurjchem-32 77 105     SPACE eurjchem-32 77 106 in in ADP eurjchem-32 77 107     SPACE eurjchem-32 77 108 glacial glacial ADJ eurjchem-32 77 109     SPACE eurjchem-32 77 110 acetic acetic ADJ eurjchem-32 77 111     SPACE eurjchem-32 77 112 acid acid NOUN eurjchem-32 77 113     SPACE eurjchem-32 77 114 ( ( PUNCT eurjchem-32 77 115 20 20 NUM eurjchem-32 77 116     SPACE eurjchem-32 77 117 ml ml NOUN eurjchem-32 77 118 ) ) PUNCT eurjchem-32 77 119 , , PUNCT eurjchem-32 77 120     SPACE eurjchem-32 77 121 freshly freshly ADV eurjchem-32 77 122     SPACE eurjchem-32 77 123 fused fuse VERB eurjchem-32 77 124     SPACE eurjchem-32 77 125 sodium sodium NOUN eurjchem-32 77 126     SPACE eurjchem-32 77 127 acetate acetate NOUN eurjchem-32 77 128     SPACE eurjchem-32 77 129 ( ( PUNCT eurjchem-32 77 130 1.23 1.23 NUM eurjchem-32 77 131     SPACE eurjchem-32 77 132 g g NOUN eurjchem-32 77 133 , , PUNCT eurjchem-32 77 134     SPACE eurjchem-32 77 135 0.015 0.015 NUM eurjchem-32 77 136     SPACE eurjchem-32 77 137 mol mol NOUN eurjchem-32 77 138 ) ) PUNCT eurjchem-32 77 139     SPACE eurjchem-32 77 140 was be AUX eurjchem-32 77 141     SPACE eurjchem-32 77 142 added add VERB eurjchem-32 77 143     SPACE eurjchem-32 77 144 ( ( PUNCT eurjchem-32 77 145 scheme scheme NOUN eurjchem-32 77 146     SPACE eurjchem-32 77 147 12 12 NUM eurjchem-32 77 148 ) ) PUNCT eurjchem-32 77 149 . . PUNCT eurjchem-32 77 150     SPACE eurjchem-32 78 1 the the DET eurjchem-32 78 2     SPACE eurjchem-32 78 3 reaction reaction NOUN eurjchem-32 78 4     SPACE eurjchem-32 78 5 mixture mixture NOUN eurjchem-32 78 6     SPACE eurjchem-32 78 7 was be AUX eurjchem-32 78 8     SPACE eurjchem-32 78 9 refluxed refluxe VERB eurjchem-32 78 10     SPACE eurjchem-32 78 11 for for ADP eurjchem-32 78 12     SPACE eurjchem-32 78 13 12 12 NUM eurjchem-32 78 14     SPACE eurjchem-32 78 15 h h NOUN eurjchem-32 78 16 , , PUNCT eurjchem-32 78 17     SPACE eurjchem-32 78 18 left leave VERB eurjchem-32 78 19     SPACE eurjchem-32 78 20 to to PART eurjchem-32 78 21     SPACE eurjchem-32 78 22 cool cool VERB eurjchem-32 78 23     SPACE eurjchem-32 78 24 at at ADP eurjchem-32 78 25     SPACE eurjchem-32 78 26 room room NOUN eurjchem-32 78 27     SPACE eurjchem-32 78 28 temperature temperature NOUN eurjchem-32 78 29 , , PUNCT eurjchem-32 78 30     SPACE eurjchem-32 78 31 poured pour VERB eurjchem-32 78 32     SPACE eurjchem-32 78 33 into into ADP eurjchem-32 78 34     SPACE eurjchem-32 78 35 ice ice NOUN eurjchem-32 78 36     SPACE eurjchem-32 78 37 cold cold ADJ eurjchem-32 78 38     SPACE eurjchem-32 78 39 water water NOUN eurjchem-32 78 40 . . PUNCT eurjchem-32 78 41     SPACE eurjchem-32 79 1 the the DET eurjchem-32 79 2     SPACE eurjchem-32 79 3 precipitated precipitate VERB eurjchem-32 79 4     SPACE eurjchem-32 79 5 solid solid NOUN eurjchem-32 79 6     SPACE eurjchem-32 79 7 after after SCONJ eurjchem-32 79 8     SPACE eurjchem-32 79 9 neutralization neutralization NOUN eurjchem-32 79 10     SPACE eurjchem-32 79 11 was be AUX eurjchem-32 79 12     SPACE eurjchem-32 79 13 filtered filter VERB eurjchem-32 79 14     SPACE eurjchem-32 79 15 off off ADP eurjchem-32 79 16 , , PUNCT eurjchem-32 79 17     SPACE eurjchem-32 79 18 dried dry VERB eurjchem-32 79 19     SPACE eurjchem-32 79 20 and and CCONJ eurjchem-32 79 21     SPACE eurjchem-32 79 22 recrystallized recrystallize VERB eurjchem-32 79 23     SPACE eurjchem-32 79 24 from from ADP eurjchem-32 79 25     SPACE eurjchem-32 79 26 ethanol ethanol NOUN eurjchem-32 79 27     SPACE eurjchem-32 79 28 to to PART eurjchem-32 79 29     SPACE eurjchem-32 79 30 afford afford VERB eurjchem-32 79 31     SPACE eurjchem-32 79 32 3.1 3.1 NUM eurjchem-32 79 33     SPACE eurjchem-32 79 34 g g NOUN eurjchem-32 79 35     SPACE eurjchem-32 79 36 ( ( PUNCT eurjchem-32 79 37 82 82 NUM eurjchem-32 79 38 % % NOUN eurjchem-32 79 39 ) ) PUNCT eurjchem-32 79 40     SPACE eurjchem-32 79 41 of of ADP eurjchem-32 79 42     SPACE eurjchem-32 79 43 23 23 NUM eurjchem-32 79 44 ; ; PUNCT eurjchem-32 79 45     SPACE eurjchem-32 79 46 mp mp NOUN eurjchem-32 79 47     SPACE eurjchem-32 79 48 260 260 NUM eurjchem-32 79 49     SPACE eurjchem-32 79 50 oc oc NOUN eurjchem-32 79 51 ; ; PUNCT eurjchem-32 79 52     SPACE eurjchem-32 79 53 yellow yellow ADJ eurjchem-32 79 54     SPACE eurjchem-32 79 55 powder powder NOUN eurjchem-32 79 56 ; ; PUNCT eurjchem-32 79 57     SPACE eurjchem-32 79 58 ir ir PROPN eurjchem-32 79 59     SPACE eurjchem-32 79 60 ( ( PUNCT eurjchem-32 79 61 kbr kbr PROPN eurjchem-32 79 62 ) ) PUNCT eurjchem-32 79 63     SPACE eurjchem-32 79 64 ( ( PUNCT eurjchem-32 79 65 υ υ NOUN eurjchem-32 79 66 , , PUNCT eurjchem-32 79 67     SPACE eurjchem-32 79 68 cm‐1 cm‐1 NOUN eurjchem-32 79 69 ): ): PUNCT eurjchem-32 79 70         SPACE eurjchem-32 79 71 3418 3418 NUM eurjchem-32 79 72 , , PUNCT eurjchem-32 79 73     SPACE eurjchem-32 79 74 3581 3581 NUM eurjchem-32 79 75     SPACE eurjchem-32 79 76 ( ( PUNCT eurjchem-32 79 77 nh2 nh2 PROPN eurjchem-32 79 78 ) ) PUNCT eurjchem-32 79 79 , , PUNCT eurjchem-32 79 80     SPACE eurjchem-32 79 81 2216 2216 NUM eurjchem-32 79 82     SPACE eurjchem-32 79 83 ( ( PUNCT eurjchem-32 79 84 cn cn PROPN eurjchem-32 79 85 ) ) PUNCT eurjchem-32 79 86 . . PUNCT eurjchem-32 79 87     SPACE eurjchem-32 79 88 1h 1h NUM eurjchem-32 79 89     SPACE eurjchem-32 79 90 nmr nmr NOUN eurjchem-32 79 91     SPACE eurjchem-32 79 92 ( ( PUNCT eurjchem-32 79 93 dmso‐d6 dmso‐d6 NOUN eurjchem-32 79 94 ): ): PUNCT eurjchem-32 79 95     SPACE eurjchem-32 79 96 δ δ PROPN eurjchem-32 79 97 , , PUNCT eurjchem-32 79 98     SPACE eurjchem-32 79 99 3.25 3.25 NUM eurjchem-32 79 100     SPACE eurjchem-32 79 101 ( ( PUNCT eurjchem-32 79 102 s s PROPN eurjchem-32 79 103 , , PUNCT eurjchem-32 79 104     SPACE eurjchem-32 79 105 3h 3h NUM eurjchem-32 79 106 , , PUNCT eurjchem-32 79 107     SPACE eurjchem-32 79 108 ch3 ch3 PROPN eurjchem-32 79 109 ) ) PUNCT eurjchem-32 79 110 , , PUNCT eurjchem-32 79 111     SPACE eurjchem-32 79 112 3.37 3.37 NUM eurjchem-32 79 113     SPACE eurjchem-32 79 114 ( ( PUNCT eurjchem-32 79 115 s s PROPN eurjchem-32 79 116 , , PUNCT eurjchem-32 79 117     SPACE eurjchem-32 79 118 3h 3h NUM eurjchem-32 79 119 , , PUNCT eurjchem-32 79 120     SPACE eurjchem-32 79 121 ch3 ch3 PROPN eurjchem-32 79 122 ) ) PUNCT eurjchem-32 79 123 , , PUNCT eurjchem-32 79 124     SPACE eurjchem-32 79 125 4.89 4.89 NUM eurjchem-32 79 126     SPACE eurjchem-32 79 127 ( ( PUNCT eurjchem-32 79 128 s s PROPN eurjchem-32 79 129 , , PUNCT eurjchem-32 79 130     SPACE eurjchem-32 79 131 1h 1h NUM eurjchem-32 79 132 , , PUNCT eurjchem-32 79 133     SPACE eurjchem-32 79 134 ch ch NOUN eurjchem-32 79 135 ) ) PUNCT eurjchem-32 79 136 , , PUNCT eurjchem-32 79 137     SPACE eurjchem-32 79 138 5.9 5.9 NUM eurjchem-32 79 139     SPACE eurjchem-32 79 140 ( ( PUNCT eurjchem-32 79 141 s s PROPN eurjchem-32 79 142 , , PUNCT eurjchem-32 79 143     SPACE eurjchem-32 79 144 1h 1h NUM eurjchem-32 79 145 , , PUNCT eurjchem-32 79 146     SPACE eurjchem-32 79 147 c3‐h c3‐h VERB eurjchem-32 79 148 , , PUNCT eurjchem-32 79 149     SPACE eurjchem-32 79 150 pyridine pyridine NOUN eurjchem-32 79 151 ) ) PUNCT eurjchem-32 79 152 , , PUNCT eurjchem-32 79 153     SPACE eurjchem-32 79 154 6.22 6.22 NUM eurjchem-32 79 155     SPACE eurjchem-32 79 156 ( ( PUNCT eurjchem-32 79 157 br br PROPN eurjchem-32 79 158 . . PROPN eurjchem-32 79 159 , , PUNCT eurjchem-32 79 160     SPACE eurjchem-32 79 161 2h 2h NUM eurjchem-32 79 162 , , PUNCT eurjchem-32 79 163     SPACE eurjchem-32 79 164 nh2 nh2 PROPN eurjchem-32 79 165 ) ) PUNCT eurjchem-32 79 166 , , PUNCT eurjchem-32 79 167     SPACE eurjchem-32 79 168 7.30‐8.10 7.30‐8.10 NUM eurjchem-32 79 169     SPACE eurjchem-32 79 170 ( ( PUNCT eurjchem-32 79 171 m m PROPN eurjchem-32 79 172 , , PUNCT eurjchem-32 79 173     SPACE eurjchem-32 79 174 4h 4h NOUN eurjchem-32 79 175 , , PUNCT eurjchem-32 79 176     SPACE eurjchem-32 79 177 ar‐h ar‐h NOUN eurjchem-32 79 178 ) ) PUNCT eurjchem-32 79 179 . . PUNCT eurjchem-32 79 180     SPACE eurjchem-32 80 1 ms ms NOUN eurjchem-32 80 2 : : PUNCT eurjchem-32 80 3     SPACE eurjchem-32 80 4 ( ( PUNCT eurjchem-32 80 5 m m PROPN eurjchem-32 80 6 / / SYM eurjchem-32 80 7 z z NOUN eurjchem-32 80 8 , , PUNCT eurjchem-32 80 9     SPACE eurjchem-32 80 10 % % NOUN eurjchem-32 80 11 ): ): PUNCT eurjchem-32 80 12     SPACE eurjchem-32 80 13 348 348 NUM eurjchem-32 80 14     SPACE eurjchem-32 80 15 ( ( PUNCT eurjchem-32 80 16 m+‐2ch3 m+‐2ch3 ADJ eurjchem-32 80 17 , , PUNCT eurjchem-32 80 18     SPACE eurjchem-32 80 19 15.8 15.8 NUM eurjchem-32 80 20 ) ) PUNCT eurjchem-32 80 21 , , PUNCT eurjchem-32 80 22     SPACE eurjchem-32 80 23 202 202 NUM eurjchem-32 80 24     SPACE eurjchem-32 80 25 ( ( PUNCT eurjchem-32 80 26 2.6 2.6 NUM eurjchem-32 80 27 ) ) PUNCT eurjchem-32 80 28 , , PUNCT eurjchem-32 80 29     SPACE eurjchem-32 80 30 115 115 NUM eurjchem-32 80 31     SPACE eurjchem-32 80 32 ( ( PUNCT eurjchem-32 80 33 21.1 21.1 NUM eurjchem-32 80 34 ) ) PUNCT eurjchem-32 80 35 , , PUNCT eurjchem-32 80 36     SPACE eurjchem-32 80 37 97 97 NUM eurjchem-32 80 38     SPACE eurjchem-32 80 39 ( ( PUNCT eurjchem-32 80 40 47.4 47.4 NUM eurjchem-32 80 41 ) ) PUNCT eurjchem-32 80 42 , , PUNCT eurjchem-32 80 43     SPACE eurjchem-32 80 44 56 56 NUM eurjchem-32 80 45     SPACE eurjchem-32 80 46 ( ( PUNCT eurjchem-32 80 47 100.0 100.0 NUM eurjchem-32 80 48 ) ) PUNCT eurjchem-32 80 49 . . PUNCT eurjchem-32 80 50     SPACE eurjchem-32 81 1 anal anal ADJ eurjchem-32 81 2 . . PUNCT eurjchem-32 81 3     SPACE eurjchem-32 81 4 calcd calcd NOUN eurjchem-32 81 5 . . PUNCT eurjchem-32 81 6     SPACE eurjchem-32 82 1 for for ADP eurjchem-32 82 2     SPACE eurjchem-32 82 3 c18h14n6o2s c18h14n6o2s PROPN eurjchem-32 82 4 : : PUNCT eurjchem-32 82 5     SPACE eurjchem-32 82 6 c c X eurjchem-32 82 7 , , PUNCT eurjchem-32 82 8     SPACE eurjchem-32 82 9 57.13 57.13 NUM eurjchem-32 82 10 ; ; PUNCT eurjchem-32 82 11     SPACE eurjchem-32 82 12 h h NOUN eurjchem-32 82 13 , , PUNCT eurjchem-32 82 14     SPACE eurjchem-32 82 15 3.73 3.73 NUM eurjchem-32 82 16 ; ; PUNCT eurjchem-32 82 17     SPACE eurjchem-32 82 18 n n CCONJ eurjchem-32 82 19 , , PUNCT eurjchem-32 82 20     SPACE eurjchem-32 82 21 22.21 22.21 NUM eurjchem-32 82 22 . . PUNCT eurjchem-32 82 23     SPACE eurjchem-32 82 24 found find VERB eurjchem-32 82 25 : : PUNCT eurjchem-32 82 26     SPACE eurjchem-32 82 27 c c X eurjchem-32 82 28 , , PUNCT eurjchem-32 82 29     SPACE eurjchem-32 82 30 57.21 57.21 NUM eurjchem-32 82 31 ; ; PUNCT eurjchem-32 82 32     SPACE eurjchem-32 82 33 h h NOUN eurjchem-32 82 34 , , PUNCT eurjchem-32 82 35     SPACE eurjchem-32 82 36 3.81 3.81 NUM eurjchem-32 82 37 ; ; PUNCT eurjchem-32 82 38     SPACE eurjchem-32 82 39 n n CCONJ eurjchem-32 82 40 , , PUNCT eurjchem-32 82 41     SPACE eurjchem-32 82 42 22.28 22.28 NUM eurjchem-32 82 43 . . PUNCT eurjchem-32 82 44         SPACE eurjchem-32 82 45 scheme scheme NOUN eurjchem-32 82 46     SPACE eurjchem-32 82 47 12 12 NUM eurjchem-32 82 48     SPACE eurjchem-32 82 49 2.13 2.13 NUM eurjchem-32 82 50 . . PUNCT eurjchem-32 82 51     SPACE eurjchem-32 83 1 5­amino­4­(benzo[d]thiazol­2­yl)­3­hydroxythiophene­ 5­amino­4­(benzo[d]thiazol­2­yl)­3­hydroxythiophene­ NOUN eurjchem-32 83 2 2­carbonitrile 2­carbonitrile NUM eurjchem-32 83 3 , , PUNCT eurjchem-32 83 4     SPACE eurjchem-32 83 5 24 24 NUM eurjchem-32 83 6           SPACE eurjchem-32 83 7 a a DET eurjchem-32 83 8     SPACE eurjchem-32 83 9 mixture mixture NOUN eurjchem-32 83 10     SPACE eurjchem-32 83 11 of of ADP eurjchem-32 83 12     SPACE eurjchem-32 83 13 4 4 NUM eurjchem-32 83 14     SPACE eurjchem-32 83 15 ( ( PUNCT eurjchem-32 83 16 2.41 2.41 NUM eurjchem-32 83 17     SPACE eurjchem-32 83 18 g g NOUN eurjchem-32 83 19 , , PUNCT eurjchem-32 83 20     SPACE eurjchem-32 83 21 0.01 0.01 NUM eurjchem-32 83 22     SPACE eurjchem-32 83 23 mol mol NOUN eurjchem-32 83 24 ) ) PUNCT eurjchem-32 83 25 , , PUNCT eurjchem-32 83 26     SPACE eurjchem-32 83 27 orthorhombic orthorhombic NOUN eurjchem-32 83 28     SPACE eurjchem-32 83 29 sulfur sulfur NOUN eurjchem-32 83 30     SPACE eurjchem-32 83 31 ( ( PUNCT eurjchem-32 83 32 0.32 0.32 NUM eurjchem-32 83 33     SPACE eurjchem-32 83 34 g g NOUN eurjchem-32 83 35 , , PUNCT eurjchem-32 83 36     SPACE eurjchem-32 83 37 0.01 0.01 NUM eurjchem-32 83 38     SPACE eurjchem-32 83 39 mol mol NOUN eurjchem-32 83 40 ) ) PUNCT eurjchem-32 83 41 , , PUNCT eurjchem-32 83 42     SPACE eurjchem-32 83 43 and and CCONJ eurjchem-32 83 44     SPACE eurjchem-32 83 45 tea tea NOUN eurjchem-32 83 46     SPACE eurjchem-32 83 47 ( ( PUNCT eurjchem-32 83 48 3 3 NOUN eurjchem-32 83 49     SPACE eurjchem-32 83 50 ml ml NOUN eurjchem-32 83 51 ) ) PUNCT eurjchem-32 83 52     SPACE eurjchem-32 83 53 were be AUX eurjchem-32 83 54     SPACE eurjchem-32 83 55 kept keep VERB eurjchem-32 83 56     SPACE eurjchem-32 83 57 on on ADP eurjchem-32 83 58     SPACE eurjchem-32 83 59 a a DET eurjchem-32 83 60     SPACE eurjchem-32 83 61 water water NOUN eurjchem-32 83 62     SPACE eurjchem-32 83 63 bath bath NOUN eurjchem-32 83 64     SPACE eurjchem-32 83 65 at at ADP eurjchem-32 83 66     SPACE eurjchem-32 83 67 50‐ 50‐ NUM eurjchem-32 83 68 60 60 NUM eurjchem-32 83 69     SPACE eurjchem-32 83 70 oc oc NOUN eurjchem-32 83 71     SPACE eurjchem-32 83 72 for for ADP eurjchem-32 83 73     SPACE eurjchem-32 83 74 5 5 NUM eurjchem-32 83 75     SPACE eurjchem-32 83 76 h h NOUN eurjchem-32 83 77 , , PUNCT eurjchem-32 83 78     SPACE eurjchem-32 83 79 left leave VERB eurjchem-32 83 80     SPACE eurjchem-32 83 81 to to PART eurjchem-32 83 82     SPACE eurjchem-32 83 83 cool cool VERB eurjchem-32 83 84     SPACE eurjchem-32 83 85 then then ADV eurjchem-32 83 86     SPACE eurjchem-32 83 87 poured pour VERB eurjchem-32 83 88     SPACE eurjchem-32 83 89 into into ADP eurjchem-32 83 90     SPACE eurjchem-32 83 91 ice ice NOUN eurjchem-32 83 92     SPACE eurjchem-32 83 93 cold cold ADJ eurjchem-32 83 94     SPACE eurjchem-32 83 95 water water NOUN eurjchem-32 83 96     SPACE eurjchem-32 83 97 and and CCONJ eurjchem-32 83 98     SPACE eurjchem-32 83 99 acidified acidify VERB eurjchem-32 83 100     SPACE eurjchem-32 83 101 by by ADP eurjchem-32 83 102     SPACE eurjchem-32 83 103 conc conc NOUN eurjchem-32 83 104 . . PUNCT eurjchem-32 83 105     SPACE eurjchem-32 84 1 hcl hcl PROPN eurjchem-32 84 2     SPACE eurjchem-32 84 3 ( ( PUNCT eurjchem-32 84 4 scheme scheme NOUN eurjchem-32 84 5     SPACE eurjchem-32 84 6 13 13 NUM eurjchem-32 84 7 ) ) PUNCT eurjchem-32 84 8 . . PUNCT eurjchem-32 84 9     SPACE eurjchem-32 85 1 the the DET eurjchem-32 85 2     SPACE eurjchem-32 85 3 formed form VERB eurjchem-32 85 4     SPACE eurjchem-32 85 5 solid solid NOUN eurjchem-32 85 6     SPACE eurjchem-32 85 7 was be AUX eurjchem-32 85 8     SPACE eurjchem-32 85 9 filtered filter VERB eurjchem-32 85 10     SPACE eurjchem-32 85 11 off off ADP eurjchem-32 85 12 , , PUNCT eurjchem-32 85 13     SPACE eurjchem-32 85 14 dried dry VERB eurjchem-32 85 15     SPACE eurjchem-32 85 16 and and CCONJ eurjchem-32 85 17     SPACE eurjchem-32 85 18 recrystallized recrystallize VERB eurjchem-32 85 19     SPACE eurjchem-32 85 20 from from ADP eurjchem-32 85 21     SPACE eurjchem-32 85 22 ethanol ethanol NOUN eurjchem-32 85 23     SPACE eurjchem-32 85 24 to to PART eurjchem-32 85 25     SPACE eurjchem-32 85 26 afford afford VERB eurjchem-32 85 27     SPACE eurjchem-32 85 28 2.19 2.19 NUM eurjchem-32 85 29     SPACE eurjchem-32 85 30 g g NOUN eurjchem-32 85 31     SPACE eurjchem-32 85 32 ( ( PUNCT eurjchem-32 85 33 80 80 NUM eurjchem-32 85 34 % % NOUN eurjchem-32 85 35 ) ) PUNCT eurjchem-32 85 36     SPACE eurjchem-32 85 37 of of ADP eurjchem-32 85 38     SPACE eurjchem-32 85 39 24 24 NUM eurjchem-32 85 40 ; ; PUNCT eurjchem-32 85 41     SPACE eurjchem-32 85 42 mp mp NOUN eurjchem-32 85 43     SPACE eurjchem-32 85 44 208 208 NUM eurjchem-32 85 45     SPACE eurjchem-32 85 46 oc oc NOUN eurjchem-32 85 47 ; ; PUNCT eurjchem-32 85 48     SPACE eurjchem-32 85 49 orange orange NOUN eurjchem-32 85 50     SPACE eurjchem-32 85 51 powder powder NOUN eurjchem-32 85 52 ; ; PUNCT eurjchem-32 85 53     SPACE eurjchem-32 85 54 ir ir PROPN eurjchem-32 85 55     SPACE eurjchem-32 85 56 ( ( PUNCT eurjchem-32 85 57 kbr kbr PROPN eurjchem-32 85 58 ) ) PUNCT eurjchem-32 85 59     SPACE eurjchem-32 85 60 ( ( PUNCT eurjchem-32 85 61 υ υ NOUN eurjchem-32 85 62 , , PUNCT eurjchem-32 85 63     SPACE eurjchem-32 85 64 cm‐1 cm‐1 NOUN eurjchem-32 85 65 ): ): PUNCT eurjchem-32 85 66     SPACE eurjchem-32 85 67 3454 3454 NUM eurjchem-32 85 68     SPACE eurjchem-32 85 69 ( ( PUNCT eurjchem-32 85 70 oh oh INTJ eurjchem-32 85 71 ) ) PUNCT eurjchem-32 85 72 , , PUNCT eurjchem-32 85 73     SPACE eurjchem-32 85 74 3396 3396 NUM eurjchem-32 85 75 , , PUNCT eurjchem-32 85 76     SPACE eurjchem-32 85 77 3345 3345 NUM eurjchem-32 85 78     SPACE eurjchem-32 85 79 ( ( PUNCT eurjchem-32 85 80 nh2 nh2 PROPN eurjchem-32 85 81 ) ) PUNCT eurjchem-32 85 82 . . PUNCT eurjchem-32 85 83     SPACE eurjchem-32 86 1 1h 1h NUM eurjchem-32 86 2     SPACE eurjchem-32 86 3 nmr nmr NOUN eurjchem-32 86 4     SPACE eurjchem-32 86 5 ( ( PUNCT eurjchem-32 86 6 dmso‐d6 dmso‐d6 NOUN eurjchem-32 86 7 ): ): PUNCT eurjchem-32 86 8     SPACE eurjchem-32 86 9 δ δ PROPN eurjchem-32 86 10 , , PUNCT eurjchem-32 86 11     SPACE eurjchem-32 86 12 6.12 6.12 NUM eurjchem-32 86 13     SPACE eurjchem-32 86 14 ( ( PUNCT eurjchem-32 86 15 s s PROPN eurjchem-32 86 16 , , PUNCT eurjchem-32 86 17     SPACE eurjchem-32 86 18 br br NOUN eurjchem-32 86 19 . . PROPN eurjchem-32 86 20 , , PUNCT eurjchem-32 86 21     SPACE eurjchem-32 86 22 1h 1h NUM eurjchem-32 86 23 , , PUNCT eurjchem-32 86 24     SPACE eurjchem-32 86 25 oh oh INTJ eurjchem-32 86 26 ) ) PUNCT eurjchem-32 86 27 , , PUNCT eurjchem-32 86 28     SPACE eurjchem-32 86 29 6.67 6.67 NUM eurjchem-32 86 30     SPACE eurjchem-32 86 31 ( ( PUNCT eurjchem-32 86 32 s s PROPN eurjchem-32 86 33 , , PUNCT eurjchem-32 86 34     SPACE eurjchem-32 86 35 br br PROPN eurjchem-32 86 36 . . PROPN eurjchem-32 86 37 , , PUNCT eurjchem-32 86 38     SPACE eurjchem-32 86 39 2h 2h NUM eurjchem-32 86 40 , , PUNCT eurjchem-32 86 41     SPACE eurjchem-32 86 42 nh2 nh2 PROPN eurjchem-32 86 43 ) ) PUNCT eurjchem-32 86 44 , , PUNCT eurjchem-32 86 45     SPACE eurjchem-32 86 46 7.21‐8.32 7.21‐8.32 NUM eurjchem-32 86 47     SPACE eurjchem-32 86 48 ( ( PUNCT eurjchem-32 86 49 m m PROPN eurjchem-32 86 50 , , PUNCT eurjchem-32 86 51     SPACE eurjchem-32 86 52 4h 4h NOUN eurjchem-32 86 53 , , PUNCT eurjchem-32 86 54     SPACE eurjchem-32 86 55 ar‐h ar‐h NOUN eurjchem-32 86 56 ) ) PUNCT eurjchem-32 86 57 . . PUNCT eurjchem-32 86 58     SPACE eurjchem-32 86 59 13c 13c NOUN eurjchem-32 86 60     SPACE eurjchem-32 86 61 nmr nmr NOUN eurjchem-32 86 62     SPACE eurjchem-32 86 63 ( ( PUNCT eurjchem-32 86 64 dmso‐d6 dmso‐d6 NOUN eurjchem-32 86 65 ): ): PUNCT eurjchem-32 86 66     SPACE eurjchem-32 86 67 δ δ PROPN eurjchem-32 86 68 , , PUNCT eurjchem-32 86 69     SPACE eurjchem-32 86 70 180.14 180.14 NUM eurjchem-32 86 71 , , PUNCT eurjchem-32 86 72     SPACE eurjchem-32 86 73 179.62 179.62 NUM eurjchem-32 86 74 , , PUNCT eurjchem-32 86 75     SPACE eurjchem-32 86 76 166.77 166.77 NUM eurjchem-32 86 77 , , PUNCT eurjchem-32 86 78     SPACE eurjchem-32 86 79 159.64 159.64 NUM eurjchem-32 86 80 , , PUNCT eurjchem-32 86 81     SPACE eurjchem-32 86 82 139.49 139.49 NUM eurjchem-32 86 83 , , PUNCT eurjchem-32 86 84     SPACE eurjchem-32 86 85 139.00 139.00 NUM eurjchem-32 86 86 , , PUNCT eurjchem-32 86 87     SPACE eurjchem-32 86 88 134.16 134.16 NUM eurjchem-32 86 89 , , PUNCT eurjchem-32 86 90     SPACE eurjchem-32 86 91 130.25 130.25 NUM eurjchem-32 86 92 , , PUNCT eurjchem-32 86 93     SPACE eurjchem-32 86 94 128.97 128.97 NUM eurjchem-32 86 95 , , PUNCT eurjchem-32 86 96     SPACE eurjchem-32 86 97 127.54 127.54 NUM eurjchem-32 86 98 , , PUNCT eurjchem-32 86 99     SPACE eurjchem-32 86 100 125.60 125.60 NUM eurjchem-32 86 101 , , PUNCT eurjchem-32 86 102     SPACE eurjchem-32 86 103 124.44 124.44 NUM eurjchem-32 86 104 , , PUNCT eurjchem-32 86 105     SPACE eurjchem-32 86 106 123.65 123.65 NUM eurjchem-32 86 107 , , PUNCT eurjchem-32 86 108     SPACE eurjchem-32 86 109 122.83 122.83 NUM eurjchem-32 86 110 , , PUNCT eurjchem-32 86 111     SPACE eurjchem-32 86 112 117.90 117.90 NUM eurjchem-32 86 113 , , PUNCT eurjchem-32 86 114     SPACE eurjchem-32 86 115 115.93 115.93 NUM eurjchem-32 86 116 , , PUNCT eurjchem-32 86 117     SPACE eurjchem-32 86 118 112.40 112.40 NUM eurjchem-32 86 119 , , PUNCT eurjchem-32 86 120     SPACE eurjchem-32 86 121 84.65 84.65 NUM eurjchem-32 86 122 , , PUNCT eurjchem-32 86 123     SPACE eurjchem-32 86 124 75.48 75.48 NUM eurjchem-32 86 125 , , PUNCT eurjchem-32 86 126     SPACE eurjchem-32 86 127 45.75 45.75 NUM eurjchem-32 86 128 , , PUNCT eurjchem-32 86 129     SPACE eurjchem-32 86 130 39.84 39.84 NUM eurjchem-32 86 131 , , PUNCT eurjchem-32 86 132     SPACE eurjchem-32 86 133 30.73 30.73 NUM eurjchem-32 86 134 , , PUNCT eurjchem-32 86 135     SPACE eurjchem-32 86 136 29.4 29.4 NUM eurjchem-32 86 137 . . PUNCT eurjchem-32 86 138     SPACE eurjchem-32 87 1 ms ms NOUN eurjchem-32 87 2 : : PUNCT eurjchem-32 87 3     SPACE eurjchem-32 87 4 ( ( PUNCT eurjchem-32 87 5 m m PROPN eurjchem-32 87 6 / / SYM eurjchem-32 87 7 z z NOUN eurjchem-32 87 8 , , PUNCT eurjchem-32 87 9     SPACE eurjchem-32 87 10 % % NOUN eurjchem-32 87 11 ): ): PUNCT eurjchem-32 87 12     SPACE eurjchem-32 87 13 274 274 NUM eurjchem-32 87 14     SPACE eurjchem-32 87 15 ( ( PUNCT eurjchem-32 87 16 m+‐1 m+‐1 PROPN eurjchem-32 87 17 , , PUNCT eurjchem-32 87 18     SPACE eurjchem-32 87 19 26.1 26.1 NUM eurjchem-32 87 20 ) ) PUNCT eurjchem-32 87 21 , , PUNCT eurjchem-32 87 22     SPACE eurjchem-32 87 23 258 258 NUM eurjchem-32 87 24     SPACE eurjchem-32 87 25 ( ( PUNCT eurjchem-32 87 26 30.4 30.4 NUM eurjchem-32 87 27 ) ) PUNCT eurjchem-32 87 28 , , PUNCT eurjchem-32 87 29     SPACE eurjchem-32 87 30 201 201 NUM eurjchem-32 87 31     SPACE eurjchem-32 87 32 ( ( PUNCT eurjchem-32 87 33 100.0 100.0 NUM eurjchem-32 87 34 ) ) PUNCT eurjchem-32 87 35 , , PUNCT eurjchem-32 87 36     SPACE eurjchem-32 87 37 173 173 NUM eurjchem-32 87 38     SPACE eurjchem-32 87 39 ( ( PUNCT eurjchem-32 87 40 56.5 56.5 NUM eurjchem-32 87 41 ) ) PUNCT eurjchem-32 87 42 , , PUNCT eurjchem-32 87 43     SPACE eurjchem-32 87 44 146 146 NUM eurjchem-32 87 45     SPACE eurjchem-32 87 46 ( ( PUNCT eurjchem-32 87 47 47.8 47.8 NUM eurjchem-32 87 48 ) ) PUNCT eurjchem-32 87 49 , , PUNCT eurjchem-32 87 50     SPACE eurjchem-32 87 51 122 122 NUM eurjchem-32 87 52     SPACE eurjchem-32 87 53 ( ( PUNCT eurjchem-32 87 54 30.4 30.4 NUM eurjchem-32 87 55 ) ) PUNCT eurjchem-32 87 56 , , PUNCT eurjchem-32 87 57     SPACE eurjchem-32 87 58 93 93 NUM eurjchem-32 87 59     SPACE eurjchem-32 87 60 ( ( PUNCT eurjchem-32 87 61 95.7 95.7 NUM eurjchem-32 87 62 ) ) PUNCT eurjchem-32 87 63 , , PUNCT eurjchem-32 87 64     SPACE eurjchem-32 87 65 69 69 NUM eurjchem-32 87 66     SPACE eurjchem-32 87 67 ( ( PUNCT eurjchem-32 87 68 87.0 87.0 NUM eurjchem-32 87 69 ) ) PUNCT eurjchem-32 87 70 . . PUNCT eurjchem-32 87 71     SPACE eurjchem-32 88 1 anal anal ADJ eurjchem-32 88 2 . . PUNCT eurjchem-32 88 3     SPACE eurjchem-32 88 4 calcd calcd NOUN eurjchem-32 88 5 . . PUNCT eurjchem-32 88 6     SPACE eurjchem-32 89 1 for for ADP eurjchem-32 89 2     SPACE eurjchem-32 89 3 c12h7n3os2 c12h7n3os2 NOUN eurjchem-32 89 4 : : PUNCT eurjchem-32 89 5     SPACE eurjchem-32 89 6 c c X eurjchem-32 89 7 , , PUNCT eurjchem-32 89 8     SPACE eurjchem-32 89 9 52.73 52.73 NUM eurjchem-32 89 10 ; ; PUNCT eurjchem-32 89 11     SPACE eurjchem-32 89 12 h h NOUN eurjchem-32 89 13 , , PUNCT eurjchem-32 89 14     SPACE eurjchem-32 89 15 2.58 2.58 NUM eurjchem-32 89 16 ; ; PUNCT eurjchem-32 89 17     SPACE eurjchem-32 89 18 n n CCONJ eurjchem-32 89 19 , , PUNCT eurjchem-32 89 20     SPACE eurjchem-32 89 21 15.37 15.37 NUM eurjchem-32 89 22 . . PUNCT eurjchem-32 89 23     SPACE eurjchem-32 89 24 found find VERB eurjchem-32 89 25 : : PUNCT eurjchem-32 89 26     SPACE eurjchem-32 89 27 c c X eurjchem-32 89 28 , , PUNCT eurjchem-32 89 29     SPACE eurjchem-32 89 30 52.76 52.76 NUM eurjchem-32 89 31 ; ; PUNCT eurjchem-32 89 32     SPACE eurjchem-32 89 33 h h NOUN eurjchem-32 89 34 , , PUNCT eurjchem-32 89 35     SPACE eurjchem-32 89 36 2.61 2.61 NUM eurjchem-32 89 37 ; ; PUNCT eurjchem-32 89 38     SPACE eurjchem-32 89 39 n n CCONJ eurjchem-32 89 40 , , PUNCT eurjchem-32 89 41     SPACE eurjchem-32 89 42 15.45 15.45 NUM eurjchem-32 89 43 . . PUNCT eurjchem-32 89 44     SPACE eurjchem-32 89 45 scheme scheme NOUN eurjchem-32 89 46     SPACE eurjchem-32 89 47 13 13 NUM eurjchem-32 89 48         SPACE eurjchem-32 89 49 2.14 2.14 NUM eurjchem-32 89 50 . . PUNCT eurjchem-32 89 51     SPACE eurjchem-32 90 1 5­(benzo[d]thiazol­2­yl)­3­(benzo[d]thiazol­2­yl­ 5­(benzo[d]thiazol­2­yl)­3­(benzo[d]thiazol­2­yl­ NUM eurjchem-32 90 2 ( ( PUNCT eurjchem-32 90 3 cyanomethyl)­6­imino­4­oxo­4,5,6,7­tetrahydrothieno[2,3­ cyanomethyl)­6­imino­4­oxo­4,5,6,7­tetrahydrothieno[2,3­ NOUN eurjchem-32 90 4 b]pyridine­2­carbonitrile b]pyridine­2­carbonitrile NOUN eurjchem-32 90 5 , , PUNCT eurjchem-32 90 6     SPACE eurjchem-32 90 7 25 25 NUM eurjchem-32 90 8           SPACE eurjchem-32 90 9 a a DET eurjchem-32 90 10     SPACE eurjchem-32 90 11 mixture mixture NOUN eurjchem-32 90 12     SPACE eurjchem-32 90 13 of of ADP eurjchem-32 90 14     SPACE eurjchem-32 90 15 4 4 NUM eurjchem-32 90 16     SPACE eurjchem-32 90 17 ( ( PUNCT eurjchem-32 90 18 2.41 2.41 NUM eurjchem-32 90 19     SPACE eurjchem-32 90 20 g g NOUN eurjchem-32 90 21 , , PUNCT eurjchem-32 90 22     SPACE eurjchem-32 90 23 0.01 0.01 NUM eurjchem-32 90 24     SPACE eurjchem-32 90 25 mol mol NOUN eurjchem-32 90 26 ) ) PUNCT eurjchem-32 90 27 , , PUNCT eurjchem-32 90 28     SPACE eurjchem-32 90 29 orthorhombic orthorhombic NOUN eurjchem-32 90 30     SPACE eurjchem-32 90 31 sulfur sulfur NOUN eurjchem-32 90 32     SPACE eurjchem-32 90 33 ( ( PUNCT eurjchem-32 90 34 0.32 0.32 NUM eurjchem-32 90 35     SPACE eurjchem-32 90 36 g g NOUN eurjchem-32 90 37 , , PUNCT eurjchem-32 90 38     SPACE eurjchem-32 90 39 0.01 0.01 NUM eurjchem-32 90 40     SPACE eurjchem-32 90 41 mol mol NOUN eurjchem-32 90 42 ) ) PUNCT eurjchem-32 90 43 , , PUNCT eurjchem-32 90 44     SPACE eurjchem-32 90 45 morpholine morpholine NOUN eurjchem-32 90 46     SPACE eurjchem-32 90 47 ( ( PUNCT eurjchem-32 90 48 few few ADJ eurjchem-32 90 49     SPACE eurjchem-32 90 50 drops drop NOUN eurjchem-32 90 51 ) ) PUNCT eurjchem-32 90 52     SPACE eurjchem-32 90 53 and and CCONJ eurjchem-32 90 54     SPACE eurjchem-32 90 55 dmf dmf PROPN eurjchem-32 90 56     SPACE eurjchem-32 90 57 ( ( PUNCT eurjchem-32 90 58 3 3 NOUN eurjchem-32 90 59     SPACE eurjchem-32 90 60 ml ml NOUN eurjchem-32 90 61 ) ) PUNCT eurjchem-32 90 62     SPACE eurjchem-32 90 63 were be AUX eurjchem-32 90 64     SPACE eurjchem-32 90 65 kept keep VERB eurjchem-32 90 66     SPACE eurjchem-32 90 67 on on ADP eurjchem-32 90 68     SPACE eurjchem-32 90 69 a a DET eurjchem-32 90 70     SPACE eurjchem-32 90 71 water water NOUN eurjchem-32 90 72     SPACE eurjchem-32 90 73 bath bath NOUN eurjchem-32 90 74     SPACE eurjchem-32 90 75 at at ADP eurjchem-32 90 76     SPACE eurjchem-32 90 77 50‐60 50‐60 NUM eurjchem-32 90 78     SPACE eurjchem-32 90 79 oc oc NOUN eurjchem-32 90 80     SPACE eurjchem-32 90 81 for for ADP eurjchem-32 90 82     SPACE eurjchem-32 90 83 5 5 NUM eurjchem-32 90 84     SPACE eurjchem-32 90 85 h h NOUN eurjchem-32 90 86 , , PUNCT eurjchem-32 90 87     SPACE eurjchem-32 90 88 left leave VERB eurjchem-32 90 89     SPACE eurjchem-32 90 90 to to PART eurjchem-32 90 91     SPACE eurjchem-32 90 92 cool cool ADJ eurjchem-32 90 93 , , PUNCT eurjchem-32 90 94     SPACE eurjchem-32 90 95 poured pour VERB eurjchem-32 90 96     SPACE eurjchem-32 90 97 into into ADP eurjchem-32 90 98     SPACE eurjchem-32 90 99 ice ice NOUN eurjchem-32 90 100     SPACE eurjchem-32 90 101 cold cold ADJ eurjchem-32 90 102     SPACE eurjchem-32 90 103 water water NOUN eurjchem-32 90 104     SPACE eurjchem-32 90 105 and and CCONJ eurjchem-32 90 106     SPACE eurjchem-32 90 107 acidified acidify VERB eurjchem-32 90 108     SPACE eurjchem-32 90 109 by by ADP eurjchem-32 90 110     SPACE eurjchem-32 90 111 conc conc NOUN eurjchem-32 90 112 . . PUNCT eurjchem-32 90 113     SPACE eurjchem-32 91 1 hcl hcl PROPN eurjchem-32 91 2     SPACE eurjchem-32 91 3 ( ( PUNCT eurjchem-32 91 4 scheme scheme NOUN eurjchem-32 91 5     SPACE eurjchem-32 91 6 13 13 NUM eurjchem-32 91 7 ) ) PUNCT eurjchem-32 91 8 . . PUNCT eurjchem-32 91 9     SPACE eurjchem-32 92 1 the the DET eurjchem-32 92 2     SPACE eurjchem-32 92 3 formed form VERB eurjchem-32 92 4     SPACE eurjchem-32 92 5 solid solid NOUN eurjchem-32 92 6     SPACE eurjchem-32 92 7 was be AUX eurjchem-32 92 8     SPACE eurjchem-32 92 9 filtered filter VERB eurjchem-32 92 10     SPACE eurjchem-32 92 11 off off ADP eurjchem-32 92 12 , , PUNCT eurjchem-32 92 13     SPACE eurjchem-32 92 14 dried dry VERB eurjchem-32 92 15     SPACE eurjchem-32 92 16 and and CCONJ eurjchem-32 92 17     SPACE eurjchem-32 92 18 recrystallized recrystallize VERB eurjchem-32 92 19     SPACE eurjchem-32 92 20 from from ADP eurjchem-32 92 21     SPACE eurjchem-32 92 22 ethanol ethanol NOUN eurjchem-32 92 23     SPACE eurjchem-32 92 24 to to PART eurjchem-32 92 25     SPACE eurjchem-32 92 26 afford afford VERB eurjchem-32 92 27     SPACE eurjchem-32 92 28 3.58 3.58 NUM eurjchem-32 92 29     SPACE eurjchem-32 92 30 g g NOUN eurjchem-32 92 31     SPACE eurjchem-32 92 32 ( ( PUNCT eurjchem-32 92 33 72 72 NUM eurjchem-32 92 34 % % NOUN eurjchem-32 92 35 ) ) PUNCT eurjchem-32 92 36     SPACE eurjchem-32 92 37 of of ADP eurjchem-32 92 38     SPACE eurjchem-32 92 39 25 25 NUM eurjchem-32 92 40 ; ; PUNCT eurjchem-32 92 41     SPACE eurjchem-32 92 42 mp mp NOUN eurjchem-32 92 43     SPACE eurjchem-32 92 44 183 183 NUM eurjchem-32 92 45     SPACE eurjchem-32 92 46 oc oc NOUN eurjchem-32 92 47 ; ; PUNCT eurjchem-32 92 48     SPACE eurjchem-32 92 49 brown brown ADJ eurjchem-32 92 50     SPACE eurjchem-32 92 51 powder powder NOUN eurjchem-32 92 52 ; ; PUNCT eurjchem-32 92 53     SPACE eurjchem-32 92 54 ir ir PROPN eurjchem-32 92 55     SPACE eurjchem-32 92 56 ( ( PUNCT eurjchem-32 92 57 kbr kbr PROPN eurjchem-32 92 58 ) ) PUNCT eurjchem-32 92 59     SPACE eurjchem-32 92 60 ( ( PUNCT eurjchem-32 92 61 υ υ NOUN eurjchem-32 92 62 , , PUNCT eurjchem-32 92 63     SPACE eurjchem-32 92 64 cm‐1 cm‐1 NOUN eurjchem-32 92 65 ): ): PUNCT eurjchem-32 92 66     SPACE eurjchem-32 92 67 3220 3220 NUM eurjchem-32 92 68     SPACE eurjchem-32 92 69 ( ( PUNCT eurjchem-32 92 70 nh nh NOUN eurjchem-32 92 71 ) ) PUNCT eurjchem-32 92 72 , , PUNCT eurjchem-32 92 73     SPACE eurjchem-32 92 74 2195 2195 NUM eurjchem-32 92 75 , , PUNCT eurjchem-32 92 76     SPACE eurjchem-32 92 77 2220 2220 NUM eurjchem-32 92 78     SPACE eurjchem-32 92 79 ( ( PUNCT eurjchem-32 92 80 2cn 2cn ADJ eurjchem-32 92 81 ) ) PUNCT eurjchem-32 92 82 . . PUNCT eurjchem-32 92 83     SPACE eurjchem-32 93 1 1h 1h NUM eurjchem-32 93 2     SPACE eurjchem-32 93 3 nmr nmr NOUN eurjchem-32 93 4     SPACE eurjchem-32 93 5 ( ( PUNCT eurjchem-32 93 6 dmso‐d6 dmso‐d6 NOUN eurjchem-32 93 7 ): ): PUNCT eurjchem-32 93 8     SPACE eurjchem-32 93 9 δ δ PROPN eurjchem-32 93 10 , , PUNCT eurjchem-32 93 11     SPACE eurjchem-32 93 12 3.6 3.6 NUM eurjchem-32 93 13     SPACE eurjchem-32 93 14 ( ( PUNCT eurjchem-32 93 15 s s PROPN eurjchem-32 93 16 , , PUNCT eurjchem-32 93 17     SPACE eurjchem-32 93 18 1h 1h NUM eurjchem-32 93 19 , , PUNCT eurjchem-32 93 20     SPACE eurjchem-32 93 21 ch ch NOUN eurjchem-32 93 22 ) ) PUNCT eurjchem-32 93 23 , , PUNCT eurjchem-32 93 24     SPACE eurjchem-32 93 25 4.4 4.4 NUM eurjchem-32 93 26     SPACE eurjchem-32 93 27 ( ( PUNCT eurjchem-32 93 28 s s PROPN eurjchem-32 93 29 , , PUNCT eurjchem-32 93 30     SPACE eurjchem-32 93 31 1h 1h NUM eurjchem-32 93 32 , , PUNCT eurjchem-32 93 33     SPACE eurjchem-32 93 34 ch ch NOUN eurjchem-32 93 35 ) ) PUNCT eurjchem-32 93 36 , , PUNCT eurjchem-32 93 37     SPACE eurjchem-32 93 38 7.2‐8.1 7.2‐8.1 NUM eurjchem-32 93 39     SPACE eurjchem-32 93 40 ( ( PUNCT eurjchem-32 93 41 m m PROPN eurjchem-32 93 42 , , PUNCT eurjchem-32 93 43     SPACE eurjchem-32 93 44 8h 8h NUM eurjchem-32 93 45 , , PUNCT eurjchem-32 93 46     SPACE eurjchem-32 93 47 ar‐h ar‐h NOUN eurjchem-32 93 48 ) ) PUNCT eurjchem-32 93 49 , , PUNCT eurjchem-32 93 50     SPACE eurjchem-32 93 51 9.8 9.8 NUM eurjchem-32 93 52     SPACE eurjchem-32 93 53 ( ( PUNCT eurjchem-32 93 54 s s PROPN eurjchem-32 93 55 , , PUNCT eurjchem-32 93 56     SPACE eurjchem-32 93 57 1h 1h NUM eurjchem-32 93 58 , , PUNCT eurjchem-32 93 59     SPACE eurjchem-32 93 60 nh nh PROPN eurjchem-32 93 61 , , PUNCT eurjchem-32 93 62     SPACE eurjchem-32 93 63 cyclic cyclic NOUN eurjchem-32 93 64 ) ) PUNCT eurjchem-32 93 65 , , PUNCT eurjchem-32 93 66     SPACE eurjchem-32 93 67 13.7 13.7 NUM eurjchem-32 93 68     SPACE eurjchem-32 93 69 ( ( PUNCT eurjchem-32 93 70 bs bs PROPN eurjchem-32 93 71 , , PUNCT eurjchem-32 93 72     SPACE eurjchem-32 93 73 1h 1h NUM eurjchem-32 93 74 , , PUNCT eurjchem-32 93 75     SPACE eurjchem-32 93 76 nh nh PROPN eurjchem-32 93 77 ) ) PUNCT eurjchem-32 93 78 . . PUNCT eurjchem-32 93 79     SPACE eurjchem-32 94 1 ms ms NOUN eurjchem-32 94 2 : : PUNCT eurjchem-32 94 3     SPACE eurjchem-32 94 4 ( ( PUNCT eurjchem-32 94 5 m m PROPN eurjchem-32 94 6 / / SYM eurjchem-32 94 7 z z NOUN eurjchem-32 94 8 , , PUNCT eurjchem-32 94 9     SPACE eurjchem-32 94 10 % % NOUN eurjchem-32 94 11 ): ): PUNCT eurjchem-32 94 12     SPACE eurjchem-32 94 13 470 470 NUM eurjchem-32 94 14     SPACE eurjchem-32 94 15 ( ( PUNCT eurjchem-32 94 16 m+‐cn m+‐cn PROPN eurjchem-32 94 17 ) ) PUNCT eurjchem-32 94 18 , , PUNCT eurjchem-32 94 19     SPACE eurjchem-32 94 20 273 273 NUM eurjchem-32 94 21     SPACE eurjchem-32 94 22 ( ( PUNCT eurjchem-32 94 23 13.6 13.6 NUM eurjchem-32 94 24 ) ) PUNCT eurjchem-32 94 25 , , PUNCT eurjchem-32 94 26     SPACE eurjchem-32 94 27 241 241 NUM eurjchem-32 94 28     SPACE eurjchem-32 94 29 ( ( PUNCT eurjchem-32 94 30 31.3 31.3 NUM eurjchem-32 94 31 ) ) PUNCT eurjchem-32 94 32 , , PUNCT eurjchem-32 94 33     SPACE eurjchem-32 94 34 201 201 NUM eurjchem-32 94 35     SPACE eurjchem-32 94 36 ( ( PUNCT eurjchem-32 94 37 100.0 100.0 NUM eurjchem-32 94 38 ) ) PUNCT eurjchem-32 94 39 , , PUNCT eurjchem-32 94 40     SPACE eurjchem-32 94 41 146 146 NUM eurjchem-32 94 42     SPACE eurjchem-32 94 43 ( ( PUNCT eurjchem-32 94 44 30.2 30.2 NUM eurjchem-32 94 45 ) ) PUNCT eurjchem-32 94 46 , , PUNCT eurjchem-32 94 47     SPACE eurjchem-32 94 48 108 108 NUM eurjchem-32 94 49     SPACE eurjchem-32 94 50 ( ( PUNCT eurjchem-32 94 51 22.3 22.3 NUM eurjchem-32 94 52 ) ) PUNCT eurjchem-32 94 53 , , PUNCT eurjchem-32 94 54     SPACE eurjchem-32 94 55 69 69 NUM eurjchem-32 94 56     SPACE eurjchem-32 94 57 ( ( PUNCT eurjchem-32 94 58 38.9 38.9 NUM eurjchem-32 94 59 ) ) PUNCT eurjchem-32 94 60 . . PUNCT eurjchem-32 94 61     SPACE eurjchem-32 95 1 anal anal ADJ eurjchem-32 95 2 . . PUNCT eurjchem-32 95 3     SPACE eurjchem-32 95 4 calcd calcd NOUN eurjchem-32 95 5 . . PUNCT eurjchem-32 95 6     SPACE eurjchem-32 95 7 for for ADP eurjchem-32 95 8     SPACE eurjchem-32 95 9 c24h12n6os3 c24h12n6os3 NOUN eurjchem-32 95 10 : : PUNCT eurjchem-32 95 11     SPACE eurjchem-32 95 12 c c X eurjchem-32 95 13 , , PUNCT eurjchem-32 95 14     SPACE eurjchem-32 95 15 58.05 58.05 NUM eurjchem-32 95 16 ; ; PUNCT eurjchem-32 95 17     SPACE eurjchem-32 95 18 h h NOUN eurjchem-32 95 19 , , PUNCT eurjchem-32 95 20     SPACE eurjchem-32 95 21 2.44 2.44 NUM eurjchem-32 95 22 ; ; PUNCT eurjchem-32 95 23     SPACE eurjchem-32 95 24 n n CCONJ eurjchem-32 95 25 , , PUNCT eurjchem-32 95 26     SPACE eurjchem-32 95 27 16.92 16.92 NUM eurjchem-32 95 28 . . PUNCT eurjchem-32 95 29     SPACE eurjchem-32 95 30 found find VERB eurjchem-32 95 31 : : PUNCT eurjchem-32 95 32     SPACE eurjchem-32 95 33 c c X eurjchem-32 95 34 , , PUNCT eurjchem-32 95 35     SPACE eurjchem-32 95 36 58.14 58.14 NUM eurjchem-32 95 37 ; ; PUNCT eurjchem-32 95 38     SPACE eurjchem-32 95 39 h h NOUN eurjchem-32 95 40 , , PUNCT eurjchem-32 95 41     SPACE eurjchem-32 95 42 2.49 2.49 NUM eurjchem-32 95 43 ; ; PUNCT eurjchem-32 95 44     SPACE eurjchem-32 95 45 n n CCONJ eurjchem-32 95 46 , , PUNCT eurjchem-32 95 47     SPACE eurjchem-32 95 48 16.97 16.97 NUM eurjchem-32 95 49 . . PUNCT eurjchem-32 95 50         SPACE eurjchem-32 96 1 3 3 NUM eurjchem-32 96 2 . . PUNCT eurjchem-32 96 3     SPACE eurjchem-32 96 4 results result VERB eurjchem-32 96 5     SPACE eurjchem-32 96 6 and and CCONJ eurjchem-32 96 7     SPACE eurjchem-32 96 8 discussion discussion NOUN eurjchem-32 96 9         SPACE eurjchem-32 96 10 in in ADP eurjchem-32 96 11     SPACE eurjchem-32 96 12 continuation continuation NOUN eurjchem-32 96 13     SPACE eurjchem-32 96 14 of of ADP eurjchem-32 96 15     SPACE eurjchem-32 96 16 our our PRON eurjchem-32 96 17     SPACE eurjchem-32 96 18 program program NOUN eurjchem-32 96 19     SPACE eurjchem-32 96 20 and and CCONJ eurjchem-32 96 21     SPACE eurjchem-32 96 22 following follow VERB eurjchem-32 96 23     SPACE eurjchem-32 96 24 our our PRON eurjchem-32 96 25     SPACE eurjchem-32 96 26 previous previous ADJ eurjchem-32 96 27     SPACE eurjchem-32 96 28 interest interest NOUN eurjchem-32 96 29     SPACE eurjchem-32 97 1 [ [ X eurjchem-32 97 2 15‐20 15‐20 NUM eurjchem-32 97 3 ] ] PUNCT eurjchem-32 97 4     SPACE eurjchem-32 97 5 in in ADP eurjchem-32 97 6     SPACE eurjchem-32 97 7 the the DET eurjchem-32 97 8     SPACE eurjchem-32 97 9 synthesis synthesis NOUN eurjchem-32 97 10     SPACE eurjchem-32 97 11 of of ADP eurjchem-32 97 12     SPACE eurjchem-32 97 13 new new ADJ eurjchem-32 97 14     SPACE eurjchem-32 97 15 heterocyclic heterocyclic NOUN eurjchem-32 97 16     SPACE eurjchem-32 97 17 compounds compound NOUN eurjchem-32 97 18     SPACE eurjchem-32 97 19 of of ADP eurjchem-32 97 20     SPACE eurjchem-32 97 21 anticipated anticipated ADJ eurjchem-32 97 22     SPACE eurjchem-32 97 23 biological biological ADJ eurjchem-32 97 24     SPACE eurjchem-32 97 25 activity activity NOUN eurjchem-32 97 26 , , PUNCT eurjchem-32 97 27     SPACE eurjchem-32 97 28 it it PRON eurjchem-32 97 29     SPACE eurjchem-32 97 30 has have AUX eurjchem-32 97 31     SPACE eurjchem-32 97 32 been be AUX eurjchem-32 97 33     SPACE eurjchem-32 97 34 found find VERB eurjchem-32 97 35     SPACE eurjchem-32 97 36 that that SCONJ eurjchem-32 97 37     SPACE eurjchem-32 97 38 cyanoacetylation cyanoacetylation NOUN eurjchem-32 97 39     SPACE eurjchem-32 97 40 of of ADP eurjchem-32 97 41     SPACE eurjchem-32 97 42 2‐(benzo[d]thiazol‐2‐yl)acetonitrile 2‐(benzo[d]thiazol‐2‐yl)acetonitrile NOUN eurjchem-32 97 43 , , PUNCT eurjchem-32 97 44     SPACE eurjchem-32 97 45 3 3 NUM eurjchem-32 97 46 , , PUNCT eurjchem-32 97 47     SPACE eurjchem-32 97 48 will will AUX eurjchem-32 97 49     SPACE eurjchem-32 97 50 lead lead VERB eurjchem-32 97 51     SPACE eurjchem-32 97 52 to to ADP eurjchem-32 97 53     SPACE eurjchem-32 97 54 an an DET eurjchem-32 97 55     SPACE eurjchem-32 97 56 excellent excellent ADJ eurjchem-32 97 57     SPACE eurjchem-32 97 58 building building NOUN eurjchem-32 97 59     SPACE eurjchem-32 97 60 block block NOUN eurjchem-32 97 61     SPACE eurjchem-32 97 62 for for ADP eurjchem-32 97 63     SPACE eurjchem-32 97 64 the the DET eurjchem-32 97 65     SPACE eurjchem-32 97 66 synthesis synthesis NOUN eurjchem-32 97 67     SPACE eurjchem-32 97 68 of of ADP eurjchem-32 97 69     SPACE eurjchem-32 97 70 target target NOUN eurjchem-32 97 71     SPACE eurjchem-32 97 72 compounds compound NOUN eurjchem-32 97 73 . . PUNCT eurjchem-32 97 74     SPACE eurjchem-32 98 1 thus thus ADV eurjchem-32 98 2 , , PUNCT eurjchem-32 98 3     SPACE eurjchem-32 98 4 when when SCONJ eurjchem-32 98 5     SPACE eurjchem-32 98 6 3 3 NUM eurjchem-32 98 7     SPACE eurjchem-32 98 8 was be AUX eurjchem-32 98 9     SPACE eurjchem-32 98 10 treated treat VERB eurjchem-32 98 11     SPACE eurjchem-32 98 12 with with ADP eurjchem-32 98 13     SPACE eurjchem-32 98 14 cyanoacetic cyanoacetic ADJ eurjchem-32 98 15     SPACE eurjchem-32 98 16 acid acid NOUN eurjchem-32 98 17     SPACE eurjchem-32 98 18 in in ADP eurjchem-32 98 19     SPACE eurjchem-32 98 20 the the DET eurjchem-32 98 21     SPACE eurjchem-32 98 22 presence presence NOUN eurjchem-32 98 23     SPACE eurjchem-32 98 24 of of ADP eurjchem-32 98 25     SPACE eurjchem-32 98 26 acetic acetic ADJ eurjchem-32 98 27     SPACE eurjchem-32 98 28 anhydride anhydride NOUN eurjchem-32 98 29 , , PUNCT eurjchem-32 98 30     SPACE eurjchem-32 98 31 it it PRON eurjchem-32 98 32     SPACE eurjchem-32 98 33 afforded afford VERB eurjchem-32 98 34     SPACE eurjchem-32 98 35 the the DET eurjchem-32 98 36     SPACE eurjchem-32 98 37 corresponding corresponding ADJ eurjchem-32 98 38     SPACE eurjchem-32 98 39 2‐(benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile 2‐(benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile NUM eurjchem-32 98 40 , , PUNCT eurjchem-32 98 41     SPACE eurjchem-32 98 42 4 4 NUM eurjchem-32 98 43 , , PUNCT eurjchem-32 98 44     SPACE eurjchem-32 98 45 as as SCONJ eurjchem-32 98 46     SPACE eurjchem-32 98 47 tested test VERB eurjchem-32 98 48     SPACE eurjchem-32 98 49 by by ADP eurjchem-32 98 50     SPACE eurjchem-32 98 51 thin‐layer thin‐layer NOUN eurjchem-32 98 52     SPACE eurjchem-32 98 53 chromatography chromatography NOUN eurjchem-32 98 54     SPACE eurjchem-32 98 55 ( ( PUNCT eurjchem-32 98 56 tlc tlc NOUN eurjchem-32 98 57 ) ) PUNCT eurjchem-32 98 58     SPACE eurjchem-32 98 59 ( ( PUNCT eurjchem-32 98 60 scheme scheme NOUN eurjchem-32 98 61     SPACE eurjchem-32 98 62 2 2 NUM eurjchem-32 98 63 ) ) PUNCT eurjchem-32 98 64 . . PUNCT eurjchem-32 98 65     SPACE eurjchem-32 99 1 reactions reaction NOUN eurjchem-32 99 2     SPACE eurjchem-32 99 3 of of ADP eurjchem-32 99 4     SPACE eurjchem-32 99 5 this this DET eurjchem-32 99 6     SPACE eurjchem-32 99 7 type type NOUN eurjchem-32 99 8     SPACE eurjchem-32 99 9 have have AUX eurjchem-32 99 10     SPACE eurjchem-32 99 11 not not PART eurjchem-32 99 12     SPACE eurjchem-32 99 13 been be AUX eurjchem-32 99 14     SPACE eurjchem-32 99 15 previously previously ADV eurjchem-32 99 16     SPACE eurjchem-32 99 17 reported report VERB eurjchem-32 99 18 , , PUNCT eurjchem-32 99 19     SPACE eurjchem-32 99 20 however however ADV eurjchem-32 99 21     SPACE eurjchem-32 99 22 they they PRON eurjchem-32 99 23     SPACE eurjchem-32 99 24 were be AUX eurjchem-32 99 25     SPACE eurjchem-32 99 26 found find VERB eurjchem-32 99 27     SPACE eurjchem-32 99 28 to to PART eurjchem-32 99 29     SPACE eurjchem-32 99 30 give give VERB eurjchem-32 99 31     SPACE eurjchem-32 99 32 products product NOUN eurjchem-32 99 33     SPACE eurjchem-32 99 34 in in ADP eurjchem-32 99 35     SPACE eurjchem-32 99 36 excellent excellent ADJ eurjchem-32 99 37     SPACE eurjchem-32 99 38 yields yield NOUN eurjchem-32 99 39     SPACE eurjchem-32 99 40 under under ADP eurjchem-32 99 41     SPACE eurjchem-32 99 42 very very ADV eurjchem-32 99 43     SPACE eurjchem-32 99 44 mild mild ADJ eurjchem-32 99 45     SPACE eurjchem-32 99 46 conditions condition NOUN eurjchem-32 99 47 . . PUNCT eurjchem-32 99 48     SPACE eurjchem-32 100 1 moreover moreover ADV eurjchem-32 100 2 , , PUNCT eurjchem-32 100 3     SPACE eurjchem-32 100 4 the the DET eurjchem-32 100 5     SPACE eurjchem-32 100 6 resulting result VERB eurjchem-32 100 7     SPACE eurjchem-32 100 8 benzothiazole benzothiazole NOUN eurjchem-32 100 9     SPACE eurjchem-32 100 10 derivative derivative NOUN eurjchem-32 100 11     SPACE eurjchem-32 100 12 4 4 NUM eurjchem-32 100 13     SPACE eurjchem-32 100 14 has have VERB eurjchem-32 100 15     SPACE eurjchem-32 100 16 latent latent NOUN eurjchem-32 100 17     SPACE eurjchem-32 100 18 functional functional ADJ eurjchem-32 100 19     SPACE eurjchem-32 100 20 substituents substituent NOUN eurjchem-32 100 21 , , PUNCT eurjchem-32 100 22     SPACE eurjchem-32 100 23 which which PRON eurjchem-32 100 24     SPACE eurjchem-32 100 25 render render VERB eurjchem-32 100 26     SPACE eurjchem-32 100 27 it it PRON eurjchem-32 100 28     SPACE eurjchem-32 100 29 to to PART eurjchem-32 100 30     SPACE eurjchem-32 100 31 be be AUX eurjchem-32 100 32     SPACE eurjchem-32 100 33 a a DET eurjchem-32 100 34     SPACE eurjchem-32 100 35 versatile versatile ADJ eurjchem-32 100 36     SPACE eurjchem-32 100 37 starting starting NOUN eurjchem-32 100 38     SPACE eurjchem-32 100 39 substrate substrate NOUN eurjchem-32 100 40     SPACE eurjchem-32 100 41 for for ADP eurjchem-32 100 42     SPACE eurjchem-32 100 43 further further ADJ eurjchem-32 100 44     SPACE eurjchem-32 100 45 chemical chemical NOUN eurjchem-32 100 46     SPACE eurjchem-32 100 47 transformations transformation NOUN eurjchem-32 100 48     SPACE eurjchem-32 100 49 that that PRON eurjchem-32 100 50     SPACE eurjchem-32 100 51 open open VERB eurjchem-32 100 52     SPACE eurjchem-32 100 53 new new ADJ eurjchem-32 100 54     SPACE eurjchem-32 100 55 routes route NOUN eurjchem-32 100 56     SPACE eurjchem-32 100 57 for for ADP eurjchem-32 100 58     SPACE eurjchem-32 100 59 the the DET eurjchem-32 100 60     SPACE eurjchem-32 100 61 94 94 NUM eurjchem-32 100 62     SPACE eurjchem-32 100 63 fadda fadda NOUN eurjchem-32 100 64     SPACE eurjchem-32 100 65 et et PROPN eurjchem-32 100 66     SPACE eurjchem-32 100 67 al al PROPN eurjchem-32 100 68 . . PROPN eurjchem-32 100 69     SPACE eurjchem-32 100 70 / / SYM eurjchem-32 100 71     SPACE eurjchem-32 100 72 european european ADJ eurjchem-32 100 73     SPACE eurjchem-32 100 74 journal journal NOUN eurjchem-32 100 75     SPACE eurjchem-32 100 76 of of ADP eurjchem-32 100 77     SPACE eurjchem-32 100 78 chemistry chemistry NOUN eurjchem-32 100 79     SPACE eurjchem-32 100 80 1 1 NUM eurjchem-32 100 81     SPACE eurjchem-32 100 82 ( ( PUNCT eurjchem-32 100 83 2 2 NUM eurjchem-32 100 84 ) ) PUNCT eurjchem-32 100 85     SPACE eurjchem-32 100 86 ( ( PUNCT eurjchem-32 100 87 2010 2010 NUM eurjchem-32 100 88 ) ) PUNCT eurjchem-32 100 89     SPACE eurjchem-32 100 90 90­95 90­95 NUM eurjchem-32 100 91         SPACE eurjchem-32 100 92 preparation preparation NOUN eurjchem-32 100 93     SPACE eurjchem-32 100 94 of of ADP eurjchem-32 100 95     SPACE eurjchem-32 100 96 substituted substitute VERB eurjchem-32 100 97     SPACE eurjchem-32 100 98 benzothiazole benzothiazole NOUN eurjchem-32 100 99     SPACE eurjchem-32 100 100 derivatives derivative NOUN eurjchem-32 100 101     SPACE eurjchem-32 100 102 with with ADP eurjchem-32 100 103     SPACE eurjchem-32 100 104 possible possible ADJ eurjchem-32 100 105     SPACE eurjchem-32 100 106 biological biological ADJ eurjchem-32 100 107     SPACE eurjchem-32 100 108 activity activity NOUN eurjchem-32 100 109 . . PUNCT eurjchem-32 100 110     SPACE eurjchem-32 101 1 its its PRON eurjchem-32 101 2     SPACE eurjchem-32 101 3 structural structural ADJ eurjchem-32 101 4     SPACE eurjchem-32 101 5 assignment assignment NOUN eurjchem-32 101 6     SPACE eurjchem-32 101 7 was be AUX eurjchem-32 101 8     SPACE eurjchem-32 101 9 proved prove VERB eurjchem-32 101 10     SPACE eurjchem-32 101 11 by by ADP eurjchem-32 101 12     SPACE eurjchem-32 101 13 spectroscopic spectroscopic NOUN eurjchem-32 101 14     SPACE eurjchem-32 101 15 analyses analysis NOUN eurjchem-32 101 16 . . PUNCT eurjchem-32 101 17     SPACE eurjchem-32 102 1 the the DET eurjchem-32 102 2     SPACE eurjchem-32 102 3 ir ir NOUN eurjchem-32 102 4     SPACE eurjchem-32 102 5 spectrum spectrum NOUN eurjchem-32 102 6     SPACE eurjchem-32 102 7 of of ADP eurjchem-32 102 8     SPACE eurjchem-32 102 9 the the DET eurjchem-32 102 10     SPACE eurjchem-32 102 11 latter latter ADJ eurjchem-32 102 12     SPACE eurjchem-32 102 13 product product NOUN eurjchem-32 102 14     SPACE eurjchem-32 102 15 revealed reveal VERB eurjchem-32 102 16     SPACE eurjchem-32 102 17 absorption absorption NOUN eurjchem-32 102 18     SPACE eurjchem-32 102 19 bands band NOUN eurjchem-32 102 20     SPACE eurjchem-32 102 21 at at ADP eurjchem-32 102 22     SPACE eurjchem-32 102 23 2185 2185 NUM eurjchem-32 102 24 , , PUNCT eurjchem-32 102 25     SPACE eurjchem-32 102 26 2199 2199 NUM eurjchem-32 102 27     SPACE eurjchem-32 102 28 cm‐1 cm‐1 NOUN eurjchem-32 102 29     SPACE eurjchem-32 102 30 due due ADJ eurjchem-32 102 31     SPACE eurjchem-32 102 32 to to ADP eurjchem-32 102 33     SPACE eurjchem-32 102 34 two two NUM eurjchem-32 102 35     SPACE eurjchem-32 102 36 cn cn PROPN eurjchem-32 102 37     SPACE eurjchem-32 102 38 groups group NOUN eurjchem-32 102 39 , , PUNCT eurjchem-32 102 40     SPACE eurjchem-32 102 41 a a DET eurjchem-32 102 42     SPACE eurjchem-32 102 43 very very ADV eurjchem-32 102 44     SPACE eurjchem-32 102 45 weak weak ADJ eurjchem-32 102 46     SPACE eurjchem-32 102 47 band band NOUN eurjchem-32 102 48     SPACE eurjchem-32 102 49 near near ADP eurjchem-32 102 50     SPACE eurjchem-32 102 51 1700 1700 NUM eurjchem-32 102 52     SPACE eurjchem-32 102 53 cm‐1 cm‐1 NOUN eurjchem-32 102 54     SPACE eurjchem-32 102 55 that that PRON eurjchem-32 102 56     SPACE eurjchem-32 102 57 was be AUX eurjchem-32 102 58     SPACE eurjchem-32 102 59 attributed attribute VERB eurjchem-32 102 60     SPACE eurjchem-32 102 61 to to ADP eurjchem-32 102 62     SPACE eurjchem-32 102 63 the the DET eurjchem-32 102 64     SPACE eurjchem-32 102 65 carbonyl carbonyl NOUN eurjchem-32 102 66     SPACE eurjchem-32 102 67 group group NOUN eurjchem-32 102 68 . . PUNCT eurjchem-32 102 69     SPACE eurjchem-32 103 1 its its PRON eurjchem-32 103 2     SPACE eurjchem-32 103 3 1h 1h NUM eurjchem-32 103 4     SPACE eurjchem-32 103 5 nmr nmr NOUN eurjchem-32 103 6     SPACE eurjchem-32 103 7 spectrum spectrum NOUN eurjchem-32 103 8     SPACE eurjchem-32 103 9 revealed reveal VERB eurjchem-32 103 10     SPACE eurjchem-32 103 11 singlet singlet NOUN eurjchem-32 103 12     SPACE eurjchem-32 103 13 signals signal NOUN eurjchem-32 103 14     SPACE eurjchem-32 103 15 at at ADP eurjchem-32 103 16     SPACE eurjchem-32 103 17 δ δ PROPN eurjchem-32 103 18     SPACE eurjchem-32 103 19 4.52 4.52 NUM eurjchem-32 103 20     SPACE eurjchem-32 103 21 and and CCONJ eurjchem-32 103 22     SPACE eurjchem-32 103 23 5.10 5.10 NUM eurjchem-32 103 24     SPACE eurjchem-32 103 25 ppm ppm NOUN eurjchem-32 103 26     SPACE eurjchem-32 103 27 due due ADJ eurjchem-32 103 28     SPACE eurjchem-32 103 29 to to ADP eurjchem-32 103 30     SPACE eurjchem-32 103 31 ch2 ch2 PROPN eurjchem-32 103 32     SPACE eurjchem-32 103 33 and and CCONJ eurjchem-32 103 34     SPACE eurjchem-32 103 35 ch ch NOUN eurjchem-32 103 36     SPACE eurjchem-32 103 37 proton proton NOUN eurjchem-32 103 38 , , PUNCT eurjchem-32 103 39     SPACE eurjchem-32 103 40 respectively respectively ADV eurjchem-32 103 41 , , PUNCT eurjchem-32 103 42     SPACE eurjchem-32 103 43 beside beside ADP eurjchem-32 103 44     SPACE eurjchem-32 103 45 an an DET eurjchem-32 103 46     SPACE eurjchem-32 103 47 aromatic aromatic ADJ eurjchem-32 103 48     SPACE eurjchem-32 103 49 multiplet multiplet NOUN eurjchem-32 103 50     SPACE eurjchem-32 103 51 in in ADP eurjchem-32 103 52     SPACE eurjchem-32 103 53 the the DET eurjchem-32 103 54     SPACE eurjchem-32 103 55 region region NOUN eurjchem-32 103 56     SPACE eurjchem-32 103 57 of of ADP eurjchem-32 103 58     SPACE eurjchem-32 103 59 δ δ PROPN eurjchem-32 103 60     SPACE eurjchem-32 103 61 6.67‐7.5 6.67‐7.5 NOUN eurjchem-32 103 62     SPACE eurjchem-32 103 63 ppm ppm NOUN eurjchem-32 103 64 . . PUNCT eurjchem-32 103 65     SPACE eurjchem-32 104 1 moreover moreover ADV eurjchem-32 104 2 , , PUNCT eurjchem-32 104 3     SPACE eurjchem-32 104 4 the the DET eurjchem-32 104 5     SPACE eurjchem-32 104 6 mass mass NOUN eurjchem-32 104 7     SPACE eurjchem-32 104 8 spectrum spectrum NOUN eurjchem-32 104 9     SPACE eurjchem-32 104 10 showed show VERB eurjchem-32 104 11     SPACE eurjchem-32 104 12 m m PROPN eurjchem-32 104 13 / / PROPN eurjchem-32 104 14 z z NOUN eurjchem-32 104 15     SPACE eurjchem-32 104 16 at at ADP eurjchem-32 104 17     SPACE eurjchem-32 104 18 241(m+ 241(m+ NOUN eurjchem-32 104 19 ) ) PUNCT eurjchem-32 104 20 , , PUNCT eurjchem-32 104 21     SPACE eurjchem-32 104 22 201[m+‐ 201[m+‐ PROPN eurjchem-32 104 23 ch2cn ch2cn VERB eurjchem-32 104 24 ] ] X eurjchem-32 104 25     SPACE eurjchem-32 104 26 ( ( PUNCT eurjchem-32 104 27 100 100 NUM eurjchem-32 104 28 % % NOUN eurjchem-32 104 29 ) ) PUNCT eurjchem-32 104 30 , , PUNCT eurjchem-32 104 31     SPACE eurjchem-32 104 32 173 173 NUM eurjchem-32 104 33     SPACE eurjchem-32 105 1 [ [ X eurjchem-32 105 2 m+‐coch2cn m+‐coch2cn PROPN eurjchem-32 105 3 ] ] X eurjchem-32 105 4     SPACE eurjchem-32 105 5 ( ( PUNCT eurjchem-32 105 6 20.8 20.8 NUM eurjchem-32 105 7 % % NOUN eurjchem-32 105 8 ) ) PUNCT eurjchem-32 105 9 . . PUNCT eurjchem-32 105 10     SPACE eurjchem-32 106 1 now now ADV eurjchem-32 106 2 , , PUNCT eurjchem-32 106 3     SPACE eurjchem-32 106 4 we we PRON eurjchem-32 106 5     SPACE eurjchem-32 106 6 have have AUX eurjchem-32 106 7     SPACE eurjchem-32 106 8 extended extend VERB eurjchem-32 106 9     SPACE eurjchem-32 106 10 our our PRON eurjchem-32 106 11     SPACE eurjchem-32 106 12 synthetic synthetic ADJ eurjchem-32 106 13     SPACE eurjchem-32 106 14 program program NOUN eurjchem-32 106 15     SPACE eurjchem-32 106 16 to to ADP eurjchem-32 106 17     SPACE eurjchem-32 106 18 the the DET eurjchem-32 106 19     SPACE eurjchem-32 106 20 synthesis synthesis NOUN eurjchem-32 106 21     SPACE eurjchem-32 106 22 of of ADP eurjchem-32 106 23     SPACE eurjchem-32 106 24 otherwise otherwise ADV eurjchem-32 106 25     SPACE eurjchem-32 106 26 inaccessible inaccessible ADJ eurjchem-32 106 27     SPACE eurjchem-32 106 28 heterocyclic heterocyclic NOUN eurjchem-32 106 29     SPACE eurjchem-32 106 30 ring ring NOUN eurjchem-32 106 31     SPACE eurjchem-32 106 32 system system NOUN eurjchem-32 106 33     SPACE eurjchem-32 106 34 utilizing utilize VERB eurjchem-32 106 35     SPACE eurjchem-32 106 36 compound compound NOUN eurjchem-32 106 37     SPACE eurjchem-32 106 38 4 4 NUM eurjchem-32 106 39     SPACE eurjchem-32 106 40 as as ADP eurjchem-32 106 41     SPACE eurjchem-32 106 42 the the DET eurjchem-32 106 43     SPACE eurjchem-32 106 44 key key NOUN eurjchem-32 106 45     SPACE eurjchem-32 106 46 starting starting NOUN eurjchem-32 106 47     SPACE eurjchem-32 106 48 material material NOUN eurjchem-32 106 49 . . PUNCT eurjchem-32 106 50     SPACE eurjchem-32 107 1 a a DET eurjchem-32 107 2     SPACE eurjchem-32 107 3 mixture mixture NOUN eurjchem-32 107 4     SPACE eurjchem-32 107 5 of of ADP eurjchem-32 107 6     SPACE eurjchem-32 107 7 4 4 NUM eurjchem-32 107 8     SPACE eurjchem-32 107 9 and and CCONJ eurjchem-32 107 10     SPACE eurjchem-32 107 11 p‐chlorobenzaldehyde p‐chlorobenzaldehyde VERB eurjchem-32 107 12     SPACE eurjchem-32 107 13 reacted react VERB eurjchem-32 107 14     SPACE eurjchem-32 107 15 in in ADP eurjchem-32 107 16     SPACE eurjchem-32 107 17 refluxing refluxing NOUN eurjchem-32 107 18     SPACE eurjchem-32 107 19 ethanol ethanol NOUN eurjchem-32 107 20     SPACE eurjchem-32 107 21 in in ADP eurjchem-32 107 22     SPACE eurjchem-32 107 23 the the DET eurjchem-32 107 24     SPACE eurjchem-32 107 25 presence presence NOUN eurjchem-32 107 26     SPACE eurjchem-32 107 27 of of ADP eurjchem-32 107 28     SPACE eurjchem-32 107 29 catalytic catalytic ADJ eurjchem-32 107 30     SPACE eurjchem-32 107 31 amounts amount NOUN eurjchem-32 107 32     SPACE eurjchem-32 107 33 of of ADP eurjchem-32 107 34     SPACE eurjchem-32 107 35 piperidine piperidine NOUN eurjchem-32 107 36     SPACE eurjchem-32 107 37 to to PART eurjchem-32 107 38     SPACE eurjchem-32 107 39 yield yield VERB eurjchem-32 107 40     SPACE eurjchem-32 107 41 a a DET eurjchem-32 107 42     SPACE eurjchem-32 107 43 product product NOUN eurjchem-32 107 44     SPACE eurjchem-32 107 45 which which PRON eurjchem-32 107 46     SPACE eurjchem-32 107 47 may may AUX eurjchem-32 107 48     SPACE eurjchem-32 107 49 be be AUX eurjchem-32 107 50     SPACE eurjchem-32 107 51 formulated formulate VERB eurjchem-32 107 52     SPACE eurjchem-32 107 53 as as ADP eurjchem-32 107 54     SPACE eurjchem-32 107 55 5 5 NUM eurjchem-32 107 56     SPACE eurjchem-32 107 57 or or CCONJ eurjchem-32 107 58     SPACE eurjchem-32 107 59 6 6 NUM eurjchem-32 107 60     SPACE eurjchem-32 107 61 ( ( PUNCT eurjchem-32 107 62 scheme scheme NOUN eurjchem-32 107 63     SPACE eurjchem-32 107 64 3 3 NUM eurjchem-32 107 65 ) ) PUNCT eurjchem-32 107 66 . . PUNCT eurjchem-32 107 67     SPACE eurjchem-32 108 1 structure structure NOUN eurjchem-32 108 2     SPACE eurjchem-32 108 3 6 6 NUM eurjchem-32 108 4     SPACE eurjchem-32 108 5 was be AUX eurjchem-32 108 6     SPACE eurjchem-32 108 7 ruled rule VERB eurjchem-32 108 8     SPACE eurjchem-32 108 9 out out ADP eurjchem-32 108 10     SPACE eurjchem-32 108 11 on on ADP eurjchem-32 108 12     SPACE eurjchem-32 108 13 the the DET eurjchem-32 108 14     SPACE eurjchem-32 108 15 basis basis NOUN eurjchem-32 108 16     SPACE eurjchem-32 108 17 of of ADP eurjchem-32 108 18     SPACE eurjchem-32 108 19 1h 1h NUM eurjchem-32 108 20     SPACE eurjchem-32 108 21 nmr nmr NOUN eurjchem-32 108 22     SPACE eurjchem-32 108 23 spectrum spectrum NOUN eurjchem-32 108 24     SPACE eurjchem-32 108 25 of of ADP eurjchem-32 108 26     SPACE eurjchem-32 108 27 the the DET eurjchem-32 108 28     SPACE eurjchem-32 108 29 reaction reaction NOUN eurjchem-32 108 30     SPACE eurjchem-32 108 31 product product NOUN eurjchem-32 108 32 , , PUNCT eurjchem-32 108 33     SPACE eurjchem-32 108 34 which which PRON eurjchem-32 108 35     SPACE eurjchem-32 108 36 revealed reveal VERB eurjchem-32 108 37     SPACE eurjchem-32 108 38 a a DET eurjchem-32 108 39     SPACE eurjchem-32 108 40 multiplet multiplet NOUN eurjchem-32 108 41     SPACE eurjchem-32 108 42 at at ADP eurjchem-32 108 43     SPACE eurjchem-32 108 44 δ δ PROPN eurjchem-32 108 45     SPACE eurjchem-32 108 46 7.32‐8.12 7.32‐8.12 PROPN eurjchem-32 108 47     SPACE eurjchem-32 108 48 ppm ppm NOUN eurjchem-32 108 49     SPACE eurjchem-32 108 50 due due ADJ eurjchem-32 108 51     SPACE eurjchem-32 108 52 to to ADP eurjchem-32 108 53     SPACE eurjchem-32 108 54 the the DET eurjchem-32 108 55     SPACE eurjchem-32 108 56 aromatic aromatic NOUN eurjchem-32 108 57     SPACE eurjchem-32 108 58 and and CCONJ eurjchem-32 108 59     SPACE eurjchem-32 108 60 the the DET eurjchem-32 108 61     SPACE eurjchem-32 108 62 vinylic vinylic ADJ eurjchem-32 108 63     SPACE eurjchem-32 108 64 proton proton NOUN eurjchem-32 108 65     SPACE eurjchem-32 108 66 being be AUX eurjchem-32 108 67     SPACE eurjchem-32 108 68 embedded embed VERB eurjchem-32 108 69     SPACE eurjchem-32 108 70 in in ADP eurjchem-32 108 71 . . PUNCT eurjchem-32 108 72     SPACE eurjchem-32 108 73 in in ADP eurjchem-32 108 74     SPACE eurjchem-32 108 75 addition addition NOUN eurjchem-32 108 76 , , PUNCT eurjchem-32 108 77     SPACE eurjchem-32 108 78 the the DET eurjchem-32 108 79     SPACE eurjchem-32 108 80 ir ir NOUN eurjchem-32 108 81     SPACE eurjchem-32 108 82 spectrum spectrum NOUN eurjchem-32 108 83     SPACE eurjchem-32 108 84 showed show VERB eurjchem-32 108 85     SPACE eurjchem-32 108 86 absorption absorption NOUN eurjchem-32 108 87     SPACE eurjchem-32 108 88 bands band NOUN eurjchem-32 108 89     SPACE eurjchem-32 108 90 at at ADP eurjchem-32 108 91     SPACE eurjchem-32 108 92 2188 2188 NUM eurjchem-32 108 93     SPACE eurjchem-32 108 94 cm‐1 cm‐1 NOUN eurjchem-32 108 95     SPACE eurjchem-32 108 96 due due ADJ eurjchem-32 108 97     SPACE eurjchem-32 108 98 to to ADP eurjchem-32 108 99     SPACE eurjchem-32 108 100 the the DET eurjchem-32 108 101     SPACE eurjchem-32 108 102 cn cn PROPN eurjchem-32 108 103     SPACE eurjchem-32 108 104 group group NOUN eurjchem-32 108 105 , , PUNCT eurjchem-32 108 106     SPACE eurjchem-32 108 107 indicating indicate VERB eurjchem-32 108 108     SPACE eurjchem-32 108 109 the the DET eurjchem-32 108 110     SPACE eurjchem-32 108 111 presence presence NOUN eurjchem-32 108 112     SPACE eurjchem-32 108 113 of of ADP eurjchem-32 108 114     SPACE eurjchem-32 108 115 one one NUM eurjchem-32 108 116     SPACE eurjchem-32 108 117 cyano cyano NOUN eurjchem-32 108 118     SPACE eurjchem-32 108 119 group group NOUN eurjchem-32 108 120     SPACE eurjchem-32 108 121 and and CCONJ eurjchem-32 108 122     SPACE eurjchem-32 108 123 the the DET eurjchem-32 108 124     SPACE eurjchem-32 108 125 absence absence NOUN eurjchem-32 108 126     SPACE eurjchem-32 108 127 of of ADP eurjchem-32 108 128     SPACE eurjchem-32 108 129 any any DET eurjchem-32 108 130     SPACE eurjchem-32 108 131 bands band NOUN eurjchem-32 108 132     SPACE eurjchem-32 108 133 in in ADP eurjchem-32 108 134     SPACE eurjchem-32 108 135 the the DET eurjchem-32 108 136     SPACE eurjchem-32 108 137 region region NOUN eurjchem-32 108 138     SPACE eurjchem-32 108 139 of of ADP eurjchem-32 108 140     SPACE eurjchem-32 108 141 co co NOUN eurjchem-32 108 142     SPACE eurjchem-32 108 143 group group NOUN eurjchem-32 108 144     SPACE eurjchem-32 108 145 absorption absorption NOUN eurjchem-32 108 146 . . PUNCT eurjchem-32 108 147     SPACE eurjchem-32 109 1 the the DET eurjchem-32 109 2     SPACE eurjchem-32 109 3 mass mass ADJ eurjchem-32 109 4     SPACE eurjchem-32 109 5 spectroscopic spectroscopic NOUN eurjchem-32 109 6     SPACE eurjchem-32 109 7 measurements measurement NOUN eurjchem-32 109 8     SPACE eurjchem-32 109 9 showed show VERB eurjchem-32 109 10     SPACE eurjchem-32 109 11 m m PROPN eurjchem-32 109 12 / / PROPN eurjchem-32 109 13 z z NOUN eurjchem-32 109 14     SPACE eurjchem-32 109 15 297 297 NUM eurjchem-32 109 16     SPACE eurjchem-32 109 17 ( ( PUNCT eurjchem-32 109 18 m+ m+ NOUN eurjchem-32 109 19 ) ) PUNCT eurjchem-32 109 20     SPACE eurjchem-32 109 21 which which PRON eurjchem-32 109 22     SPACE eurjchem-32 109 23 indicates indicate VERB eurjchem-32 109 24     SPACE eurjchem-32 109 25 structure structure NOUN eurjchem-32 109 26     SPACE eurjchem-32 109 27 5 5 NUM eurjchem-32 109 28 . . PUNCT eurjchem-32 109 29     SPACE eurjchem-32 109 30 the the DET eurjchem-32 109 31     SPACE eurjchem-32 109 32 structure structure NOUN eurjchem-32 109 33     SPACE eurjchem-32 109 34 of of ADP eurjchem-32 109 35     SPACE eurjchem-32 109 36 5 5 NUM eurjchem-32 109 37     SPACE eurjchem-32 109 38 was be AUX eurjchem-32 109 39     SPACE eurjchem-32 109 40 further far ADV eurjchem-32 109 41     SPACE eurjchem-32 109 42 confirmed confirm VERB eurjchem-32 109 43     SPACE eurjchem-32 109 44 by by ADP eurjchem-32 109 45     SPACE eurjchem-32 109 46 an an DET eurjchem-32 109 47     SPACE eurjchem-32 109 48 alternative alternative ADJ eurjchem-32 109 49     SPACE eurjchem-32 109 50 synthesis synthesis NOUN eurjchem-32 109 51 . . PUNCT eurjchem-32 109 52     SPACE eurjchem-32 110 1 the the DET eurjchem-32 110 2     SPACE eurjchem-32 110 3 treatment treatment NOUN eurjchem-32 110 4     SPACE eurjchem-32 110 5 of of ADP eurjchem-32 110 6     SPACE eurjchem-32 110 7 3 3 NUM eurjchem-32 110 8     SPACE eurjchem-32 110 9 with with ADP eurjchem-32 110 10     SPACE eurjchem-32 110 11 p‐chlorobenzaldehyde p‐chlorobenzaldehyde NOUN eurjchem-32 110 12     SPACE eurjchem-32 110 13 in in ADP eurjchem-32 110 14     SPACE eurjchem-32 110 15 refluxing refluxing NOUN eurjchem-32 110 16     SPACE eurjchem-32 110 17 ethanol ethanol NOUN eurjchem-32 110 18     SPACE eurjchem-32 110 19 in in ADP eurjchem-32 110 20     SPACE eurjchem-32 110 21 the the DET eurjchem-32 110 22     SPACE eurjchem-32 110 23 presence presence NOUN eurjchem-32 110 24     SPACE eurjchem-32 110 25 of of ADP eurjchem-32 110 26     SPACE eurjchem-32 110 27 piperidine piperidine NOUN eurjchem-32 110 28     SPACE eurjchem-32 110 29 ( ( PUNCT eurjchem-32 110 30 catalytic catalytic NOUN eurjchem-32 110 31     SPACE eurjchem-32 110 32 amounts amount NOUN eurjchem-32 110 33 ) ) PUNCT eurjchem-32 110 34     SPACE eurjchem-32 110 35 yielded yield VERB eurjchem-32 110 36     SPACE eurjchem-32 110 37 a a DET eurjchem-32 110 38     SPACE eurjchem-32 110 39 product product NOUN eurjchem-32 110 40     SPACE eurjchem-32 110 41 completely completely ADV eurjchem-32 110 42     SPACE eurjchem-32 110 43 identical identical ADJ eurjchem-32 110 44     SPACE eurjchem-32 110 45 in in ADP eurjchem-32 110 46     SPACE eurjchem-32 110 47 all all DET eurjchem-32 110 48     SPACE eurjchem-32 110 49 respects respect VERB eurjchem-32 110 50     SPACE eurjchem-32 110 51 ( ( PUNCT eurjchem-32 110 52 m.p m.p PROPN eurjchem-32 110 53 . . PROPN eurjchem-32 110 54 , , PUNCT eurjchem-32 110 55     SPACE eurjchem-32 110 56 mixed mix VERB eurjchem-32 110 57     SPACE eurjchem-32 110 58 m.p m.p PROPN eurjchem-32 110 59 . . PROPN eurjchem-32 110 60 , , PUNCT eurjchem-32 110 61     SPACE eurjchem-32 110 62 ir ir VERB eurjchem-32 110 63     SPACE eurjchem-32 110 64 and and CCONJ eurjchem-32 110 65     SPACE eurjchem-32 110 66 1h 1h NUM eurjchem-32 110 67     SPACE eurjchem-32 110 68 nmr nmr NOUN eurjchem-32 110 69 ) ) PUNCT eurjchem-32 110 70     SPACE eurjchem-32 110 71 with with ADP eurjchem-32 110 72     SPACE eurjchem-32 110 73 5 5 NUM eurjchem-32 110 74 . . PUNCT eurjchem-32 110 75     SPACE eurjchem-32 110 76 pyrimidine pyrimidine NOUN eurjchem-32 110 77     SPACE eurjchem-32 110 78 is be AUX eurjchem-32 110 79     SPACE eurjchem-32 110 80 the the DET eurjchem-32 110 81     SPACE eurjchem-32 110 82 parent parent NOUN eurjchem-32 110 83     SPACE eurjchem-32 110 84 hetero hetero NOUN eurjchem-32 110 85     SPACE eurjchem-32 110 86 ring ring NOUN eurjchem-32 110 87     SPACE eurjchem-32 110 88 of of ADP eurjchem-32 110 89     SPACE eurjchem-32 110 90 a a DET eurjchem-32 110 91     SPACE eurjchem-32 110 92 very very ADV eurjchem-32 110 93     SPACE eurjchem-32 110 94 important important ADJ eurjchem-32 110 95     SPACE eurjchem-32 110 96 group group NOUN eurjchem-32 110 97     SPACE eurjchem-32 110 98 of of ADP eurjchem-32 110 99     SPACE eurjchem-32 110 100 compounds compound NOUN eurjchem-32 110 101     SPACE eurjchem-32 110 102 that that PRON eurjchem-32 110 103     SPACE eurjchem-32 110 104 are be AUX eurjchem-32 110 105     SPACE eurjchem-32 110 106 extensively extensively ADV eurjchem-32 110 107     SPACE eurjchem-32 110 108 studied study VERB eurjchem-32 110 109     SPACE eurjchem-32 110 110 due due ADJ eurjchem-32 110 111     SPACE eurjchem-32 110 112 to to ADP eurjchem-32 110 113     SPACE eurjchem-32 110 114 their their PRON eurjchem-32 110 115     SPACE eurjchem-32 110 116 occurrence occurrence NOUN eurjchem-32 110 117     SPACE eurjchem-32 110 118 in in ADP eurjchem-32 110 119     SPACE eurjchem-32 110 120 living live VERB eurjchem-32 110 121     SPACE eurjchem-32 110 122 systems system NOUN eurjchem-32 110 123 . . PUNCT eurjchem-32 110 124     SPACE eurjchem-32 111 1 compounds compounds AUX eurjchem-32 111 2     SPACE eurjchem-32 111 3 containing contain VERB eurjchem-32 111 4     SPACE eurjchem-32 111 5 a a DET eurjchem-32 111 6     SPACE eurjchem-32 111 7 pyrimidine pyrimidine NOUN eurjchem-32 111 8     SPACE eurjchem-32 111 9 ring ring NOUN eurjchem-32 111 10     SPACE eurjchem-32 111 11 has have AUX eurjchem-32 111 12     SPACE eurjchem-32 111 13 been be AUX eurjchem-32 111 14     SPACE eurjchem-32 111 15 reported report VERB eurjchem-32 111 16     SPACE eurjchem-32 111 17 to to PART eurjchem-32 111 18     SPACE eurjchem-32 111 19 exhibit exhibit VERB eurjchem-32 111 20     SPACE eurjchem-32 111 21 antibacterial antibacterial NOUN eurjchem-32 111 22     SPACE eurjchem-32 111 23 and and CCONJ eurjchem-32 111 24     SPACE eurjchem-32 111 25 antifungal antifungal NOUN eurjchem-32 111 26     SPACE eurjchem-32 111 27 as as ADV eurjchem-32 111 28     SPACE eurjchem-32 111 29 well well ADV eurjchem-32 111 30     SPACE eurjchem-32 111 31 as as ADP eurjchem-32 111 32     SPACE eurjchem-32 111 33 anti‐hiv anti‐hiv PROPN eurjchem-32 111 34     SPACE eurjchem-32 111 35 activity activity NOUN eurjchem-32 111 36     SPACE eurjchem-32 112 1 [ [ X eurjchem-32 112 2 21,22 21,22 NOUN eurjchem-32 112 3 ] ] X eurjchem-32 112 4 . . PUNCT eurjchem-32 112 5     SPACE eurjchem-32 112 6 on on ADP eurjchem-32 112 7     SPACE eurjchem-32 112 8 the the DET eurjchem-32 112 9     SPACE eurjchem-32 112 10 other other ADJ eurjchem-32 112 11     SPACE eurjchem-32 112 12 hand hand NOUN eurjchem-32 112 13 , , PUNCT eurjchem-32 112 14     SPACE eurjchem-32 112 15 substitution substitution NOUN eurjchem-32 112 16     SPACE eurjchem-32 112 17 of of ADP eurjchem-32 112 18     SPACE eurjchem-32 112 19 a a DET eurjchem-32 112 20     SPACE eurjchem-32 112 21 pyridine pyridine NOUN eurjchem-32 112 22     SPACE eurjchem-32 112 23 ring ring NOUN eurjchem-32 112 24     SPACE eurjchem-32 112 25 to to PART eurjchem-32 112 26     SPACE eurjchem-32 112 27 benzene benzene NOUN eurjchem-32 112 28     SPACE eurjchem-32 112 29 ring ring NOUN eurjchem-32 112 30     SPACE eurjchem-32 112 31 often often ADV eurjchem-32 112 32     SPACE eurjchem-32 112 33 is be AUX eurjchem-32 112 34     SPACE eurjchem-32 112 35 compatible compatible ADJ eurjchem-32 112 36     SPACE eurjchem-32 112 37 with with ADP eurjchem-32 112 38     SPACE eurjchem-32 112 39 retention retention NOUN eurjchem-32 112 40     SPACE eurjchem-32 112 41 of of ADP eurjchem-32 112 42     SPACE eurjchem-32 112 43 biological biological ADJ eurjchem-32 112 44     SPACE eurjchem-32 112 45 activity activity NOUN eurjchem-32 112 46     SPACE eurjchem-32 112 47 and and CCONJ eurjchem-32 112 48     SPACE eurjchem-32 112 49 occasionally occasionally ADV eurjchem-32 112 50     SPACE eurjchem-32 112 51 the the DET eurjchem-32 112 52     SPACE eurjchem-32 112 53 moiety moiety NOUN eurjchem-32 112 54     SPACE eurjchem-32 112 55 is be AUX eurjchem-32 112 56     SPACE eurjchem-32 112 57 an an DET eurjchem-32 112 58     SPACE eurjchem-32 112 59 essential essential ADJ eurjchem-32 112 60     SPACE eurjchem-32 112 61 part part NOUN eurjchem-32 112 62     SPACE eurjchem-32 112 63 of of ADP eurjchem-32 112 64     SPACE eurjchem-32 112 65 the the DET eurjchem-32 112 66     SPACE eurjchem-32 112 67 pharmacophore pharmacophore NOUN eurjchem-32 112 68 . . PUNCT eurjchem-32 112 69     SPACE eurjchem-32 112 70 such such ADJ eurjchem-32 112 71     SPACE eurjchem-32 112 72 substitution substitution NOUN eurjchem-32 112 73     SPACE eurjchem-32 112 74 of of ADP eurjchem-32 112 75     SPACE eurjchem-32 112 76 = = NOUN eurjchem-32 112 77 n n CCONJ eurjchem-32 112 78     SPACE eurjchem-32 112 79 for for ADP eurjchem-32 112 80     SPACE eurjchem-32 112 81 ch= ch= NOUN eurjchem-32 112 82     SPACE eurjchem-32 112 83 is be AUX eurjchem-32 112 84     SPACE eurjchem-32 112 85 an an DET eurjchem-32 112 86     SPACE eurjchem-32 112 87 example example NOUN eurjchem-32 112 88     SPACE eurjchem-32 112 89 of of ADP eurjchem-32 112 90     SPACE eurjchem-32 112 91 the the DET eurjchem-32 112 92     SPACE eurjchem-32 112 93 common common ADJ eurjchem-32 112 94     SPACE eurjchem-32 112 95 medicinal medicinal ADJ eurjchem-32 112 96     SPACE eurjchem-32 112 97 strategy strategy NOUN eurjchem-32 112 98     SPACE eurjchem-32 112 99 known know VERB eurjchem-32 112 100     SPACE eurjchem-32 112 101 as as ADP eurjchem-32 112 102     SPACE eurjchem-32 112 103 bioisosterism bioisosterism NOUN eurjchem-32 112 104 . . PUNCT eurjchem-32 112 105     SPACE eurjchem-32 112 106 therefore therefore ADV eurjchem-32 112 107 , , PUNCT eurjchem-32 112 108     SPACE eurjchem-32 112 109 5‐amino‐6‐(benzo[d]thiazol‐2‐yl)‐7‐(4‐chlorophen 5‐amino‐6‐(benzo[d]thiazol‐2‐yl)‐7‐(4‐chlorophen NUM eurjchem-32 112 110     SPACE eurjchem-32 112 111 yl)‐2‐thioxo‐2,3‐dihydropyrido[2,3‐d]pyrimidin‐4(1h)‐one yl)‐2‐thioxo‐2,3‐dihydropyrido[2,3‐d]pyrimidin‐4(1h)‐one NOUN eurjchem-32 112 112     SPACE eurjchem-32 112 113 8 8 NUM eurjchem-32 112 114     SPACE eurjchem-32 112 115 was be AUX eurjchem-32 112 116     SPACE eurjchem-32 112 117 synthesized synthesize VERB eurjchem-32 112 118     SPACE eurjchem-32 112 119 by by ADP eurjchem-32 112 120     SPACE eurjchem-32 112 121 refluxing refluxing NOUN eurjchem-32 112 122     SPACE eurjchem-32 112 123 equimolar equimolar NOUN eurjchem-32 112 124     SPACE eurjchem-32 112 125 amounts amount NOUN eurjchem-32 112 126     SPACE eurjchem-32 112 127 of of ADP eurjchem-32 112 128     SPACE eurjchem-32 112 129 compound compound NOUN eurjchem-32 112 130     SPACE eurjchem-32 112 131 4 4 NUM eurjchem-32 112 132 , , PUNCT eurjchem-32 112 133     SPACE eurjchem-32 112 134 6‐aminothiouracil 6‐aminothiouracil NUM eurjchem-32 112 135     SPACE eurjchem-32 112 136 7 7 NUM eurjchem-32 112 137     SPACE eurjchem-32 112 138 and and CCONJ eurjchem-32 112 139     SPACE eurjchem-32 112 140 p‐chlorobenzaldehyde p‐chlorobenzaldehyde NOUN eurjchem-32 112 141     SPACE eurjchem-32 112 142 in in ADP eurjchem-32 112 143     SPACE eurjchem-32 112 144 ethanol ethanol NOUN eurjchem-32 112 145     SPACE eurjchem-32 112 146 in in ADP eurjchem-32 112 147     SPACE eurjchem-32 112 148 presence presence NOUN eurjchem-32 112 149     SPACE eurjchem-32 112 150 of of ADP eurjchem-32 112 151     SPACE eurjchem-32 112 152 a a DET eurjchem-32 112 153     SPACE eurjchem-32 112 154 catalytic catalytic ADJ eurjchem-32 112 155     SPACE eurjchem-32 112 156 amount amount NOUN eurjchem-32 112 157     SPACE eurjchem-32 112 158 of of ADP eurjchem-32 112 159     SPACE eurjchem-32 112 160 piperidine piperidine NOUN eurjchem-32 112 161 . . PUNCT eurjchem-32 112 162     SPACE eurjchem-32 113 1 the the DET eurjchem-32 113 2     SPACE eurjchem-32 113 3 reaction reaction NOUN eurjchem-32 113 4     SPACE eurjchem-32 113 5 proceeded proceed VERB eurjchem-32 113 6     SPACE eurjchem-32 113 7 according accord VERB eurjchem-32 113 8     SPACE eurjchem-32 113 9 to to PART eurjchem-32 113 10     SPACE eurjchem-32 113 11 scheme scheme VERB eurjchem-32 113 12     SPACE eurjchem-32 113 13 4 4 NUM eurjchem-32 113 14 . . PUNCT eurjchem-32 113 15     SPACE eurjchem-32 113 16 the the DET eurjchem-32 113 17     SPACE eurjchem-32 113 18 formation formation NOUN eurjchem-32 113 19     SPACE eurjchem-32 113 20 of of ADP eurjchem-32 113 21     SPACE eurjchem-32 113 22 8 8 NUM eurjchem-32 113 23     SPACE eurjchem-32 113 24 can can AUX eurjchem-32 113 25     SPACE eurjchem-32 113 26 be be AUX eurjchem-32 113 27     SPACE eurjchem-32 113 28 attributed attribute VERB eurjchem-32 113 29     SPACE eurjchem-32 113 30 to to ADP eurjchem-32 113 31     SPACE eurjchem-32 113 32 the the DET eurjchem-32 113 33     SPACE eurjchem-32 113 34 first first ADJ eurjchem-32 113 35     SPACE eurjchem-32 113 36 formation formation NOUN eurjchem-32 113 37     SPACE eurjchem-32 113 38 of of ADP eurjchem-32 113 39     SPACE eurjchem-32 113 40 compound compound NOUN eurjchem-32 113 41     SPACE eurjchem-32 113 42 5 5 NUM eurjchem-32 113 43     SPACE eurjchem-32 113 44 as as ADP eurjchem-32 113 45     SPACE eurjchem-32 113 46 intermediate intermediate ADJ eurjchem-32 113 47     SPACE eurjchem-32 113 48 which which PRON eurjchem-32 113 49     SPACE eurjchem-32 113 50 undergo undergo VERB eurjchem-32 113 51     SPACE eurjchem-32 113 52 michael michael PROPN eurjchem-32 113 53     SPACE eurjchem-32 113 54 reaction reaction NOUN eurjchem-32 113 55     SPACE eurjchem-32 113 56 with with ADP eurjchem-32 113 57     SPACE eurjchem-32 113 58 6‐aminothiouracil 6‐aminothiouracil NUM eurjchem-32 113 59     SPACE eurjchem-32 113 60 7 7 NUM eurjchem-32 113 61     SPACE eurjchem-32 113 62 to to PART eurjchem-32 113 63     SPACE eurjchem-32 113 64 yield yield VERB eurjchem-32 113 65     SPACE eurjchem-32 113 66 the the DET eurjchem-32 113 67     SPACE eurjchem-32 113 68 nonionisable nonionisable ADJ eurjchem-32 113 69     SPACE eurjchem-32 113 70 intermediate intermediate ADJ eurjchem-32 113 71     SPACE eurjchem-32 113 72 a a PRON eurjchem-32 113 73     SPACE eurjchem-32 113 74 which which PRON eurjchem-32 113 75     SPACE eurjchem-32 113 76 undergo undergo VERB eurjchem-32 113 77     SPACE eurjchem-32 113 78 intra‐molecular intra‐molecular ADJ eurjchem-32 113 79     SPACE eurjchem-32 113 80 nucleophilic nucleophilic ADJ eurjchem-32 113 81     SPACE eurjchem-32 113 82 addition addition NOUN eurjchem-32 113 83     SPACE eurjchem-32 113 84 to to ADP eurjchem-32 113 85     SPACE eurjchem-32 113 86 the the DET eurjchem-32 113 87     SPACE eurjchem-32 113 88 cn cn PROPN eurjchem-32 113 89     SPACE eurjchem-32 113 90 group group NOUN eurjchem-32 113 91     SPACE eurjchem-32 113 92 to to PART eurjchem-32 113 93     SPACE eurjchem-32 113 94 give give VERB eurjchem-32 113 95     SPACE eurjchem-32 113 96 the the DET eurjchem-32 113 97     SPACE eurjchem-32 113 98 intermediate intermediate ADJ eurjchem-32 113 99     SPACE eurjchem-32 113 100 b b NOUN eurjchem-32 113 101     SPACE eurjchem-32 113 102 which which PRON eurjchem-32 113 103     SPACE eurjchem-32 113 104 is be AUX eurjchem-32 113 105     SPACE eurjchem-32 113 106 aromatized aromatize VERB eurjchem-32 113 107     SPACE eurjchem-32 113 108 under under ADP eurjchem-32 113 109     SPACE eurjchem-32 113 110 the the DET eurjchem-32 113 111     SPACE eurjchem-32 113 112 reaction reaction NOUN eurjchem-32 113 113     SPACE eurjchem-32 113 114 condition condition NOUN eurjchem-32 113 115     SPACE eurjchem-32 113 116 to to PART eurjchem-32 113 117     SPACE eurjchem-32 113 118 afford afford VERB eurjchem-32 113 119     SPACE eurjchem-32 113 120 the the DET eurjchem-32 113 121     SPACE eurjchem-32 113 122 final final ADJ eurjchem-32 113 123     SPACE eurjchem-32 113 124 isolable isolable ADJ eurjchem-32 113 125     SPACE eurjchem-32 113 126 product product NOUN eurjchem-32 113 127     SPACE eurjchem-32 113 128 8 8 NUM eurjchem-32 113 129     SPACE eurjchem-32 113 130 ( ( PUNCT eurjchem-32 113 131 scheme scheme NOUN eurjchem-32 113 132     SPACE eurjchem-32 113 133 4 4 NUM eurjchem-32 113 134 ) ) PUNCT eurjchem-32 113 135 . . PUNCT eurjchem-32 113 136     SPACE eurjchem-32 114 1 the the DET eurjchem-32 114 2     SPACE eurjchem-32 114 3 structure structure NOUN eurjchem-32 114 4     SPACE eurjchem-32 114 5 of of ADP eurjchem-32 114 6     SPACE eurjchem-32 114 7 compound compound NOUN eurjchem-32 114 8     SPACE eurjchem-32 114 9 8 8 NUM eurjchem-32 114 10     SPACE eurjchem-32 114 11 was be AUX eurjchem-32 114 12     SPACE eurjchem-32 114 13 proved prove VERB eurjchem-32 114 14     SPACE eurjchem-32 114 15 by by ADP eurjchem-32 114 16     SPACE eurjchem-32 114 17 its its PRON eurjchem-32 114 18     SPACE eurjchem-32 114 19 analytical analytical NOUN eurjchem-32 114 20     SPACE eurjchem-32 114 21 and and CCONJ eurjchem-32 114 22     SPACE eurjchem-32 114 23 spectral spectral ADJ eurjchem-32 114 24     SPACE eurjchem-32 114 25 analyses analysis NOUN eurjchem-32 114 26 . . PUNCT eurjchem-32 114 27     SPACE eurjchem-32 115 1 the the DET eurjchem-32 115 2     SPACE eurjchem-32 115 3 mass mass PROPN eurjchem-32 115 4     SPACE eurjchem-32 115 5 spectrum spectrum NOUN eurjchem-32 115 6     SPACE eurjchem-32 115 7 showed show VERB eurjchem-32 115 8     SPACE eurjchem-32 115 9 a a DET eurjchem-32 115 10     SPACE eurjchem-32 115 11 molecular molecular ADJ eurjchem-32 115 12     SPACE eurjchem-32 115 13 ion ion NOUN eurjchem-32 115 14     SPACE eurjchem-32 115 15 peak peak NOUN eurjchem-32 115 16     SPACE eurjchem-32 115 17 at at ADP eurjchem-32 115 18     SPACE eurjchem-32 115 19 m m PROPN eurjchem-32 115 20 / / PROPN eurjchem-32 115 21 z z NOUN eurjchem-32 115 22     SPACE eurjchem-32 115 23 438 438 NUM eurjchem-32 115 24     SPACE eurjchem-32 115 25 ( ( PUNCT eurjchem-32 115 26 m+ m+ NUM eurjchem-32 115 27 ) ) PUNCT eurjchem-32 115 28 . . PUNCT eurjchem-32 115 29     SPACE eurjchem-32 116 1 the the DET eurjchem-32 116 2     SPACE eurjchem-32 116 3 ir ir PROPN eurjchem-32 116 4     SPACE eurjchem-32 116 5 spectrum spectrum NOUN eurjchem-32 116 6     SPACE eurjchem-32 116 7 showed show VERB eurjchem-32 116 8     SPACE eurjchem-32 116 9 absorption absorption NOUN eurjchem-32 116 10     SPACE eurjchem-32 116 11 bands band NOUN eurjchem-32 116 12     SPACE eurjchem-32 116 13 at at ADP eurjchem-32 116 14     SPACE eurjchem-32 116 15 3402 3402 NUM eurjchem-32 116 16 , , PUNCT eurjchem-32 116 17     SPACE eurjchem-32 116 18 3389 3389 NUM eurjchem-32 116 19     SPACE eurjchem-32 116 20 cm‐1 cm‐1 NOUN eurjchem-32 116 21     SPACE eurjchem-32 116 22 ( ( PUNCT eurjchem-32 116 23 nh2 nh2 PROPN eurjchem-32 116 24 ) ) PUNCT eurjchem-32 116 25 , , PUNCT eurjchem-32 116 26     SPACE eurjchem-32 116 27 3141 3141 NUM eurjchem-32 116 28     SPACE eurjchem-32 116 29 cm‐1 cm‐1 NOUN eurjchem-32 116 30     SPACE eurjchem-32 116 31 ( ( PUNCT eurjchem-32 116 32 nh nh NOUN eurjchem-32 116 33 ) ) PUNCT eurjchem-32 116 34 , , PUNCT eurjchem-32 116 35     SPACE eurjchem-32 116 36 1698 1698 NUM eurjchem-32 116 37     SPACE eurjchem-32 116 38 cm‐1 cm‐1 NOUN eurjchem-32 116 39     SPACE eurjchem-32 116 40 ( ( PUNCT eurjchem-32 116 41 c c NOUN eurjchem-32 116 42 = = NOUN eurjchem-32 116 43 o o NOUN eurjchem-32 116 44 ) ) PUNCT eurjchem-32 116 45     SPACE eurjchem-32 116 46 and and CCONJ eurjchem-32 116 47     SPACE eurjchem-32 116 48 1221 1221 NUM eurjchem-32 116 49     SPACE eurjchem-32 116 50 cm‐1 cm‐1 NOUN eurjchem-32 116 51       SPACE eurjchem-32 116 52 ( ( PUNCT eurjchem-32 116 53 c c PROPN eurjchem-32 116 54 = = SYM eurjchem-32 116 55 s s NOUN eurjchem-32 116 56 ) ) PUNCT eurjchem-32 116 57 ; ; PUNCT eurjchem-32 116 58     SPACE eurjchem-32 116 59 1h 1h NUM eurjchem-32 116 60     SPACE eurjchem-32 116 61 nmr nmr NOUN eurjchem-32 116 62     SPACE eurjchem-32 116 63 ( ( PUNCT eurjchem-32 116 64 dmso‐d6 dmso‐d6 NOUN eurjchem-32 116 65 ) ) PUNCT eurjchem-32 116 66     SPACE eurjchem-32 116 67 showed show VERB eurjchem-32 116 68     SPACE eurjchem-32 116 69 three three NUM eurjchem-32 116 70     SPACE eurjchem-32 116 71 d2o d2o NOUN eurjchem-32 116 72     SPACE eurjchem-32 116 73 exchangeable exchangeable ADJ eurjchem-32 116 74     SPACE eurjchem-32 116 75 protons proton NOUN eurjchem-32 116 76     SPACE eurjchem-32 116 77 at at ADP eurjchem-32 116 78     SPACE eurjchem-32 116 79 δ δ PROPN eurjchem-32 116 80     SPACE eurjchem-32 116 81 13.51 13.51 NUM eurjchem-32 116 82 , , PUNCT eurjchem-32 116 83     SPACE eurjchem-32 116 84 13 13 NUM eurjchem-32 116 85 . . PUNCT eurjchem-32 116 86     SPACE eurjchem-32 116 87 59 59 NUM eurjchem-32 116 88     SPACE eurjchem-32 116 89 ppm ppm NOUN eurjchem-32 116 90     SPACE eurjchem-32 116 91 due due ADJ eurjchem-32 116 92     SPACE eurjchem-32 116 93 to to ADP eurjchem-32 116 94     SPACE eurjchem-32 116 95 nh nh NOUN eurjchem-32 116 96     SPACE eurjchem-32 116 97 protons proton NOUN eurjchem-32 116 98     SPACE eurjchem-32 116 99 and and CCONJ eurjchem-32 116 100     SPACE eurjchem-32 116 101 at at ADP eurjchem-32 116 102     SPACE eurjchem-32 116 103 δ δ PROPN eurjchem-32 116 104     SPACE eurjchem-32 116 105 6.22 6.22 NUM eurjchem-32 116 106     SPACE eurjchem-32 116 107 ppm ppm NOUN eurjchem-32 116 108     SPACE eurjchem-32 116 109 due due ADJ eurjchem-32 116 110     SPACE eurjchem-32 116 111 to to PART eurjchem-32 116 112     SPACE eurjchem-32 116 113 nh2 nh2 PROPN eurjchem-32 116 114     SPACE eurjchem-32 116 115 beside beside ADP eurjchem-32 116 116     SPACE eurjchem-32 116 117 the the DET eurjchem-32 116 118     SPACE eurjchem-32 116 119 aromatic aromatic ADJ eurjchem-32 116 120     SPACE eurjchem-32 116 121 protons proton NOUN eurjchem-32 116 122 . . PUNCT eurjchem-32 116 123     SPACE eurjchem-32 117 1 an an DET eurjchem-32 117 2     SPACE eurjchem-32 117 3 alternative alternative ADJ eurjchem-32 117 4     SPACE eurjchem-32 117 5 method method NOUN eurjchem-32 117 6     SPACE eurjchem-32 117 7 for for ADP eurjchem-32 117 8     SPACE eurjchem-32 117 9 the the DET eurjchem-32 117 10     SPACE eurjchem-32 117 11 synthesis synthesis NOUN eurjchem-32 117 12     SPACE eurjchem-32 117 13 of of ADP eurjchem-32 117 14     SPACE eurjchem-32 117 15 compound compound NOUN eurjchem-32 117 16     SPACE eurjchem-32 117 17 8 8 NUM eurjchem-32 117 18     SPACE eurjchem-32 117 19 was be AUX eurjchem-32 117 20     SPACE eurjchem-32 117 21 achieved achieve VERB eurjchem-32 117 22     SPACE eurjchem-32 117 23 by by ADP eurjchem-32 117 24     SPACE eurjchem-32 117 25 heating heating NOUN eurjchem-32 117 26     SPACE eurjchem-32 117 27 benzothiazole benzothiazole NOUN eurjchem-32 117 28     SPACE eurjchem-32 117 29 derivative derivative NOUN eurjchem-32 117 30     SPACE eurjchem-32 117 31 5 5 NUM eurjchem-32 117 32     SPACE eurjchem-32 117 33 with with ADP eurjchem-32 117 34     SPACE eurjchem-32 117 35 6‐aminouracil 6‐aminouracil NOUN eurjchem-32 117 36     SPACE eurjchem-32 117 37 ( ( PUNCT eurjchem-32 117 38 7 7 NUM eurjchem-32 117 39 ) ) PUNCT eurjchem-32 117 40     SPACE eurjchem-32 117 41 in in ADP eurjchem-32 117 42     SPACE eurjchem-32 117 43 dmf dmf NOUN eurjchem-32 117 44     SPACE eurjchem-32 117 45 and and CCONJ eurjchem-32 117 46     SPACE eurjchem-32 117 47 in in ADP eurjchem-32 117 48     SPACE eurjchem-32 117 49 the the DET eurjchem-32 117 50     SPACE eurjchem-32 117 51 presence presence NOUN eurjchem-32 117 52     SPACE eurjchem-32 117 53 of of ADP eurjchem-32 117 54     SPACE eurjchem-32 117 55 piperidine piperidine NOUN eurjchem-32 117 56     SPACE eurjchem-32 117 57 ( ( PUNCT eurjchem-32 117 58 catalytic catalytic ADJ eurjchem-32 117 59     SPACE eurjchem-32 117 60 amount amount NOUN eurjchem-32 117 61 ) ) PUNCT eurjchem-32 117 62     SPACE eurjchem-32 117 63 to to PART eurjchem-32 117 64     SPACE eurjchem-32 117 65 give give VERB eurjchem-32 117 66     SPACE eurjchem-32 117 67 a a DET eurjchem-32 117 68     SPACE eurjchem-32 117 69 product product NOUN eurjchem-32 117 70     SPACE eurjchem-32 117 71 identical identical ADJ eurjchem-32 117 72     SPACE eurjchem-32 117 73 in in ADP eurjchem-32 117 74     SPACE eurjchem-32 117 75 all all DET eurjchem-32 117 76     SPACE eurjchem-32 117 77 respects respect NOUN eurjchem-32 117 78     SPACE eurjchem-32 117 79 ( ( PUNCT eurjchem-32 117 80 m.p m.p PROPN eurjchem-32 117 81 . . PROPN eurjchem-32 117 82 , , PUNCT eurjchem-32 117 83     SPACE eurjchem-32 117 84 mixed mix VERB eurjchem-32 117 85     SPACE eurjchem-32 117 86 m.p m.p PROPN eurjchem-32 117 87 . . PROPN eurjchem-32 117 88 , , PUNCT eurjchem-32 117 89     SPACE eurjchem-32 117 90 ir ir PROPN eurjchem-32 117 91 , , PUNCT eurjchem-32 117 92     SPACE eurjchem-32 117 93 and and CCONJ eurjchem-32 117 94     SPACE eurjchem-32 117 95 1h 1h NUM eurjchem-32 117 96     SPACE eurjchem-32 117 97 nmr nmr NOUN eurjchem-32 117 98 ) ) PUNCT eurjchem-32 117 99     SPACE eurjchem-32 117 100 with with ADP eurjchem-32 117 101     SPACE eurjchem-32 117 102 8 8 NUM eurjchem-32 117 103 . . PUNCT eurjchem-32 117 104     SPACE eurjchem-32 117 105 similarly similarly ADV eurjchem-32 117 106 , , PUNCT eurjchem-32 117 107     SPACE eurjchem-32 117 108 it it PRON eurjchem-32 117 109     SPACE eurjchem-32 117 110 was be AUX eurjchem-32 117 111     SPACE eurjchem-32 117 112 found find VERB eurjchem-32 117 113     SPACE eurjchem-32 117 114 that that SCONJ eurjchem-32 117 115     SPACE eurjchem-32 117 116 refluxing refluxing NOUN eurjchem-32 117 117     SPACE eurjchem-32 117 118 a a DET eurjchem-32 117 119     SPACE eurjchem-32 117 120 mixture mixture NOUN eurjchem-32 117 121     SPACE eurjchem-32 117 122 of of ADP eurjchem-32 117 123     SPACE eurjchem-32 117 124 compound compound NOUN eurjchem-32 117 125     SPACE eurjchem-32 117 126 4 4 NUM eurjchem-32 117 127 , , PUNCT eurjchem-32 117 128     SPACE eurjchem-32 117 129 1‐methyl‐6‐aminouracil 1‐methyl‐6‐aminouracil NUM eurjchem-32 117 130     SPACE eurjchem-32 117 131 9 9 NUM eurjchem-32 117 132     SPACE eurjchem-32 117 133 and and CCONJ eurjchem-32 117 134     SPACE eurjchem-32 117 135 3‐formylpyrazole 3‐formylpyrazole NUM eurjchem-32 117 136     SPACE eurjchem-32 117 137 10 10 NUM eurjchem-32 117 138     SPACE eurjchem-32 117 139 in in ADP eurjchem-32 117 140     SPACE eurjchem-32 117 141 dmf dmf PROPN eurjchem-32 117 142     SPACE eurjchem-32 117 143 in in ADP eurjchem-32 117 144     SPACE eurjchem-32 117 145 the the DET eurjchem-32 117 146     SPACE eurjchem-32 117 147 presence presence NOUN eurjchem-32 117 148     SPACE eurjchem-32 117 149 of of ADP eurjchem-32 117 150     SPACE eurjchem-32 117 151 tea tea NOUN eurjchem-32 117 152     SPACE eurjchem-32 117 153 afforded afford VERB eurjchem-32 117 154     SPACE eurjchem-32 117 155 the the DET eurjchem-32 117 156     SPACE eurjchem-32 117 157 corresponding corresponding ADJ eurjchem-32 117 158     SPACE eurjchem-32 117 159 pyridopyrimidine pyridopyrimidine NOUN eurjchem-32 117 160     SPACE eurjchem-32 117 161 derivative derivative NOUN eurjchem-32 117 162     SPACE eurjchem-32 117 163 11 11 NUM eurjchem-32 117 164     SPACE eurjchem-32 117 165 ( ( PUNCT eurjchem-32 117 166 scheme scheme NOUN eurjchem-32 117 167     SPACE eurjchem-32 117 168 5 5 NUM eurjchem-32 117 169 ) ) PUNCT eurjchem-32 117 170 . . PUNCT eurjchem-32 117 171     SPACE eurjchem-32 118 1 the the DET eurjchem-32 118 2     SPACE eurjchem-32 118 3 formation formation NOUN eurjchem-32 118 4     SPACE eurjchem-32 118 5 of of ADP eurjchem-32 118 6     SPACE eurjchem-32 118 7 11 11 NUM eurjchem-32 118 8     SPACE eurjchem-32 118 9 apparently apparently ADV eurjchem-32 118 10     SPACE eurjchem-32 118 11 proceeded proceeded AUX eurjchem-32 118 12     SPACE eurjchem-32 118 13 according accord VERB eurjchem-32 118 14     SPACE eurjchem-32 118 15 to to ADP eurjchem-32 118 16     SPACE eurjchem-32 118 17 the the DET eurjchem-32 118 18     SPACE eurjchem-32 118 19 previously previously ADV eurjchem-32 118 20     SPACE eurjchem-32 118 21 proposed propose VERB eurjchem-32 118 22     SPACE eurjchem-32 118 23 mechanism mechanism NOUN eurjchem-32 118 24     SPACE eurjchem-32 118 25 and and CCONJ eurjchem-32 118 26     SPACE eurjchem-32 118 27 its its PRON eurjchem-32 118 28     SPACE eurjchem-32 118 29 structure structure NOUN eurjchem-32 118 30     SPACE eurjchem-32 118 31 was be AUX eurjchem-32 118 32     SPACE eurjchem-32 118 33 proved prove VERB eurjchem-32 118 34     SPACE eurjchem-32 118 35 by by ADP eurjchem-32 118 36     SPACE eurjchem-32 118 37 analytical analytical ADJ eurjchem-32 118 38     SPACE eurjchem-32 118 39 and and CCONJ eurjchem-32 118 40     SPACE eurjchem-32 118 41 spectral spectral ADJ eurjchem-32 118 42     SPACE eurjchem-32 118 43 analyses analysis NOUN eurjchem-32 118 44 . . PUNCT eurjchem-32 118 45     SPACE eurjchem-32 119 1 the the DET eurjchem-32 119 2     SPACE eurjchem-32 119 3 ir ir NOUN eurjchem-32 119 4     SPACE eurjchem-32 119 5 spectrum spectrum NOUN eurjchem-32 119 6     SPACE eurjchem-32 119 7 of of ADP eurjchem-32 119 8     SPACE eurjchem-32 119 9 11 11 NUM eurjchem-32 119 10     SPACE eurjchem-32 119 11 revealed reveal VERB eurjchem-32 119 12     SPACE eurjchem-32 119 13 absorption absorption NOUN eurjchem-32 119 14     SPACE eurjchem-32 119 15 bands band NOUN eurjchem-32 119 16     SPACE eurjchem-32 119 17 at at ADP eurjchem-32 119 18     SPACE eurjchem-32 119 19 3400 3400 NUM eurjchem-32 119 20 , , PUNCT eurjchem-32 119 21     SPACE eurjchem-32 119 22 3365 3365 NUM eurjchem-32 119 23     SPACE eurjchem-32 119 24 cm‐1 cm‐1 NOUN eurjchem-32 119 25     SPACE eurjchem-32 119 26 ( ( PUNCT eurjchem-32 119 27 nh2 nh2 PROPN eurjchem-32 119 28 ) ) PUNCT eurjchem-32 119 29 , , PUNCT eurjchem-32 119 30     SPACE eurjchem-32 119 31 3220 3220 NUM eurjchem-32 119 32     SPACE eurjchem-32 119 33 and and CCONJ eurjchem-32 119 34     SPACE eurjchem-32 119 35 1695 1695 NUM eurjchem-32 119 36     SPACE eurjchem-32 119 37 cm‐1 cm‐1 NOUN eurjchem-32 119 38     SPACE eurjchem-32 119 39 ( ( PUNCT eurjchem-32 119 40 nh nh NOUN eurjchem-32 119 41     SPACE eurjchem-32 119 42 and and CCONJ eurjchem-32 119 43     SPACE eurjchem-32 119 44 amidic amidic NOUN eurjchem-32 119 45     SPACE eurjchem-32 119 46 co co NOUN eurjchem-32 119 47     SPACE eurjchem-32 119 48 group group NOUN eurjchem-32 119 49 , , PUNCT eurjchem-32 119 50     SPACE eurjchem-32 119 51 respectively respectively ADV eurjchem-32 119 52 ) ) PUNCT eurjchem-32 119 53 . . PUNCT eurjchem-32 119 54     SPACE eurjchem-32 120 1 the the DET eurjchem-32 120 2     SPACE eurjchem-32 120 3 mass mass PROPN eurjchem-32 120 4     SPACE eurjchem-32 120 5 spectrum spectrum NOUN eurjchem-32 120 6     SPACE eurjchem-32 120 7 showed show VERB eurjchem-32 120 8     SPACE eurjchem-32 120 9 the the DET eurjchem-32 120 10     SPACE eurjchem-32 120 11 molecular molecular ADJ eurjchem-32 120 12     SPACE eurjchem-32 120 13 ion ion NOUN eurjchem-32 120 14     SPACE eurjchem-32 120 15 peak peak NOUN eurjchem-32 120 16     SPACE eurjchem-32 120 17 at at ADP eurjchem-32 120 18     SPACE eurjchem-32 120 19 m m PROPN eurjchem-32 120 20 / / PROPN eurjchem-32 120 21 z z NOUN eurjchem-32 120 22     SPACE eurjchem-32 120 23 543 543 NUM eurjchem-32 120 24     SPACE eurjchem-32 120 25 ( ( PUNCT eurjchem-32 120 26 m+ m+ NUM eurjchem-32 120 27 , , PUNCT eurjchem-32 120 28     SPACE eurjchem-32 120 29 10 10 NUM eurjchem-32 120 30 % % NOUN eurjchem-32 120 31 ) ) PUNCT eurjchem-32 120 32 . . PUNCT eurjchem-32 120 33     SPACE eurjchem-32 121 1 in in ADP eurjchem-32 121 2     SPACE eurjchem-32 121 3 a a DET eurjchem-32 121 4     SPACE eurjchem-32 121 5 similar similar ADJ eurjchem-32 121 6     SPACE eurjchem-32 121 7 way way NOUN eurjchem-32 121 8 , , PUNCT eurjchem-32 121 9     SPACE eurjchem-32 121 10 heating heat VERB eurjchem-32 121 11     SPACE eurjchem-32 121 12 4 4 NUM eurjchem-32 121 13     SPACE eurjchem-32 121 14 with with ADP eurjchem-32 121 15     SPACE eurjchem-32 121 16 an an DET eurjchem-32 121 17     SPACE eurjchem-32 121 18 equimolar equimolar NOUN eurjchem-32 121 19     SPACE eurjchem-32 121 20 amounts amount NOUN eurjchem-32 121 21     SPACE eurjchem-32 121 22 of of ADP eurjchem-32 121 23     SPACE eurjchem-32 121 24 pipronal pipronal ADJ eurjchem-32 121 25     SPACE eurjchem-32 121 26 12 12 NUM eurjchem-32 121 27     SPACE eurjchem-32 121 28 and and CCONJ eurjchem-32 121 29     SPACE eurjchem-32 121 30 1,3‐dimethyl‐6‐aminouracil 1,3‐dimethyl‐6‐aminouracil NUM eurjchem-32 121 31     SPACE eurjchem-32 121 32 13 13 NUM eurjchem-32 121 33     SPACE eurjchem-32 121 34 in in ADP eurjchem-32 121 35     SPACE eurjchem-32 121 36 dmf dmf PROPN eurjchem-32 121 37     SPACE eurjchem-32 121 38 in in ADP eurjchem-32 121 39     SPACE eurjchem-32 121 40 the the DET eurjchem-32 121 41     SPACE eurjchem-32 121 42 presence presence NOUN eurjchem-32 121 43     SPACE eurjchem-32 121 44 of of ADP eurjchem-32 121 45     SPACE eurjchem-32 121 46 a a DET eurjchem-32 121 47     SPACE eurjchem-32 121 48 catalytic catalytic ADJ eurjchem-32 121 49     SPACE eurjchem-32 121 50 amount amount NOUN eurjchem-32 121 51     SPACE eurjchem-32 121 52 of of ADP eurjchem-32 121 53     SPACE eurjchem-32 121 54 tea tea NOUN eurjchem-32 121 55     SPACE eurjchem-32 121 56 gave give VERB eurjchem-32 121 57     SPACE eurjchem-32 121 58 the the DET eurjchem-32 121 59     SPACE eurjchem-32 121 60 corresponding corresponding ADJ eurjchem-32 121 61     SPACE eurjchem-32 121 62 pyridopyrimidine pyridopyrimidine NOUN eurjchem-32 121 63     SPACE eurjchem-32 121 64 derivative derivative NOUN eurjchem-32 121 65     SPACE eurjchem-32 121 66 14 14 NUM eurjchem-32 121 67     SPACE eurjchem-32 121 68 ( ( PUNCT eurjchem-32 121 69 scheme scheme NOUN eurjchem-32 121 70     SPACE eurjchem-32 121 71 6 6 NUM eurjchem-32 121 72 ) ) PUNCT eurjchem-32 121 73 . . PUNCT eurjchem-32 121 74     SPACE eurjchem-32 122 1 on on ADP eurjchem-32 122 2     SPACE eurjchem-32 122 3 the the DET eurjchem-32 122 4     SPACE eurjchem-32 122 5 other other ADJ eurjchem-32 122 6     SPACE eurjchem-32 122 7 hand hand NOUN eurjchem-32 122 8 , , PUNCT eurjchem-32 122 9     SPACE eurjchem-32 122 10 it it PRON eurjchem-32 122 11     SPACE eurjchem-32 122 12 was be AUX eurjchem-32 122 13     SPACE eurjchem-32 122 14 found find VERB eurjchem-32 122 15     SPACE eurjchem-32 122 16 that that SCONJ eurjchem-32 122 17     SPACE eurjchem-32 122 18 refluxing refluxing NOUN eurjchem-32 122 19     SPACE eurjchem-32 122 20 2‐ 2‐ NUM eurjchem-32 122 21 ( ( PUNCT eurjchem-32 122 22 benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile benzo[d]thiazol‐2‐yl)‐3‐oxopentanedinitrile NOUN eurjchem-32 122 23     SPACE eurjchem-32 122 24 with with ADP eurjchem-32 122 25     SPACE eurjchem-32 122 26 p‐tolualde p‐tolualde PUNCT eurjchem-32 122 27     SPACE eurjchem-32 122 28 hyde hyde NOUN eurjchem-32 122 29     SPACE eurjchem-32 122 30 in in ADP eurjchem-32 122 31     SPACE eurjchem-32 122 32 glacial glacial ADJ eurjchem-32 122 33     SPACE eurjchem-32 122 34 acetic acetic ADJ eurjchem-32 122 35     SPACE eurjchem-32 122 36 acid acid NOUN eurjchem-32 122 37     SPACE eurjchem-32 122 38 in in ADP eurjchem-32 122 39     SPACE eurjchem-32 122 40 the the DET eurjchem-32 122 41     SPACE eurjchem-32 122 42 presence presence NOUN eurjchem-32 122 43     SPACE eurjchem-32 122 44 of of ADP eurjchem-32 122 45     SPACE eurjchem-32 122 46 freshly freshly ADV eurjchem-32 122 47     SPACE eurjchem-32 122 48 fused fuse VERB eurjchem-32 122 49     SPACE eurjchem-32 122 50 sodium sodium NOUN eurjchem-32 122 51     SPACE eurjchem-32 122 52 acetate acetate NOUN eurjchem-32 122 53     SPACE eurjchem-32 122 54 afforded afford VERB eurjchem-32 122 55     SPACE eurjchem-32 122 56 2‐(benzo[d]thiazol‐2‐yl)‐4‐(4‐ 2‐(benzo[d]thiazol‐2‐yl)‐4‐(4‐ PROPN eurjchem-32 122 57 methylbenzylidene)‐3‐oxopentanedinitrile methylbenzylidene)‐3‐oxopentanedinitrile NOUN eurjchem-32 122 58     SPACE eurjchem-32 122 59 15 15 NUM eurjchem-32 122 60     SPACE eurjchem-32 122 61 ( ( PUNCT eurjchem-32 122 62 scheme scheme NOUN eurjchem-32 122 63     SPACE eurjchem-32 122 64 7 7 NUM eurjchem-32 122 65 ) ) PUNCT eurjchem-32 122 66 . . PUNCT eurjchem-32 122 67     SPACE eurjchem-32 123 1 the the DET eurjchem-32 123 2     SPACE eurjchem-32 123 3 1h 1h NUM eurjchem-32 123 4     SPACE eurjchem-32 123 5 nmr nmr NOUN eurjchem-32 123 6     SPACE eurjchem-32 123 7 spectrum spectrum NOUN eurjchem-32 123 8     SPACE eurjchem-32 123 9 of of ADP eurjchem-32 123 10     SPACE eurjchem-32 123 11 15 15 NUM eurjchem-32 123 12     SPACE eurjchem-32 123 13 showed show VERB eurjchem-32 123 14     SPACE eurjchem-32 123 15 singlet singlet NOUN eurjchem-32 123 16     SPACE eurjchem-32 123 17 signals signal NOUN eurjchem-32 123 18     SPACE eurjchem-32 123 19 at at ADP eurjchem-32 123 20     SPACE eurjchem-32 123 21 δ δ PROPN eurjchem-32 123 22     SPACE eurjchem-32 123 23 2.49 2.49 NUM eurjchem-32 123 24 , , PUNCT eurjchem-32 123 25     SPACE eurjchem-32 123 26 δ δ PROPN eurjchem-32 123 27     SPACE eurjchem-32 123 28 5.70 5.70 NUM eurjchem-32 123 29 , , PUNCT eurjchem-32 123 30     SPACE eurjchem-32 123 31 δ δ PROPN eurjchem-32 123 32     SPACE eurjchem-32 123 33 6.30 6.30 NUM eurjchem-32 123 34     SPACE eurjchem-32 123 35 ppm ppm NOUN eurjchem-32 123 36     SPACE eurjchem-32 123 37 and and CCONJ eurjchem-32 123 38     SPACE eurjchem-32 123 39 multiplet multiplet NOUN eurjchem-32 123 40     SPACE eurjchem-32 123 41 signal signal NOUN eurjchem-32 123 42     SPACE eurjchem-32 123 43 at at ADP eurjchem-32 123 44     SPACE eurjchem-32 123 45 δ δ PROPN eurjchem-32 123 46     SPACE eurjchem-32 123 47 7.19‐8.10 7.19‐8.10 NOUN eurjchem-32 123 48     SPACE eurjchem-32 123 49 ppm ppm ADJ eurjchem-32 123 50     SPACE eurjchem-32 123 51 due due ADJ eurjchem-32 123 52     SPACE eurjchem-32 123 53 to to ADP eurjchem-32 123 54     SPACE eurjchem-32 123 55 ch3 ch3 PROPN eurjchem-32 123 56 , , PUNCT eurjchem-32 123 57     SPACE eurjchem-32 123 58 methine methine ADJ eurjchem-32 123 59     SPACE eurjchem-32 123 60 proton proton NOUN eurjchem-32 123 61 , , PUNCT eurjchem-32 123 62     SPACE eurjchem-32 123 63 vinylic vinylic ADJ eurjchem-32 123 64     SPACE eurjchem-32 123 65 proton proton NOUN eurjchem-32 123 66     SPACE eurjchem-32 123 67 and and CCONJ eurjchem-32 123 68     SPACE eurjchem-32 123 69 eight eight NUM eurjchem-32 123 70     SPACE eurjchem-32 123 71 aromatic aromatic ADJ eurjchem-32 123 72     SPACE eurjchem-32 123 73 protons proton NOUN eurjchem-32 123 74 , , PUNCT eurjchem-32 123 75     SPACE eurjchem-32 123 76 respectively respectively ADV eurjchem-32 123 77 . . PUNCT eurjchem-32 123 78     SPACE eurjchem-32 123 79 also also ADV eurjchem-32 123 80     SPACE eurjchem-32 123 81 mass mass ADJ eurjchem-32 123 82     SPACE eurjchem-32 123 83 spectrum spectrum NOUN eurjchem-32 123 84     SPACE eurjchem-32 123 85 showed show VERB eurjchem-32 123 86     SPACE eurjchem-32 123 87 molecular molecular ADJ eurjchem-32 123 88     SPACE eurjchem-32 123 89 ion ion NOUN eurjchem-32 123 90     SPACE eurjchem-32 123 91 peak peak NOUN eurjchem-32 123 92     SPACE eurjchem-32 123 93 at at ADP eurjchem-32 123 94     SPACE eurjchem-32 123 95 m m PROPN eurjchem-32 123 96 / / PROPN eurjchem-32 123 97 z z NOUN eurjchem-32 123 98     SPACE eurjchem-32 123 99 343 343 NUM eurjchem-32 123 100     SPACE eurjchem-32 123 101 ( ( PUNCT eurjchem-32 123 102 m+ m+ NUM eurjchem-32 123 103 ) ) PUNCT eurjchem-32 123 104 . . PUNCT eurjchem-32 123 105     SPACE eurjchem-32 124 1 unexpectedly unexpectedly ADV eurjchem-32 124 2 , , PUNCT eurjchem-32 124 3     SPACE eurjchem-32 124 4 salicyaldehyde salicyaldehyde NOUN eurjchem-32 124 5     SPACE eurjchem-32 124 6 and and CCONJ eurjchem-32 124 7     SPACE eurjchem-32 124 8 2‐ 2‐ NUM eurjchem-32 124 9 hydroxy‐1‐naphthaldehyde hydroxy‐1‐naphthaldehyde NOUN eurjchem-32 124 10     SPACE eurjchem-32 124 11 reacted react VERB eurjchem-32 124 12     SPACE eurjchem-32 124 13 with with ADP eurjchem-32 124 14     SPACE eurjchem-32 124 15 4 4 NUM eurjchem-32 124 16     SPACE eurjchem-32 124 17 in in ADP eurjchem-32 124 18     SPACE eurjchem-32 124 19 refluxing refluxing NOUN eurjchem-32 124 20     SPACE eurjchem-32 124 21 ethanol ethanol NOUN eurjchem-32 124 22     SPACE eurjchem-32 124 23 containing contain VERB eurjchem-32 124 24     SPACE eurjchem-32 124 25 catalytic catalytic ADJ eurjchem-32 124 26     SPACE eurjchem-32 124 27 amounts amount NOUN eurjchem-32 124 28     SPACE eurjchem-32 124 29 of of ADP eurjchem-32 124 30     SPACE eurjchem-32 124 31 piperidine piperidine NOUN eurjchem-32 124 32     SPACE eurjchem-32 124 33 in in ADP eurjchem-32 124 34     SPACE eurjchem-32 124 35 a a DET eurjchem-32 124 36     SPACE eurjchem-32 124 37 different different ADJ eurjchem-32 124 38     SPACE eurjchem-32 124 39 way way NOUN eurjchem-32 124 40     SPACE eurjchem-32 124 41 to to ADP eurjchem-32 124 42     SPACE eurjchem-32 124 43 that that PRON eurjchem-32 124 44     SPACE eurjchem-32 124 45 with with ADP eurjchem-32 124 46     SPACE eurjchem-32 124 47 p‐chlorobenzaldehyde p‐chlorobenzaldehyde NOUN eurjchem-32 124 48 . . PUNCT eurjchem-32 124 49     SPACE eurjchem-32 124 50 therefore therefore ADV eurjchem-32 124 51 , , PUNCT eurjchem-32 124 52     SPACE eurjchem-32 124 53 it it PRON eurjchem-32 124 54     SPACE eurjchem-32 124 55 was be AUX eurjchem-32 124 56     SPACE eurjchem-32 124 57 found find VERB eurjchem-32 124 58     SPACE eurjchem-32 124 59 that that SCONJ eurjchem-32 124 60     SPACE eurjchem-32 124 61 refluxing refluxing NOUN eurjchem-32 124 62     SPACE eurjchem-32 124 63 of of ADP eurjchem-32 124 64     SPACE eurjchem-32 124 65 4 4 NUM eurjchem-32 124 66     SPACE eurjchem-32 124 67 with with ADP eurjchem-32 124 68     SPACE eurjchem-32 124 69 salicyaldehyde salicyaldehyde NOUN eurjchem-32 124 70     SPACE eurjchem-32 124 71 and/or and/or CCONJ eurjchem-32 124 72     SPACE eurjchem-32 124 73 2‐hydroxy‐1‐ 2‐hydroxy‐1‐ PROPN eurjchem-32 124 74 naphthaldehyde naphthaldehyde NOUN eurjchem-32 124 75     SPACE eurjchem-32 124 76 in in ADP eurjchem-32 124 77     SPACE eurjchem-32 124 78 ethanol ethanol NOUN eurjchem-32 124 79     SPACE eurjchem-32 124 80 in in ADP eurjchem-32 124 81     SPACE eurjchem-32 124 82 the the DET eurjchem-32 124 83     SPACE eurjchem-32 124 84 presence presence NOUN eurjchem-32 124 85     SPACE eurjchem-32 124 86 of of ADP eurjchem-32 124 87     SPACE eurjchem-32 124 88 piperidine piperidine NOUN eurjchem-32 124 89     SPACE eurjchem-32 124 90 afforded afford VERB eurjchem-32 124 91     SPACE eurjchem-32 124 92 the the DET eurjchem-32 124 93     SPACE eurjchem-32 124 94 corresponding corresponding ADJ eurjchem-32 124 95     SPACE eurjchem-32 124 96 chromenopyridine chromenopyridine NOUN eurjchem-32 124 97     SPACE eurjchem-32 124 98 and and CCONJ eurjchem-32 124 99     SPACE eurjchem-32 124 100 benzochromenopyridine benzochromenopyridine NOUN eurjchem-32 124 101     SPACE eurjchem-32 124 102 derivatives derivative NOUN eurjchem-32 124 103     SPACE eurjchem-32 124 104 16 16 NUM eurjchem-32 124 105     SPACE eurjchem-32 124 106 and and CCONJ eurjchem-32 124 107     SPACE eurjchem-32 124 108 17 17 NUM eurjchem-32 124 109 , , PUNCT eurjchem-32 124 110     SPACE eurjchem-32 124 111 respectively respectively ADV eurjchem-32 124 112     SPACE eurjchem-32 124 113 ( ( PUNCT eurjchem-32 124 114 scheme scheme NOUN eurjchem-32 124 115     SPACE eurjchem-32 124 116 8 8 NUM eurjchem-32 124 117     SPACE eurjchem-32 124 118 and and CCONJ eurjchem-32 124 119     SPACE eurjchem-32 124 120 9 9 NUM eurjchem-32 124 121 ) ) PUNCT eurjchem-32 124 122 . . PUNCT eurjchem-32 124 123     SPACE eurjchem-32 125 1 the the DET eurjchem-32 125 2     SPACE eurjchem-32 125 3 structures structure NOUN eurjchem-32 125 4     SPACE eurjchem-32 125 5 of of ADP eurjchem-32 125 6     SPACE eurjchem-32 125 7 2‐amino‐3‐(benzo[d]thiazol‐2‐yl)‐4h‐ 2‐amino‐3‐(benzo[d]thiazol‐2‐yl)‐4h‐ NOUN eurjchem-32 125 8 chromeno[2,3‐b]pyridin‐4‐one chromeno[2,3‐b]pyridin‐4‐one VERB eurjchem-32 125 9 , , PUNCT eurjchem-32 125 10     SPACE eurjchem-32 125 11 16 16 NUM eurjchem-32 125 12 , , PUNCT eurjchem-32 125 13     SPACE eurjchem-32 125 14 and and CCONJ eurjchem-32 125 15     SPACE eurjchem-32 125 16 2‐amino‐3‐(benzo[d 2‐amino‐3‐(benzo[d NOUN eurjchem-32 125 17 ] ] X eurjchem-32 125 18     SPACE eurjchem-32 125 19 thiazol‐2‐yl)‐benzo[5,6]‐4h‐chromeno[2,3‐b]pyridin‐4‐one thiazol‐2‐yl)‐benzo[5,6]‐4h‐chromeno[2,3‐b]pyridin‐4‐one NUM eurjchem-32 125 20     SPACE eurjchem-32 125 21 17 17 NUM eurjchem-32 125 22     SPACE eurjchem-32 125 23 were be AUX eurjchem-32 125 24     SPACE eurjchem-32 125 25 established establish VERB eurjchem-32 125 26     SPACE eurjchem-32 125 27 from from ADP eurjchem-32 125 28     SPACE eurjchem-32 125 29 their their PRON eurjchem-32 125 30     SPACE eurjchem-32 125 31 ir ir NOUN eurjchem-32 125 32 , , PUNCT eurjchem-32 125 33     SPACE eurjchem-32 125 34 1h 1h NUM eurjchem-32 125 35     SPACE eurjchem-32 125 36 nmr nmr NOUN eurjchem-32 125 37     SPACE eurjchem-32 125 38 and and CCONJ eurjchem-32 125 39     SPACE eurjchem-32 125 40 mass mass PROPN eurjchem-32 125 41     SPACE eurjchem-32 125 42 spectra spectra NOUN eurjchem-32 125 43 . . PUNCT eurjchem-32 125 44     SPACE eurjchem-32 126 1 the the DET eurjchem-32 126 2     SPACE eurjchem-32 126 3 mass mass ADJ eurjchem-32 126 4     SPACE eurjchem-32 126 5 spectrum spectrum NOUN eurjchem-32 126 6     SPACE eurjchem-32 126 7 of of ADP eurjchem-32 126 8     SPACE eurjchem-32 126 9 16 16 NUM eurjchem-32 126 10     SPACE eurjchem-32 126 11 showed show VERB eurjchem-32 126 12     SPACE eurjchem-32 126 13 molecular molecular ADJ eurjchem-32 126 14     SPACE eurjchem-32 126 15 ion ion NOUN eurjchem-32 126 16     SPACE eurjchem-32 126 17 peak peak NOUN eurjchem-32 126 18     SPACE eurjchem-32 126 19 at at ADP eurjchem-32 126 20     SPACE eurjchem-32 126 21 m m PROPN eurjchem-32 126 22 / / PROPN eurjchem-32 126 23 z z NOUN eurjchem-32 126 24     SPACE eurjchem-32 126 25 345 345 NUM eurjchem-32 126 26     SPACE eurjchem-32 126 27 ( ( PUNCT eurjchem-32 126 28 m+ m+ NOUN eurjchem-32 126 29 ) ) PUNCT eurjchem-32 126 30     SPACE eurjchem-32 126 31 ( ( PUNCT eurjchem-32 126 32 100 100 NUM eurjchem-32 126 33 % % NOUN eurjchem-32 126 34 ) ) PUNCT eurjchem-32 126 35 , , PUNCT eurjchem-32 126 36     SPACE eurjchem-32 126 37 while while SCONJ eurjchem-32 126 38     SPACE eurjchem-32 126 39 17 17 NUM eurjchem-32 126 40     SPACE eurjchem-32 126 41 showed show VERB eurjchem-32 126 42     SPACE eurjchem-32 126 43 the the DET eurjchem-32 126 44     SPACE eurjchem-32 126 45 molecular molecular ADJ eurjchem-32 126 46     SPACE eurjchem-32 126 47 ion ion NOUN eurjchem-32 126 48     SPACE eurjchem-32 126 49 peak peak NOUN eurjchem-32 126 50     SPACE eurjchem-32 126 51 at at ADP eurjchem-32 126 52     SPACE eurjchem-32 126 53 395 395 NUM eurjchem-32 126 54     SPACE eurjchem-32 126 55 m m PROPN eurjchem-32 126 56 / / PROPN eurjchem-32 126 57 z z NOUN eurjchem-32 126 58     SPACE eurjchem-32 126 59 ( ( PUNCT eurjchem-32 126 60 m+ m+ NUM eurjchem-32 126 61 , , PUNCT eurjchem-32 126 62     SPACE eurjchem-32 126 63 92 92 NUM eurjchem-32 126 64 % % NOUN eurjchem-32 126 65 ) ) PUNCT eurjchem-32 126 66 . . PUNCT eurjchem-32 126 67     SPACE eurjchem-32 127 1 the the DET eurjchem-32 127 2     SPACE eurjchem-32 127 3 ir ir PROPN eurjchem-32 127 4     SPACE eurjchem-32 127 5 spectra spectra NOUN eurjchem-32 127 6     SPACE eurjchem-32 127 7 of of ADP eurjchem-32 127 8     SPACE eurjchem-32 127 9 both both DET eurjchem-32 127 10     SPACE eurjchem-32 127 11 16 16 NUM eurjchem-32 127 12     SPACE eurjchem-32 127 13 and and CCONJ eurjchem-32 127 14     SPACE eurjchem-32 127 15 17 17 NUM eurjchem-32 127 16     SPACE eurjchem-32 127 17 showed show VERB eurjchem-32 127 18     SPACE eurjchem-32 127 19 the the DET eurjchem-32 127 20     SPACE eurjchem-32 127 21 absence absence NOUN eurjchem-32 127 22     SPACE eurjchem-32 127 23 of of ADP eurjchem-32 127 24     SPACE eurjchem-32 127 25 any any DET eurjchem-32 127 26     SPACE eurjchem-32 127 27 peak peak NOUN eurjchem-32 127 28     SPACE eurjchem-32 127 29 in in ADP eurjchem-32 127 30     SPACE eurjchem-32 127 31 the the DET eurjchem-32 127 32     SPACE eurjchem-32 127 33 region region NOUN eurjchem-32 127 34     SPACE eurjchem-32 127 35 of of ADP eurjchem-32 127 36     SPACE eurjchem-32 127 37 2180‐2250 2180‐2250 NUM eurjchem-32 127 38     SPACE eurjchem-32 127 39 cm‐1 cm‐1 NOUN eurjchem-32 127 40     SPACE eurjchem-32 127 41 and and CCONJ eurjchem-32 127 42     SPACE eurjchem-32 127 43 this this PRON eurjchem-32 127 44     SPACE eurjchem-32 127 45 confirms confirm VERB eurjchem-32 127 46     SPACE eurjchem-32 127 47 that that SCONJ eurjchem-32 127 48     SPACE eurjchem-32 127 49 both both DET eurjchem-32 127 50     SPACE eurjchem-32 127 51 two two NUM eurjchem-32 127 52     SPACE eurjchem-32 127 53 cn cn PROPN eurjchem-32 127 54     SPACE eurjchem-32 127 55 groups group NOUN eurjchem-32 127 56     SPACE eurjchem-32 127 57 were be AUX eurjchem-32 127 58     SPACE eurjchem-32 127 59 involved involve VERB eurjchem-32 127 60     SPACE eurjchem-32 127 61 in in ADP eurjchem-32 127 62     SPACE eurjchem-32 127 63 the the DET eurjchem-32 127 64     SPACE eurjchem-32 127 65 reaction reaction NOUN eurjchem-32 127 66 , , PUNCT eurjchem-32 127 67     SPACE eurjchem-32 127 68 also also ADV eurjchem-32 127 69     SPACE eurjchem-32 127 70 the the DET eurjchem-32 127 71     SPACE eurjchem-32 127 72 presence presence NOUN eurjchem-32 127 73     SPACE eurjchem-32 127 74 of of ADP eurjchem-32 127 75     SPACE eurjchem-32 127 76 two two NUM eurjchem-32 127 77     SPACE eurjchem-32 127 78 peaks peak NOUN eurjchem-32 127 79     SPACE eurjchem-32 127 80 in in ADP eurjchem-32 127 81     SPACE eurjchem-32 127 82 the the DET eurjchem-32 127 83     SPACE eurjchem-32 127 84 region region NOUN eurjchem-32 127 85     SPACE eurjchem-32 127 86 of of ADP eurjchem-32 127 87     SPACE eurjchem-32 127 88 3300‐ 3300‐ NUM eurjchem-32 127 89 3400 3400 NUM eurjchem-32 127 90     SPACE eurjchem-32 127 91 cm‐1due cm‐1due ADJ eurjchem-32 127 92     SPACE eurjchem-32 127 93 to to ADP eurjchem-32 127 94     SPACE eurjchem-32 127 95 the the DET eurjchem-32 127 96     SPACE eurjchem-32 127 97 nh2 nh2 NOUN eurjchem-32 127 98     SPACE eurjchem-32 127 99 group group NOUN eurjchem-32 127 100 . . PUNCT eurjchem-32 127 101     SPACE eurjchem-32 127 102 1h 1h NUM eurjchem-32 127 103     SPACE eurjchem-32 127 104 nmr nmr NOUN eurjchem-32 127 105     SPACE eurjchem-32 127 106 spectrum spectrum NOUN eurjchem-32 127 107     SPACE eurjchem-32 127 108 of of ADP eurjchem-32 127 109     SPACE eurjchem-32 127 110 16 16 NUM eurjchem-32 127 111     SPACE eurjchem-32 127 112 showed show VERB eurjchem-32 127 113     SPACE eurjchem-32 127 114 a a DET eurjchem-32 127 115     SPACE eurjchem-32 127 116 multiplet multiplet NOUN eurjchem-32 127 117     SPACE eurjchem-32 127 118 signal signal NOUN eurjchem-32 127 119     SPACE eurjchem-32 127 120 in in ADP eurjchem-32 127 121     SPACE eurjchem-32 127 122 the the DET eurjchem-32 127 123     SPACE eurjchem-32 127 124 region region NOUN eurjchem-32 127 125     SPACE eurjchem-32 127 126 of of ADP eurjchem-32 127 127     SPACE eurjchem-32 127 128 δ δ PROPN eurjchem-32 127 129     SPACE eurjchem-32 127 130 6.93‐8.16 6.93‐8.16 NOUN eurjchem-32 127 131     SPACE eurjchem-32 127 132 ppm ppm NOUN eurjchem-32 127 133     SPACE eurjchem-32 127 134 due due ADJ eurjchem-32 127 135     SPACE eurjchem-32 127 136 to to ADP eurjchem-32 127 137     SPACE eurjchem-32 127 138 eight eight NUM eurjchem-32 127 139     SPACE eurjchem-32 127 140 aromatic aromatic ADJ eurjchem-32 127 141     SPACE eurjchem-32 127 142 protons proton NOUN eurjchem-32 127 143 , , PUNCT eurjchem-32 127 144     SPACE eurjchem-32 127 145 in in ADP eurjchem-32 127 146     SPACE eurjchem-32 127 147 addition addition NOUN eurjchem-32 127 148     SPACE eurjchem-32 127 149 to to ADP eurjchem-32 127 150     SPACE eurjchem-32 127 151 two two NUM eurjchem-32 127 152     SPACE eurjchem-32 127 153 singlet singlet NOUN eurjchem-32 127 154     SPACE eurjchem-32 127 155 signals signal NOUN eurjchem-32 127 156     SPACE eurjchem-32 127 157 at at ADP eurjchem-32 127 158     SPACE eurjchem-32 127 159 δ δ PROPN eurjchem-32 127 160     SPACE eurjchem-32 127 161 8.60 8.60 NUM eurjchem-32 127 162     SPACE eurjchem-32 127 163 and and CCONJ eurjchem-32 127 164     SPACE eurjchem-32 127 165 8.77 8.77 NUM eurjchem-32 127 166     SPACE eurjchem-32 127 167 ppm ppm NOUN eurjchem-32 127 168     SPACE eurjchem-32 127 169 due due ADJ eurjchem-32 127 170     SPACE eurjchem-32 127 171 to to PART eurjchem-32 127 172     SPACE eurjchem-32 127 173 nh2 nh2 NOUN eurjchem-32 127 174     SPACE eurjchem-32 127 175 protons proton NOUN eurjchem-32 127 176     SPACE eurjchem-32 127 177 and and CCONJ eurjchem-32 127 178     SPACE eurjchem-32 127 179 c4‐h c4‐h NOUN eurjchem-32 127 180     SPACE eurjchem-32 127 181 in in ADP eurjchem-32 127 182     SPACE eurjchem-32 127 183 the the DET eurjchem-32 127 184     SPACE eurjchem-32 127 185 pyran pyran ADJ eurjchem-32 127 186     SPACE eurjchem-32 127 187 ring ring NOUN eurjchem-32 127 188 , , PUNCT eurjchem-32 127 189     SPACE eurjchem-32 127 190 respectively respectively ADV eurjchem-32 127 191 . . PUNCT eurjchem-32 127 192     SPACE eurjchem-32 127 193 on on ADP eurjchem-32 127 194     SPACE eurjchem-32 127 195 the the DET eurjchem-32 127 196     SPACE eurjchem-32 127 197 other other ADJ eurjchem-32 127 198     SPACE eurjchem-32 127 199 hand hand NOUN eurjchem-32 127 200 , , PUNCT eurjchem-32 127 201     SPACE eurjchem-32 127 202 1h 1h NUM eurjchem-32 127 203     SPACE eurjchem-32 127 204 nmr nmr NOUN eurjchem-32 127 205     SPACE eurjchem-32 127 206 of of ADP eurjchem-32 127 207     SPACE eurjchem-32 127 208 compound compound NOUN eurjchem-32 127 209     SPACE eurjchem-32 127 210 17 17 NUM eurjchem-32 127 211     SPACE eurjchem-32 127 212 could could AUX eurjchem-32 127 213     SPACE eurjchem-32 127 214 not not PART eurjchem-32 127 215     SPACE eurjchem-32 127 216 be be AUX eurjchem-32 127 217     SPACE eurjchem-32 127 218 evaluated evaluate VERB eurjchem-32 127 219     SPACE eurjchem-32 127 220 due due ADJ eurjchem-32 127 221     SPACE eurjchem-32 127 222 to to ADP eurjchem-32 127 223     SPACE eurjchem-32 127 224 its its PRON eurjchem-32 127 225     SPACE eurjchem-32 127 226 insolubility insolubility NOUN eurjchem-32 127 227     SPACE eurjchem-32 127 228 in in ADP eurjchem-32 127 229     SPACE eurjchem-32 127 230 all all DET eurjchem-32 127 231     SPACE eurjchem-32 127 232 possible possible ADJ eurjchem-32 127 233     SPACE eurjchem-32 127 234 solvents solvent NOUN eurjchem-32 127 235 . . PUNCT eurjchem-32 127 236     SPACE eurjchem-32 128 1 these these DET eurjchem-32 128 2     SPACE eurjchem-32 128 3 above above ADP eurjchem-32 128 4     SPACE eurjchem-32 128 5 results result NOUN eurjchem-32 128 6     SPACE eurjchem-32 128 7 were be AUX eurjchem-32 128 8     SPACE eurjchem-32 128 9 found find VERB eurjchem-32 128 10     SPACE eurjchem-32 128 11 in in ADP eurjchem-32 128 12     SPACE eurjchem-32 128 13 complete complete ADJ eurjchem-32 128 14     SPACE eurjchem-32 128 15 agreement agreement NOUN eurjchem-32 128 16     SPACE eurjchem-32 128 17 with with ADP eurjchem-32 128 18     SPACE eurjchem-32 128 19 a a PRON eurjchem-32 128 20     SPACE eurjchem-32 128 21 previously previously ADV eurjchem-32 128 22     SPACE eurjchem-32 128 23 reported report VERB eurjchem-32 128 24     SPACE eurjchem-32 128 25 work work NOUN eurjchem-32 128 26     SPACE eurjchem-32 129 1 [ [ X eurjchem-32 129 2 22,23 22,23 NOUN eurjchem-32 129 3 ] ] X eurjchem-32 129 4 . . PUNCT eurjchem-32 129 5     SPACE eurjchem-32 130 1 moreover moreover ADV eurjchem-32 130 2 , , PUNCT eurjchem-32 130 3     SPACE eurjchem-32 130 4 treatment treatment NOUN eurjchem-32 130 5     SPACE eurjchem-32 130 6 of of ADP eurjchem-32 130 7     SPACE eurjchem-32 130 8 4 4 NUM eurjchem-32 130 9     SPACE eurjchem-32 130 10 with with ADP eurjchem-32 130 11     SPACE eurjchem-32 130 12 hydroxylamine hydroxylamine NOUN eurjchem-32 130 13     SPACE eurjchem-32 130 14 hydrochloride hydrochloride NOUN eurjchem-32 130 15     SPACE eurjchem-32 130 16 afforded afford VERB eurjchem-32 130 17     SPACE eurjchem-32 130 18 2‐ 2‐ NUM eurjchem-32 130 19 ( ( PUNCT eurjchem-32 130 20 5‐aminoisoxazol‐3‐yl)‐2‐(benzo[d]thiazol‐2‐yl)‐acetonitrile 5‐aminoisoxazol‐3‐yl)‐2‐(benzo[d]thiazol‐2‐yl)‐acetonitrile NOUN eurjchem-32 130 21     SPACE eurjchem-32 130 22 18 18 NUM eurjchem-32 130 23     SPACE eurjchem-32 130 24 in in ADP eurjchem-32 130 25     SPACE eurjchem-32 130 26 high high ADJ eurjchem-32 130 27     SPACE eurjchem-32 130 28 yield yield NOUN eurjchem-32 130 29     SPACE eurjchem-32 130 30 ( ( PUNCT eurjchem-32 130 31 scheme scheme NOUN eurjchem-32 130 32     SPACE eurjchem-32 130 33 10 10 NUM eurjchem-32 130 34 ) ) PUNCT eurjchem-32 130 35 . . PUNCT eurjchem-32 130 36     SPACE eurjchem-32 131 1 structure structure NOUN eurjchem-32 131 2     SPACE eurjchem-32 131 3 18 18 NUM eurjchem-32 131 4     SPACE eurjchem-32 131 5 was be AUX eurjchem-32 131 6     SPACE eurjchem-32 131 7 suggested suggest VERB eurjchem-32 131 8     SPACE eurjchem-32 131 9 for for ADP eurjchem-32 131 10     SPACE eurjchem-32 131 11 this this DET eurjchem-32 131 12     SPACE eurjchem-32 131 13 product product NOUN eurjchem-32 131 14     SPACE eurjchem-32 131 15 based base VERB eurjchem-32 131 16     SPACE eurjchem-32 131 17 on on ADP eurjchem-32 131 18     SPACE eurjchem-32 131 19 analytical analytical ADJ eurjchem-32 131 20     SPACE eurjchem-32 131 21 and and CCONJ eurjchem-32 131 22     SPACE eurjchem-32 131 23 spectral spectral ADJ eurjchem-32 131 24     SPACE eurjchem-32 131 25 data datum NOUN eurjchem-32 131 26 . . PUNCT eurjchem-32 131 27     SPACE eurjchem-32 132 1 thus thus ADV eurjchem-32 132 2     SPACE eurjchem-32 132 3 the the DET eurjchem-32 132 4     SPACE eurjchem-32 132 5 mass mass ADJ eurjchem-32 132 6     SPACE eurjchem-32 132 7 spectrum spectrum NOUN eurjchem-32 132 8     SPACE eurjchem-32 132 9 of of ADP eurjchem-32 132 10     SPACE eurjchem-32 132 11 this this DET eurjchem-32 132 12     SPACE eurjchem-32 132 13 product product NOUN eurjchem-32 132 14     SPACE eurjchem-32 132 15 showed show VERB eurjchem-32 132 16     SPACE eurjchem-32 132 17 the the DET eurjchem-32 132 18     SPACE eurjchem-32 132 19 molecular molecular ADJ eurjchem-32 132 20     SPACE eurjchem-32 132 21 ion ion NOUN eurjchem-32 132 22     SPACE eurjchem-32 132 23 peak peak NOUN eurjchem-32 132 24     SPACE eurjchem-32 132 25 at at ADP eurjchem-32 132 26     SPACE eurjchem-32 132 27 m m PROPN eurjchem-32 132 28 / / PROPN eurjchem-32 132 29 z z NOUN eurjchem-32 132 30     SPACE eurjchem-32 132 31 256 256 NUM eurjchem-32 132 32     SPACE eurjchem-32 132 33 ( ( PUNCT eurjchem-32 132 34 m+ m+ NOUN eurjchem-32 132 35 ) ) PUNCT eurjchem-32 132 36 , , PUNCT eurjchem-32 132 37     SPACE eurjchem-32 132 38 201 201 NUM eurjchem-32 132 39 , , PUNCT eurjchem-32 132 40     SPACE eurjchem-32 132 41 174 174 NUM eurjchem-32 132 42     SPACE eurjchem-32 132 43 ( ( PUNCT eurjchem-32 132 44 100 100 NUM eurjchem-32 132 45 % % NOUN eurjchem-32 132 46 ) ) PUNCT eurjchem-32 132 47 . . PUNCT eurjchem-32 132 48     SPACE eurjchem-32 133 1 the the DET eurjchem-32 133 2     SPACE eurjchem-32 133 3 ir ir NOUN eurjchem-32 133 4     SPACE eurjchem-32 133 5 spectrum spectrum NOUN eurjchem-32 133 6     SPACE eurjchem-32 133 7 revealed reveal VERB eurjchem-32 133 8     SPACE eurjchem-32 133 9 absorption absorption NOUN eurjchem-32 133 10     SPACE eurjchem-32 133 11 bands band NOUN eurjchem-32 133 12     SPACE eurjchem-32 133 13 at at ADP eurjchem-32 133 14     SPACE eurjchem-32 133 15 3325 3325 NUM eurjchem-32 133 16 , , PUNCT eurjchem-32 133 17     SPACE eurjchem-32 133 18 3309 3309 NUM eurjchem-32 133 19     SPACE eurjchem-32 133 20 cm‐1 cm‐1 NOUN eurjchem-32 133 21     SPACE eurjchem-32 133 22 ( ( PUNCT eurjchem-32 133 23 nh2 nh2 PROPN eurjchem-32 133 24 ) ) PUNCT eurjchem-32 133 25 , , PUNCT eurjchem-32 133 26     SPACE eurjchem-32 133 27 2199 2199 NUM eurjchem-32 133 28     SPACE eurjchem-32 133 29 cm‐1 cm‐1 NOUN eurjchem-32 133 30     SPACE eurjchem-32 133 31 ( ( PUNCT eurjchem-32 133 32 cn cn PROPN eurjchem-32 133 33 ) ) PUNCT eurjchem-32 133 34 . . PUNCT eurjchem-32 133 35     SPACE eurjchem-32 134 1 the the DET eurjchem-32 134 2     SPACE eurjchem-32 134 3 1h 1h NUM eurjchem-32 134 4     SPACE eurjchem-32 134 5 nmr nmr NOUN eurjchem-32 134 6     SPACE eurjchem-32 134 7 ( ( PUNCT eurjchem-32 134 8 dmso dmso NOUN eurjchem-32 134 9 ) ) PUNCT eurjchem-32 134 10     SPACE eurjchem-32 134 11 spectrum spectrum NOUN eurjchem-32 134 12     SPACE eurjchem-32 134 13 revealed reveal VERB eurjchem-32 134 14     SPACE eurjchem-32 134 15 signals signal NOUN eurjchem-32 134 16     SPACE eurjchem-32 134 17 at at ADP eurjchem-32 134 18     SPACE eurjchem-32 134 19 δ δ PROPN eurjchem-32 134 20     SPACE eurjchem-32 134 21 7.2 7.2 NUM eurjchem-32 134 22 , , PUNCT eurjchem-32 134 23     SPACE eurjchem-32 134 24 7.3‐8.1 7.3‐8.1 NOUN eurjchem-32 134 25     SPACE eurjchem-32 134 26 and and CCONJ eurjchem-32 134 27     SPACE eurjchem-32 134 28 8.19 8.19 NUM eurjchem-32 134 29     SPACE eurjchem-32 134 30 ppm ppm NOUN eurjchem-32 134 31     SPACE eurjchem-32 134 32 due due ADJ eurjchem-32 134 33     SPACE eurjchem-32 134 34 to to PART eurjchem-32 134 35     SPACE eurjchem-32 134 36 nh2 nh2 PROPN eurjchem-32 134 37 , , PUNCT eurjchem-32 134 38     SPACE eurjchem-32 134 39 the the DET eurjchem-32 134 40     SPACE eurjchem-32 134 41 aromatic aromatic NOUN eurjchem-32 134 42     SPACE eurjchem-32 134 43 and and CCONJ eurjchem-32 134 44     SPACE eurjchem-32 134 45 the the DET eurjchem-32 134 46     SPACE eurjchem-32 134 47 cyclic cyclic ADJ eurjchem-32 134 48     SPACE eurjchem-32 134 49 methine methine ADJ eurjchem-32 134 50     SPACE eurjchem-32 134 51 protons proton NOUN eurjchem-32 134 52 , , PUNCT eurjchem-32 134 53     SPACE eurjchem-32 134 54 respectively respectively ADV eurjchem-32 134 55 , , PUNCT eurjchem-32 134 56     SPACE eurjchem-32 134 57 and and CCONJ eurjchem-32 134 58     SPACE eurjchem-32 134 59 at at ADP eurjchem-32 134 60     SPACE eurjchem-32 134 61 δ δ PROPN eurjchem-32 134 62     SPACE eurjchem-32 134 63 4.25 4.25 NUM eurjchem-32 134 64     SPACE eurjchem-32 134 65 ppm ppm NOUN eurjchem-32 134 66     SPACE eurjchem-32 134 67 due due ADJ eurjchem-32 134 68     SPACE eurjchem-32 134 69 to to ADP eurjchem-32 134 70     SPACE eurjchem-32 134 71 the the DET eurjchem-32 134 72     SPACE eurjchem-32 134 73 ch ch NOUN eurjchem-32 134 74     SPACE eurjchem-32 134 75 proton proton NOUN eurjchem-32 134 76 . . PUNCT eurjchem-32 134 77     SPACE eurjchem-32 135 1 treatment treatment NOUN eurjchem-32 135 2     SPACE eurjchem-32 135 3 of of ADP eurjchem-32 135 4     SPACE eurjchem-32 135 5 4 4 NUM eurjchem-32 135 6     SPACE eurjchem-32 135 7 with with ADP eurjchem-32 135 8     SPACE eurjchem-32 135 9 hydrazine hydrazine NOUN eurjchem-32 135 10     SPACE eurjchem-32 135 11 hydrate hydrate NOUN eurjchem-32 135 12     SPACE eurjchem-32 135 13 in in ADP eurjchem-32 135 14     SPACE eurjchem-32 135 15 refluxing refluxing NOUN eurjchem-32 135 16     SPACE eurjchem-32 135 17 ethanol ethanol NOUN eurjchem-32 135 18     SPACE eurjchem-32 135 19 afforded afford VERB eurjchem-32 135 20     SPACE eurjchem-32 135 21 3,7‐diamino‐4‐ 3,7‐diamino‐4‐ NUM eurjchem-32 135 22 ( ( PUNCT eurjchem-32 135 23 benzo[d]thiazol‐2‐yl)‐4h‐1,2‐diazepin‐5(6h)‐one benzo[d]thiazol‐2‐yl)‐4h‐1,2‐diazepin‐5(6h)‐one NOUN eurjchem-32 135 24 , , PUNCT eurjchem-32 135 25     SPACE eurjchem-32 135 26 19 19 NUM eurjchem-32 135 27     SPACE eurjchem-32 135 28 ( ( PUNCT eurjchem-32 135 29 scheme scheme NOUN eurjchem-32 135 30     SPACE eurjchem-32 135 31 10 10 NUM eurjchem-32 135 32 ) ) PUNCT eurjchem-32 135 33 . . PUNCT eurjchem-32 135 34     SPACE eurjchem-32 136 1 the the DET eurjchem-32 136 2     SPACE eurjchem-32 136 3 ir ir NOUN eurjchem-32 136 4     SPACE eurjchem-32 136 5 spectrum spectrum NOUN eurjchem-32 136 6     SPACE eurjchem-32 136 7 of of ADP eurjchem-32 136 8     SPACE eurjchem-32 136 9 19 19 NUM eurjchem-32 136 10     SPACE eurjchem-32 136 11 showed show VERB eurjchem-32 136 12     SPACE eurjchem-32 136 13 the the DET eurjchem-32 136 14     SPACE eurjchem-32 136 15 absence absence NOUN eurjchem-32 136 16     SPACE eurjchem-32 136 17 of of ADP eurjchem-32 136 18     SPACE eurjchem-32 136 19 peaks peak NOUN eurjchem-32 136 20     SPACE eurjchem-32 136 21 in in ADP eurjchem-32 136 22     SPACE eurjchem-32 136 23 the the DET eurjchem-32 136 24     SPACE eurjchem-32 136 25 region region NOUN eurjchem-32 136 26     SPACE eurjchem-32 136 27 of of ADP eurjchem-32 136 28     SPACE eurjchem-32 136 29 2180‐2250 2180‐2250 NUM eurjchem-32 136 30     SPACE eurjchem-32 136 31 cm‐1 cm‐1 NOUN eurjchem-32 136 32     SPACE eurjchem-32 136 33 due due ADJ eurjchem-32 136 34     SPACE eurjchem-32 136 35 to to ADP eurjchem-32 136 36     SPACE eurjchem-32 136 37 the the DET eurjchem-32 136 38     SPACE eurjchem-32 136 39 cn cn PROPN eurjchem-32 136 40     SPACE eurjchem-32 136 41 group group NOUN eurjchem-32 136 42 , , PUNCT eurjchem-32 136 43     SPACE eurjchem-32 136 44 which which PRON eurjchem-32 136 45     SPACE eurjchem-32 136 46 indicates indicate VERB eurjchem-32 136 47     SPACE eurjchem-32 136 48 that that SCONJ eurjchem-32 136 49     SPACE eurjchem-32 136 50 both both DET eurjchem-32 136 51     SPACE eurjchem-32 136 52 the the DET eurjchem-32 136 53     SPACE eurjchem-32 136 54 cn cn PROPN eurjchem-32 136 55     SPACE eurjchem-32 136 56 groups group NOUN eurjchem-32 136 57     SPACE eurjchem-32 136 58 were be AUX eurjchem-32 136 59     SPACE eurjchem-32 136 60 involved involve VERB eurjchem-32 136 61     SPACE eurjchem-32 136 62 in in ADP eurjchem-32 136 63     SPACE eurjchem-32 136 64 this this DET eurjchem-32 136 65     SPACE eurjchem-32 136 66 reaction reaction NOUN eurjchem-32 136 67 . . PUNCT eurjchem-32 136 68     SPACE eurjchem-32 137 1 the the DET eurjchem-32 137 2     SPACE eurjchem-32 137 3 mass mass NOUN eurjchem-32 137 4     SPACE eurjchem-32 137 5 spectrum spectrum NOUN eurjchem-32 137 6     SPACE eurjchem-32 137 7 of of ADP eurjchem-32 137 8     SPACE eurjchem-32 137 9 19 19 NUM eurjchem-32 137 10     SPACE eurjchem-32 137 11 gave give VERB eurjchem-32 137 12     SPACE eurjchem-32 137 13 the the DET eurjchem-32 137 14     SPACE eurjchem-32 137 15 molecular molecular ADJ eurjchem-32 137 16     SPACE eurjchem-32 137 17 ion ion NOUN eurjchem-32 137 18     SPACE eurjchem-32 137 19 peak peak NOUN eurjchem-32 137 20     SPACE eurjchem-32 137 21 at at ADP eurjchem-32 137 22     SPACE eurjchem-32 137 23 m m PROPN eurjchem-32 137 24 / / PROPN eurjchem-32 137 25 z z NOUN eurjchem-32 137 26     SPACE eurjchem-32 137 27 273 273 NUM eurjchem-32 137 28     SPACE eurjchem-32 137 29 ( ( PUNCT eurjchem-32 137 30 m+ m+ NUM eurjchem-32 137 31 ) ) PUNCT eurjchem-32 137 32 . . PUNCT eurjchem-32 137 33     SPACE eurjchem-32 138 1 several several ADJ eurjchem-32 138 2     SPACE eurjchem-32 138 3 isomeric isomeric ADJ eurjchem-32 138 4     SPACE eurjchem-32 138 5 structures structure NOUN eurjchem-32 138 6     SPACE eurjchem-32 138 7 of of ADP eurjchem-32 138 8     SPACE eurjchem-32 138 9 19 19 NUM eurjchem-32 138 10     SPACE eurjchem-32 138 11 were be AUX eurjchem-32 138 12     SPACE eurjchem-32 138 13 possible possible ADJ eurjchem-32 138 14     SPACE eurjchem-32 138 15 but but CCONJ eurjchem-32 138 16     SPACE eurjchem-32 138 17 the the DET eurjchem-32 138 18     SPACE eurjchem-32 138 19 actual actual ADJ eurjchem-32 138 20     SPACE eurjchem-32 138 21 isomeric isomeric ADJ eurjchem-32 138 22     SPACE eurjchem-32 138 23 form form NOUN eurjchem-32 138 24     SPACE eurjchem-32 138 25 was be AUX eurjchem-32 138 26     SPACE eurjchem-32 138 27 confirmed confirm VERB eurjchem-32 138 28     SPACE eurjchem-32 138 29 from from ADP eurjchem-32 138 30     SPACE eurjchem-32 138 31 its its PRON eurjchem-32 138 32     SPACE eurjchem-32 138 33 1h 1h NUM eurjchem-32 138 34     SPACE eurjchem-32 138 35 nmr nmr NOUN eurjchem-32 138 36     SPACE eurjchem-32 138 37 which which PRON eurjchem-32 138 38     SPACE eurjchem-32 138 39 showed show VERB eurjchem-32 138 40     SPACE eurjchem-32 138 41 doublet doublet PROPN eurjchem-32 138 42     SPACE eurjchem-32 138 43 of of ADP eurjchem-32 138 44     SPACE eurjchem-32 138 45 doublet doublet PROPN eurjchem-32 138 46     SPACE eurjchem-32 138 47 signal signal NOUN eurjchem-32 138 48     SPACE eurjchem-32 138 49 at at ADP eurjchem-32 138 50     SPACE eurjchem-32 138 51 δ δ PROPN eurjchem-32 138 52     SPACE eurjchem-32 138 53 2.4:2.5 2.4:2.5 NUM eurjchem-32 138 54     SPACE eurjchem-32 138 55 ppm ppm NOUN eurjchem-32 138 56     SPACE eurjchem-32 138 57 due due ADJ eurjchem-32 138 58     SPACE eurjchem-32 138 59 to to ADP eurjchem-32 138 60     SPACE eurjchem-32 138 61 ch2 ch2 PROPN eurjchem-32 138 62     SPACE eurjchem-32 138 63 protons proton NOUN eurjchem-32 138 64 , , PUNCT eurjchem-32 138 65     SPACE eurjchem-32 138 66 at at ADP eurjchem-32 138 67     SPACE eurjchem-32 138 68 δ δ PROPN eurjchem-32 138 69     SPACE eurjchem-32 138 70 3.76 3.76 NUM eurjchem-32 138 71     SPACE eurjchem-32 138 72 ppm ppm NOUN eurjchem-32 138 73     SPACE eurjchem-32 138 74 due due ADJ eurjchem-32 138 75     SPACE eurjchem-32 138 76 to to ADP eurjchem-32 138 77     SPACE eurjchem-32 138 78 the the DET eurjchem-32 138 79     SPACE eurjchem-32 138 80 ch ch NOUN eurjchem-32 138 81     SPACE eurjchem-32 138 82 proton proton NOUN eurjchem-32 138 83     SPACE eurjchem-32 138 84 beside beside ADP eurjchem-32 138 85     SPACE eurjchem-32 138 86 the the DET eurjchem-32 138 87     SPACE eurjchem-32 138 88 fadda fadda NOUN eurjchem-32 138 89     SPACE eurjchem-32 138 90 et et PROPN eurjchem-32 138 91     SPACE eurjchem-32 138 92 al al PROPN eurjchem-32 138 93 . . PROPN eurjchem-32 138 94     SPACE eurjchem-32 138 95 / / SYM eurjchem-32 138 96     SPACE eurjchem-32 138 97 european european ADJ eurjchem-32 138 98     SPACE eurjchem-32 138 99 journal journal NOUN eurjchem-32 138 100     SPACE eurjchem-32 138 101 of of ADP eurjchem-32 138 102     SPACE eurjchem-32 138 103 chemistry chemistry NOUN eurjchem-32 138 104     SPACE eurjchem-32 138 105 1 1 NUM eurjchem-32 138 106     SPACE eurjchem-32 138 107 ( ( PUNCT eurjchem-32 138 108 2 2 NUM eurjchem-32 138 109 ) ) PUNCT eurjchem-32 138 110     SPACE eurjchem-32 138 111 ( ( PUNCT eurjchem-32 138 112 2010 2010 NUM eurjchem-32 138 113 ) ) PUNCT eurjchem-32 138 114     SPACE eurjchem-32 138 115 90­95 90­95 NUM eurjchem-32 138 116     SPACE eurjchem-32 138 117 95 95 NUM eurjchem-32 138 118     SPACE eurjchem-32 138 119 multiplet multiplet NOUN eurjchem-32 138 120     SPACE eurjchem-32 138 121 signals signal NOUN eurjchem-32 138 122     SPACE eurjchem-32 138 123 at at ADP eurjchem-32 138 124     SPACE eurjchem-32 138 125 δ δ PROPN eurjchem-32 138 126     SPACE eurjchem-32 138 127 7.26‐8.12 7.26‐8.12 NUM eurjchem-32 138 128     SPACE eurjchem-32 138 129 ppm ppm NOUN eurjchem-32 138 130     SPACE eurjchem-32 138 131 due due ADJ eurjchem-32 138 132     SPACE eurjchem-32 138 133 to to ADP eurjchem-32 138 134     SPACE eurjchem-32 138 135 four four NUM eurjchem-32 138 136     SPACE eurjchem-32 138 137 aromatic aromatic ADJ eurjchem-32 138 138     SPACE eurjchem-32 138 139 protons proton NOUN eurjchem-32 138 140     SPACE eurjchem-32 138 141 and and CCONJ eurjchem-32 138 142     SPACE eurjchem-32 138 143 at at ADP eurjchem-32 138 144     SPACE eurjchem-32 138 145 δ δ PROPN eurjchem-32 138 146     SPACE eurjchem-32 138 147 8.51 8.51 NUM eurjchem-32 138 148     SPACE eurjchem-32 138 149 ppm ppm NOUN eurjchem-32 138 150     SPACE eurjchem-32 138 151 ( ( PUNCT eurjchem-32 138 152 s s PROPN eurjchem-32 138 153 , , PUNCT eurjchem-32 138 154     SPACE eurjchem-32 138 155 4h 4h NOUN eurjchem-32 138 156 , , PUNCT eurjchem-32 138 157     SPACE eurjchem-32 138 158 2nh2 2nh2 NUM eurjchem-32 138 159 ) ) PUNCT eurjchem-32 138 160 . . PUNCT eurjchem-32 138 161     SPACE eurjchem-32 139 1 compound compound NOUN eurjchem-32 139 2     SPACE eurjchem-32 139 3 4 4 NUM eurjchem-32 139 4     SPACE eurjchem-32 139 5 was be AUX eurjchem-32 139 6     SPACE eurjchem-32 139 7 also also ADV eurjchem-32 139 8     SPACE eurjchem-32 139 9 used use VERB eurjchem-32 139 10     SPACE eurjchem-32 139 11 as as ADP eurjchem-32 139 12     SPACE eurjchem-32 139 13 a a DET eurjchem-32 139 14     SPACE eurjchem-32 139 15 precursor precursor NOUN eurjchem-32 139 16     SPACE eurjchem-32 139 17 for for ADP eurjchem-32 139 18     SPACE eurjchem-32 139 19 the the DET eurjchem-32 139 20     SPACE eurjchem-32 139 21 synthesis synthesis NOUN eurjchem-32 139 22     SPACE eurjchem-32 139 23 of of ADP eurjchem-32 139 24     SPACE eurjchem-32 139 25 the the DET eurjchem-32 139 26     SPACE eurjchem-32 139 27 pyridine pyridine NOUN eurjchem-32 139 28     SPACE eurjchem-32 139 29 ring ring NOUN eurjchem-32 139 30 . . PUNCT eurjchem-32 139 31     SPACE eurjchem-32 140 1 thus thus ADV eurjchem-32 140 2 , , PUNCT eurjchem-32 140 3     SPACE eurjchem-32 140 4 treatment treatment NOUN eurjchem-32 140 5     SPACE eurjchem-32 140 6 of of ADP eurjchem-32 140 7     SPACE eurjchem-32 140 8 4 4 NUM eurjchem-32 140 9     SPACE eurjchem-32 140 10 with with ADP eurjchem-32 140 11     SPACE eurjchem-32 140 12 benzal benzal NOUN eurjchem-32 140 13     SPACE eurjchem-32 140 14 acetophenone acetophenone NOUN eurjchem-32 140 15     SPACE eurjchem-32 140 16 20 20 NUM eurjchem-32 140 17     SPACE eurjchem-32 140 18 in in ADP eurjchem-32 140 19     SPACE eurjchem-32 140 20 refluxing refluxing NOUN eurjchem-32 140 21     SPACE eurjchem-32 140 22 ethanol ethanol NOUN eurjchem-32 140 23     SPACE eurjchem-32 140 24 containing contain VERB eurjchem-32 140 25     SPACE eurjchem-32 140 26 catalytic catalytic ADJ eurjchem-32 140 27     SPACE eurjchem-32 140 28 amounts amount NOUN eurjchem-32 140 29     SPACE eurjchem-32 140 30 of of ADP eurjchem-32 140 31     SPACE eurjchem-32 140 32 tea tea NOUN eurjchem-32 140 33     SPACE eurjchem-32 140 34 afforded afford VERB eurjchem-32 140 35     SPACE eurjchem-32 140 36 compound compound NOUN eurjchem-32 140 37     SPACE eurjchem-32 140 38 21a 21a NOUN eurjchem-32 140 39     SPACE eurjchem-32 140 40 or or CCONJ eurjchem-32 140 41     SPACE eurjchem-32 140 42 its its PRON eurjchem-32 140 43     SPACE eurjchem-32 140 44 tautomer tautomer NOUN eurjchem-32 140 45     SPACE eurjchem-32 140 46 21b 21b NOUN eurjchem-32 140 47     SPACE eurjchem-32 140 48 ( ( PUNCT eurjchem-32 140 49 scheme scheme NOUN eurjchem-32 140 50     SPACE eurjchem-32 140 51 11 11 NUM eurjchem-32 140 52 ) ) PUNCT eurjchem-32 140 53 . . PUNCT eurjchem-32 140 54     SPACE eurjchem-32 141 1 the the DET eurjchem-32 141 2     SPACE eurjchem-32 141 3 structure structure NOUN eurjchem-32 141 4     SPACE eurjchem-32 141 5 of of ADP eurjchem-32 141 6     SPACE eurjchem-32 141 7 the the DET eurjchem-32 141 8     SPACE eurjchem-32 141 9 obtained obtain VERB eurjchem-32 141 10     SPACE eurjchem-32 141 11 product product NOUN eurjchem-32 141 12     SPACE eurjchem-32 141 13 was be AUX eurjchem-32 141 14     SPACE eurjchem-32 141 15 confirmed confirm VERB eurjchem-32 141 16     SPACE eurjchem-32 141 17 by by ADP eurjchem-32 141 18     SPACE eurjchem-32 141 19 its its PRON eurjchem-32 141 20     SPACE eurjchem-32 141 21 ir ir NOUN eurjchem-32 141 22 , , PUNCT eurjchem-32 141 23     SPACE eurjchem-32 141 24 1h 1h NUM eurjchem-32 141 25     SPACE eurjchem-32 141 26 nmr nmr NOUN eurjchem-32 141 27     SPACE eurjchem-32 141 28 and and CCONJ eurjchem-32 141 29     SPACE eurjchem-32 141 30 mass mass ADJ eurjchem-32 141 31     SPACE eurjchem-32 141 32 spectrum spectrum NOUN eurjchem-32 141 33 . . PUNCT eurjchem-32 141 34     SPACE eurjchem-32 142 1 the the DET eurjchem-32 142 2     SPACE eurjchem-32 142 3 mass mass NOUN eurjchem-32 142 4     SPACE eurjchem-32 142 5 spectrum spectrum NOUN eurjchem-32 142 6     SPACE eurjchem-32 142 7 showed show VERB eurjchem-32 142 8     SPACE eurjchem-32 142 9 the the DET eurjchem-32 142 10     SPACE eurjchem-32 142 11 molecular molecular ADJ eurjchem-32 142 12     SPACE eurjchem-32 142 13 ion ion NOUN eurjchem-32 142 14     SPACE eurjchem-32 142 15 peak peak NOUN eurjchem-32 142 16     SPACE eurjchem-32 142 17 at at ADP eurjchem-32 142 18     SPACE eurjchem-32 142 19 m m PROPN eurjchem-32 142 20 / / PROPN eurjchem-32 142 21 z z NOUN eurjchem-32 142 22     SPACE eurjchem-32 142 23 371 371 NUM eurjchem-32 142 24     SPACE eurjchem-32 142 25 ( ( PUNCT eurjchem-32 142 26 m+ m+ NUM eurjchem-32 142 27 ) ) PUNCT eurjchem-32 142 28 . . PUNCT eurjchem-32 142 29     SPACE eurjchem-32 143 1 the the DET eurjchem-32 143 2     SPACE eurjchem-32 143 3 1h 1h NUM eurjchem-32 143 4     SPACE eurjchem-32 143 5 nmr nmr NOUN eurjchem-32 143 6     SPACE eurjchem-32 143 7 spectrum spectrum NOUN eurjchem-32 143 8     SPACE eurjchem-32 143 9 of of ADP eurjchem-32 143 10     SPACE eurjchem-32 143 11 this this DET eurjchem-32 143 12     SPACE eurjchem-32 143 13 product product NOUN eurjchem-32 143 14     SPACE eurjchem-32 143 15 did do AUX eurjchem-32 143 16     SPACE eurjchem-32 143 17 not not PART eurjchem-32 143 18     SPACE eurjchem-32 143 19 show show VERB eurjchem-32 143 20     SPACE eurjchem-32 143 21 any any DET eurjchem-32 143 22     SPACE eurjchem-32 143 23 signals signal NOUN eurjchem-32 143 24     SPACE eurjchem-32 143 25 around around ADP eurjchem-32 143 26     SPACE eurjchem-32 143 27 δ δ PROPN eurjchem-32 143 28     SPACE eurjchem-32 143 29 5‐6 5‐6 PRON eurjchem-32 143 30     SPACE eurjchem-32 143 31 ppm ppm ADJ eurjchem-32 143 32     SPACE eurjchem-32 143 33 due due ADJ eurjchem-32 143 34     SPACE eurjchem-32 143 35 to to ADP eurjchem-32 143 36     SPACE eurjchem-32 143 37 a a DET eurjchem-32 143 38     SPACE eurjchem-32 143 39 ch ch NOUN eurjchem-32 143 40     SPACE eurjchem-32 143 41 proton proton NOUN eurjchem-32 143 42     SPACE eurjchem-32 143 43 and and CCONJ eurjchem-32 143 44     SPACE eurjchem-32 143 45 instead instead ADV eurjchem-32 143 46     SPACE eurjchem-32 143 47 reveals reveal VERB eurjchem-32 143 48     SPACE eurjchem-32 143 49 a a DET eurjchem-32 143 50     SPACE eurjchem-32 143 51 singlet singlet NOUN eurjchem-32 143 52     SPACE eurjchem-32 143 53 ( ( PUNCT eurjchem-32 143 54 1h 1h NUM eurjchem-32 143 55 ) ) PUNCT eurjchem-32 143 56     SPACE eurjchem-32 143 57 at at ADP eurjchem-32 143 58     SPACE eurjchem-32 143 59 δ δ PROPN eurjchem-32 143 60     SPACE eurjchem-32 143 61 9.79 9.79 NUM eurjchem-32 143 62     SPACE eurjchem-32 143 63 ppm ppm ADJ eurjchem-32 143 64     SPACE eurjchem-32 143 65 attributable attributable NOUN eurjchem-32 143 66     SPACE eurjchem-32 143 67 to to ADP eurjchem-32 143 68     SPACE eurjchem-32 143 69 the the DET eurjchem-32 143 70     SPACE eurjchem-32 143 71 oh oh NOUN eurjchem-32 143 72     SPACE eurjchem-32 143 73 proton proton NOUN eurjchem-32 143 74     SPACE eurjchem-32 143 75 and and CCONJ eurjchem-32 143 76     SPACE eurjchem-32 143 77 this this PRON eurjchem-32 143 78     SPACE eurjchem-32 143 79 confirms confirm VERB eurjchem-32 143 80     SPACE eurjchem-32 143 81 that that SCONJ eurjchem-32 143 82     SPACE eurjchem-32 143 83 the the DET eurjchem-32 143 84     SPACE eurjchem-32 143 85 most most ADJ eurjchem-32 143 86     SPACE eurjchem-32 143 87 stable stable ADJ eurjchem-32 143 88     SPACE eurjchem-32 143 89 tautomeric tautomeric ADJ eurjchem-32 143 90     SPACE eurjchem-32 143 91 form form NOUN eurjchem-32 143 92     SPACE eurjchem-32 143 93 is be AUX eurjchem-32 143 94     SPACE eurjchem-32 143 95 the the DET eurjchem-32 143 96     SPACE eurjchem-32 143 97 enolic enolic ADJ eurjchem-32 143 98     SPACE eurjchem-32 143 99 form form NOUN eurjchem-32 143 100     SPACE eurjchem-32 143 101 21b 21b NOUN eurjchem-32 143 102 , , PUNCT eurjchem-32 143 103     SPACE eurjchem-32 143 104 as as SCONJ eurjchem-32 143 105     SPACE eurjchem-32 143 106 reported report VERB eurjchem-32 143 107     SPACE eurjchem-32 143 108 for for ADP eurjchem-32 143 109     SPACE eurjchem-32 143 110 β‐diketone β‐diketone NUM eurjchem-32 143 111 . . PUNCT eurjchem-32 143 112     SPACE eurjchem-32 143 113 this this DET eurjchem-32 143 114     SPACE eurjchem-32 143 115 stability stability NOUN eurjchem-32 143 116     SPACE eurjchem-32 143 117 of of ADP eurjchem-32 143 118     SPACE eurjchem-32 143 119 the the DET eurjchem-32 143 120     SPACE eurjchem-32 143 121 enol enol NOUN eurjchem-32 143 122     SPACE eurjchem-32 143 123 form form NOUN eurjchem-32 143 124     SPACE eurjchem-32 143 125 is be AUX eurjchem-32 143 126     SPACE eurjchem-32 143 127 attributed attribute VERB eurjchem-32 143 128     SPACE eurjchem-32 143 129 to to ADP eurjchem-32 143 130     SPACE eurjchem-32 143 131 the the DET eurjchem-32 143 132     SPACE eurjchem-32 143 133 intramolecular intramolecular ADJ eurjchem-32 143 134     SPACE eurjchem-32 143 135 hydrogen hydrogen NOUN eurjchem-32 143 136     SPACE eurjchem-32 143 137 bond bond NOUN eurjchem-32 143 138     SPACE eurjchem-32 143 139 and and CCONJ eurjchem-32 143 140     SPACE eurjchem-32 143 141 also also ADV eurjchem-32 143 142     SPACE eurjchem-32 144 1 due due ADJ eurjchem-32 144 2     SPACE eurjchem-32 144 3 to to ADP eurjchem-32 144 4     SPACE eurjchem-32 144 5 the the DET eurjchem-32 144 6     SPACE eurjchem-32 144 7 conjugation conjugation NOUN eurjchem-32 144 8     SPACE eurjchem-32 144 9 which which PRON eurjchem-32 144 10     SPACE eurjchem-32 144 11 is be AUX eurjchem-32 144 12     SPACE eurjchem-32 144 13 absent absent ADJ eurjchem-32 144 14     SPACE eurjchem-32 144 15 in in ADP eurjchem-32 144 16     SPACE eurjchem-32 144 17 case case NOUN eurjchem-32 144 18     SPACE eurjchem-32 144 19 of of ADP eurjchem-32 144 20     SPACE eurjchem-32 144 21 the the DET eurjchem-32 144 22     SPACE eurjchem-32 144 23 keto keto NOUN eurjchem-32 144 24     SPACE eurjchem-32 144 25 form form NOUN eurjchem-32 144 26 . . PUNCT eurjchem-32 144 27     SPACE eurjchem-32 144 28 this this DET eurjchem-32 144 29     SPACE eurjchem-32 144 30 conjugation conjugation NOUN eurjchem-32 144 31     SPACE eurjchem-32 144 32 is be AUX eurjchem-32 144 33     SPACE eurjchem-32 144 34 also also ADV eurjchem-32 144 35     SPACE eurjchem-32 144 36 reflected reflect VERB eurjchem-32 144 37     SPACE eurjchem-32 144 38 on on ADP eurjchem-32 144 39     SPACE eurjchem-32 144 40 the the DET eurjchem-32 144 41     SPACE eurjchem-32 144 42 color color NOUN eurjchem-32 144 43     SPACE eurjchem-32 144 44 of of ADP eurjchem-32 144 45     SPACE eurjchem-32 144 46 the the DET eurjchem-32 144 47     SPACE eurjchem-32 144 48 product product NOUN eurjchem-32 144 49     SPACE eurjchem-32 144 50 ( ( PUNCT eurjchem-32 144 51 yellow yellow ADJ eurjchem-32 144 52 ) ) PUNCT eurjchem-32 144 53 . . PUNCT eurjchem-32 144 54     SPACE eurjchem-32 145 1 the the DET eurjchem-32 145 2     SPACE eurjchem-32 145 3 1h 1h NUM eurjchem-32 145 4     SPACE eurjchem-32 145 5 nmr nmr NOUN eurjchem-32 145 6     SPACE eurjchem-32 145 7 spectrum spectrum NOUN eurjchem-32 145 8     SPACE eurjchem-32 145 9 showed show VERB eurjchem-32 145 10     SPACE eurjchem-32 145 11 also also ADV eurjchem-32 145 12     SPACE eurjchem-32 145 13 the the DET eurjchem-32 145 14     SPACE eurjchem-32 145 15 presence presence NOUN eurjchem-32 145 16     SPACE eurjchem-32 145 17 of of ADP eurjchem-32 145 18     SPACE eurjchem-32 145 19 multiplet multiplet NOUN eurjchem-32 145 20     SPACE eurjchem-32 145 21 signals signal NOUN eurjchem-32 145 22     SPACE eurjchem-32 145 23 at at ADP eurjchem-32 145 24     SPACE eurjchem-32 145 25 δ δ PROPN eurjchem-32 145 26     SPACE eurjchem-32 145 27 7.41‐8.09 7.41‐8.09 NUM eurjchem-32 145 28     SPACE eurjchem-32 145 29 ppm ppm NOUN eurjchem-32 145 30     SPACE eurjchem-32 145 31 due due ADJ eurjchem-32 145 32     SPACE eurjchem-32 145 33 to to ADP eurjchem-32 145 34     SPACE eurjchem-32 145 35 eleven eleven NUM eurjchem-32 145 36     SPACE eurjchem-32 145 37 aromatic aromatic ADJ eurjchem-32 145 38     SPACE eurjchem-32 145 39 protons proton NOUN eurjchem-32 145 40     SPACE eurjchem-32 145 41 and and CCONJ eurjchem-32 145 42     SPACE eurjchem-32 145 43 one one NUM eurjchem-32 145 44     SPACE eurjchem-32 145 45 singlet singlet NOUN eurjchem-32 145 46     SPACE eurjchem-32 145 47 signal signal NOUN eurjchem-32 145 48     SPACE eurjchem-32 145 49 at at ADP eurjchem-32 145 50     SPACE eurjchem-32 145 51 δ δ PROPN eurjchem-32 145 52     SPACE eurjchem-32 145 53 8.20 8.20 NUM eurjchem-32 145 54     SPACE eurjchem-32 145 55 ppm ppm NOUN eurjchem-32 145 56     SPACE eurjchem-32 145 57 for for ADP eurjchem-32 145 58     SPACE eurjchem-32 145 59 the the DET eurjchem-32 145 60     SPACE eurjchem-32 145 61 nh nh NOUN eurjchem-32 145 62     SPACE eurjchem-32 145 63 proton proton NOUN eurjchem-32 145 64 . . PUNCT eurjchem-32 145 65     SPACE eurjchem-32 146 1 the the DET eurjchem-32 146 2     SPACE eurjchem-32 146 3 ir ir NOUN eurjchem-32 146 4     SPACE eurjchem-32 146 5 spectrum spectrum NOUN eurjchem-32 146 6     SPACE eurjchem-32 146 7 of of ADP eurjchem-32 146 8     SPACE eurjchem-32 146 9 this this DET eurjchem-32 146 10     SPACE eurjchem-32 146 11 product product NOUN eurjchem-32 146 12     SPACE eurjchem-32 146 13 also also ADV eurjchem-32 146 14     SPACE eurjchem-32 146 15 confirmed confirm VERB eurjchem-32 146 16     SPACE eurjchem-32 146 17 the the DET eurjchem-32 146 18     SPACE eurjchem-32 146 19 enol enol NOUN eurjchem-32 146 20     SPACE eurjchem-32 146 21 form form NOUN eurjchem-32 146 22     SPACE eurjchem-32 146 23 since since SCONJ eurjchem-32 146 24     SPACE eurjchem-32 146 25 it it PRON eurjchem-32 146 26     SPACE eurjchem-32 146 27 showed show VERB eurjchem-32 146 28     SPACE eurjchem-32 146 29 absorption absorption NOUN eurjchem-32 146 30     SPACE eurjchem-32 146 31 bands band NOUN eurjchem-32 146 32     SPACE eurjchem-32 146 33 at at ADP eurjchem-32 146 34     SPACE eurjchem-32 146 35 ύ ύ PRON eurjchem-32 146 36     SPACE eurjchem-32 146 37 3441 3441 NUM eurjchem-32 146 38     SPACE eurjchem-32 146 39 ( ( PUNCT eurjchem-32 146 40 oh oh INTJ eurjchem-32 146 41 ) ) PUNCT eurjchem-32 146 42 , , PUNCT eurjchem-32 146 43     SPACE eurjchem-32 146 44 3134 3134 NUM eurjchem-32 146 45     SPACE eurjchem-32 146 46 ( ( PUNCT eurjchem-32 146 47 nh nh NOUN eurjchem-32 146 48 ) ) PUNCT eurjchem-32 146 49 , , PUNCT eurjchem-32 146 50     SPACE eurjchem-32 146 51 2211 2211 NUM eurjchem-32 146 52     SPACE eurjchem-32 146 53 ( ( PUNCT eurjchem-32 146 54 cn cn PROPN eurjchem-32 146 55 ) ) PUNCT eurjchem-32 146 56 , , PUNCT eurjchem-32 146 57     SPACE eurjchem-32 146 58 and and CCONJ eurjchem-32 146 59     SPACE eurjchem-32 146 60 only only ADV eurjchem-32 146 61     SPACE eurjchem-32 146 62 one one NUM eurjchem-32 146 63     SPACE eurjchem-32 146 64 amide amide NOUN eurjchem-32 146 65     SPACE eurjchem-32 146 66 ( ( PUNCT eurjchem-32 146 67 c c NOUN eurjchem-32 146 68 = = NOUN eurjchem-32 146 69 o o NOUN eurjchem-32 146 70 ) ) PUNCT eurjchem-32 146 71     SPACE eurjchem-32 146 72 peak peak NOUN eurjchem-32 146 73     SPACE eurjchem-32 146 74 at at ADP eurjchem-32 146 75     SPACE eurjchem-32 146 76 1631 1631 NUM eurjchem-32 146 77     SPACE eurjchem-32 146 78 cm‐1 cm‐1 NOUN eurjchem-32 146 79 . . PUNCT eurjchem-32 146 80       SPACE eurjchem-32 147 1 the the DET eurjchem-32 147 2     SPACE eurjchem-32 147 3 fused fuse VERB eurjchem-32 147 4     SPACE eurjchem-32 147 5 pyridine pyridine NOUN eurjchem-32 147 6     SPACE eurjchem-32 147 7 ring ring NOUN eurjchem-32 147 8     SPACE eurjchem-32 147 9 2‐(5‐amino‐1,3‐dimethyl‐2,4‐ 2‐(5‐amino‐1,3‐dimethyl‐2,4‐ PROPN eurjchem-32 147 10 dioxo‐1,2,3,4‐tetrahydropyrido[2,3‐d]pyrimidin‐7‐yl)‐2‐(benzo dioxo‐1,2,3,4‐tetrahydropyrido[2,3‐d]pyrimidin‐7‐yl)‐2‐(benzo PROPN eurjchem-32 147 11     SPACE eurjchem-32 147 12 [ [ X eurjchem-32 147 13 d]thiazol‐2‐yl)acetonitrile d]thiazol‐2‐yl)acetonitrile VERB eurjchem-32 147 14     SPACE eurjchem-32 147 15 23 23 NUM eurjchem-32 147 16     SPACE eurjchem-32 147 17 was be AUX eurjchem-32 147 18     SPACE eurjchem-32 147 19 synthesized synthesize VERB eurjchem-32 147 20     SPACE eurjchem-32 147 21 from from ADP eurjchem-32 147 22     SPACE eurjchem-32 147 23 4 4 NUM eurjchem-32 147 24     SPACE eurjchem-32 147 25 by by ADP eurjchem-32 147 26     SPACE eurjchem-32 147 27 reaction reaction NOUN eurjchem-32 147 28     SPACE eurjchem-32 147 29 with with ADP eurjchem-32 147 30     SPACE eurjchem-32 147 31 6‐amino‐1,3‐dimethylpyrimidine‐2,4(1h,3h)‐ 6‐amino‐1,3‐dimethylpyrimidine‐2,4(1h,3h)‐ NUM eurjchem-32 147 32 dione dione NOUN eurjchem-32 147 33     SPACE eurjchem-32 147 34 13 13 NUM eurjchem-32 147 35     SPACE eurjchem-32 147 36 in in ADP eurjchem-32 147 37     SPACE eurjchem-32 147 38 refluxing refluxing NOUN eurjchem-32 147 39     SPACE eurjchem-32 147 40 glacial glacial ADJ eurjchem-32 147 41     SPACE eurjchem-32 147 42 acetic acetic ADJ eurjchem-32 147 43     SPACE eurjchem-32 147 44 acid acid NOUN eurjchem-32 147 45     SPACE eurjchem-32 147 46 containing contain VERB eurjchem-32 147 47     SPACE eurjchem-32 147 48 catalytic catalytic ADJ eurjchem-32 147 49     SPACE eurjchem-32 147 50 amounts amount NOUN eurjchem-32 147 51     SPACE eurjchem-32 147 52 of of ADP eurjchem-32 147 53     SPACE eurjchem-32 147 54 freshly freshly ADV eurjchem-32 147 55     SPACE eurjchem-32 147 56 fused fuse VERB eurjchem-32 147 57     SPACE eurjchem-32 147 58 sodium sodium NOUN eurjchem-32 147 59     SPACE eurjchem-32 147 60 acetate acetate NOUN eurjchem-32 147 61     SPACE eurjchem-32 147 62 presumably presumably ADV eurjchem-32 147 63     SPACE eurjchem-32 147 64 via via ADP eurjchem-32 147 65     SPACE eurjchem-32 147 66 the the DET eurjchem-32 147 67     SPACE eurjchem-32 147 68 intermediates intermediate NOUN eurjchem-32 147 69     SPACE eurjchem-32 147 70 22a 22a NOUN eurjchem-32 147 71     SPACE eurjchem-32 147 72 and and CCONJ eurjchem-32 147 73     SPACE eurjchem-32 147 74 22b 22b NOUN eurjchem-32 147 75     SPACE eurjchem-32 147 76 ( ( PUNCT eurjchem-32 147 77 scheme scheme NOUN eurjchem-32 147 78     SPACE eurjchem-32 147 79 12 12 NUM eurjchem-32 147 80 ) ) PUNCT eurjchem-32 147 81 . . PUNCT eurjchem-32 147 82     SPACE eurjchem-32 148 1 structure structure NOUN eurjchem-32 148 2     SPACE eurjchem-32 148 3 23 23 NUM eurjchem-32 148 4     SPACE eurjchem-32 148 5 was be AUX eurjchem-32 148 6     SPACE eurjchem-32 148 7 proved prove VERB eurjchem-32 148 8     SPACE eurjchem-32 148 9 by by ADP eurjchem-32 148 10     SPACE eurjchem-32 148 11 its its PRON eurjchem-32 148 12     SPACE eurjchem-32 148 13 ir ir NOUN eurjchem-32 148 14     SPACE eurjchem-32 148 15 spectrum spectrum NOUN eurjchem-32 148 16     SPACE eurjchem-32 148 17 which which PRON eurjchem-32 148 18     SPACE eurjchem-32 148 19 revealed reveal VERB eurjchem-32 148 20     SPACE eurjchem-32 148 21 stretching stretch VERB eurjchem-32 148 22     SPACE eurjchem-32 148 23 frequencies frequency NOUN eurjchem-32 148 24     SPACE eurjchem-32 148 25 of of ADP eurjchem-32 148 26     SPACE eurjchem-32 148 27 cn cn NOUN eurjchem-32 148 28     SPACE eurjchem-32 148 29 at at ADP eurjchem-32 148 30     SPACE eurjchem-32 148 31 2216 2216 NUM eurjchem-32 148 32     SPACE eurjchem-32 148 33 cm‐1 cm‐1 NOUN eurjchem-32 148 34 , , PUNCT eurjchem-32 148 35     SPACE eurjchem-32 148 36 nh2 nh2 PROPN eurjchem-32 148 37     SPACE eurjchem-32 148 38 at at ADP eurjchem-32 148 39     SPACE eurjchem-32 148 40 3418 3418 NUM eurjchem-32 148 41 , , PUNCT eurjchem-32 148 42     SPACE eurjchem-32 148 43 3581 3581 NUM eurjchem-32 148 44     SPACE eurjchem-32 148 45 cm‐1 cm‐1 NOUN eurjchem-32 148 46 . . PUNCT eurjchem-32 148 47     SPACE eurjchem-32 149 1 the the DET eurjchem-32 149 2     SPACE eurjchem-32 149 3 1h 1h NUM eurjchem-32 149 4     SPACE eurjchem-32 149 5 nmr nmr NOUN eurjchem-32 149 6     SPACE eurjchem-32 149 7 ( ( PUNCT eurjchem-32 149 8 dmso‐d6 dmso‐d6 NOUN eurjchem-32 149 9 ) ) PUNCT eurjchem-32 149 10     SPACE eurjchem-32 149 11 for for ADP eurjchem-32 149 12     SPACE eurjchem-32 149 13 compound compound NOUN eurjchem-32 149 14     SPACE eurjchem-32 149 15 23 23 NUM eurjchem-32 149 16     SPACE eurjchem-32 149 17 showed show VERB eurjchem-32 149 18     SPACE eurjchem-32 149 19 multiplet multiplet NOUN eurjchem-32 149 20     SPACE eurjchem-32 149 21 bands band NOUN eurjchem-32 149 22     SPACE eurjchem-32 149 23 at at ADP eurjchem-32 149 24     SPACE eurjchem-32 149 25 δ δ PROPN eurjchem-32 149 26     SPACE eurjchem-32 149 27 7.30–8.10 7.30–8.10 ADJ eurjchem-32 149 28     SPACE eurjchem-32 149 29 ppm ppm NOUN eurjchem-32 149 30     SPACE eurjchem-32 149 31 due due ADJ eurjchem-32 149 32     SPACE eurjchem-32 149 33 to to ADP eurjchem-32 149 34     SPACE eurjchem-32 149 35 four four NUM eurjchem-32 149 36     SPACE eurjchem-32 149 37 aromatic aromatic ADJ eurjchem-32 149 38     SPACE eurjchem-32 149 39 protons proton NOUN eurjchem-32 149 40 , , PUNCT eurjchem-32 149 41     SPACE eurjchem-32 149 42 and and CCONJ eurjchem-32 149 43     SPACE eurjchem-32 149 44 broad broad ADJ eurjchem-32 149 45     SPACE eurjchem-32 149 46 band band NOUN eurjchem-32 149 47     SPACE eurjchem-32 149 48 at at ADP eurjchem-32 149 49     SPACE eurjchem-32 149 50 δ δ PROPN eurjchem-32 149 51     SPACE eurjchem-32 149 52 6.22 6.22 NUM eurjchem-32 149 53     SPACE eurjchem-32 149 54 ppm ppm NOUN eurjchem-32 149 55     SPACE eurjchem-32 149 56 due due ADJ eurjchem-32 149 57     SPACE eurjchem-32 149 58 to to PART eurjchem-32 149 59     SPACE eurjchem-32 149 60 nh2 nh2 PROPN eurjchem-32 149 61 , , PUNCT eurjchem-32 149 62     SPACE eurjchem-32 149 63 singlet singlet NOUN eurjchem-32 149 64     SPACE eurjchem-32 149 65 at at ADP eurjchem-32 149 66     SPACE eurjchem-32 149 67 δ δ PROPN eurjchem-32 149 68     SPACE eurjchem-32 149 69 5.9 5.9 NUM eurjchem-32 149 70     SPACE eurjchem-32 149 71 ppm ppm NOUN eurjchem-32 149 72     SPACE eurjchem-32 149 73 due due ADJ eurjchem-32 149 74     SPACE eurjchem-32 149 75 to to PART eurjchem-32 149 76     SPACE eurjchem-32 149 77 c3‐h c3‐h VERB eurjchem-32 149 78     SPACE eurjchem-32 149 79 in in ADP eurjchem-32 149 80     SPACE eurjchem-32 149 81 pyridine pyridine NOUN eurjchem-32 149 82     SPACE eurjchem-32 149 83 ring ring NOUN eurjchem-32 149 84 , , PUNCT eurjchem-32 149 85     SPACE eurjchem-32 149 86 singlet singlet NOUN eurjchem-32 149 87     SPACE eurjchem-32 149 88 signal signal NOUN eurjchem-32 149 89     SPACE eurjchem-32 149 90 at at ADP eurjchem-32 149 91     SPACE eurjchem-32 149 92 δ δ PROPN eurjchem-32 149 93     SPACE eurjchem-32 149 94 4.89 4.89 NUM eurjchem-32 149 95     SPACE eurjchem-32 149 96 ppm ppm NOUN eurjchem-32 149 97     SPACE eurjchem-32 149 98 due due ADJ eurjchem-32 149 99     SPACE eurjchem-32 149 100 to to ADP eurjchem-32 149 101     SPACE eurjchem-32 149 102 ch ch NOUN eurjchem-32 149 103     SPACE eurjchem-32 149 104 proton proton NOUN eurjchem-32 149 105     SPACE eurjchem-32 149 106 and and CCONJ eurjchem-32 149 107     SPACE eurjchem-32 149 108 two two NUM eurjchem-32 149 109     SPACE eurjchem-32 149 110 singlet singlet NOUN eurjchem-32 149 111     SPACE eurjchem-32 149 112 signal signal NOUN eurjchem-32 149 113     SPACE eurjchem-32 149 114 at at ADP eurjchem-32 149 115     SPACE eurjchem-32 149 116 δ δ PROPN eurjchem-32 149 117     SPACE eurjchem-32 149 118 3.25 3.25 NUM eurjchem-32 149 119 , , PUNCT eurjchem-32 149 120     SPACE eurjchem-32 149 121 3.37 3.37 NUM eurjchem-32 149 122     SPACE eurjchem-32 149 123 ppm ppm NOUN eurjchem-32 149 124     SPACE eurjchem-32 149 125 due due ADJ eurjchem-32 149 126     SPACE eurjchem-32 149 127 to to ADP eurjchem-32 149 128     SPACE eurjchem-32 149 129 two two NUM eurjchem-32 149 130     SPACE eurjchem-32 149 131 ch3 ch3 PROPN eurjchem-32 149 132     SPACE eurjchem-32 149 133 groups group NOUN eurjchem-32 149 134 . . PUNCT eurjchem-32 149 135     SPACE eurjchem-32 150 1 the the DET eurjchem-32 150 2     SPACE eurjchem-32 150 3 mass mass NOUN eurjchem-32 150 4     SPACE eurjchem-32 150 5 spectrum spectrum NOUN eurjchem-32 150 6     SPACE eurjchem-32 150 7 of of ADP eurjchem-32 150 8     SPACE eurjchem-32 150 9 23 23 NUM eurjchem-32 150 10     SPACE eurjchem-32 150 11 showed show VERB eurjchem-32 150 12     SPACE eurjchem-32 150 13 the the DET eurjchem-32 150 14     SPACE eurjchem-32 150 15 molecular molecular ADJ eurjchem-32 150 16     SPACE eurjchem-32 150 17 ion ion NOUN eurjchem-32 150 18     SPACE eurjchem-32 150 19 peak peak NOUN eurjchem-32 150 20     SPACE eurjchem-32 150 21 at at ADP eurjchem-32 150 22     SPACE eurjchem-32 150 23 m m PROPN eurjchem-32 150 24 / / PROPN eurjchem-32 150 25 z z NOUN eurjchem-32 150 26     SPACE eurjchem-32 150 27 348 348 NUM eurjchem-32 150 28     SPACE eurjchem-32 150 29 ( ( PUNCT eurjchem-32 150 30 m+‐30 m+‐30 PROPN eurjchem-32 150 31 ) ) PUNCT eurjchem-32 150 32     SPACE eurjchem-32 150 33 which which PRON eurjchem-32 150 34     SPACE eurjchem-32 150 35 represents represent VERB eurjchem-32 150 36     SPACE eurjchem-32 150 37 ( ( PUNCT eurjchem-32 150 38 m+ m+ NOUN eurjchem-32 150 39     SPACE eurjchem-32 150 40 ‐2ch3 ‐2ch3 NOUN eurjchem-32 150 41 ) ) PUNCT eurjchem-32 150 42 . . PUNCT eurjchem-32 150 43     SPACE eurjchem-32 151 1 the the DET eurjchem-32 151 2     SPACE eurjchem-32 151 3 thiophene thiophene NOUN eurjchem-32 151 4     SPACE eurjchem-32 151 5 heterocyclic heterocyclic NOUN eurjchem-32 151 6     SPACE eurjchem-32 151 7 ring ring NOUN eurjchem-32 151 8     SPACE eurjchem-32 151 9 incorporating incorporate VERB eurjchem-32 151 10     SPACE eurjchem-32 151 11 a a DET eurjchem-32 151 12     SPACE eurjchem-32 151 13 benzothiazole benzothiazole NOUN eurjchem-32 151 14     SPACE eurjchem-32 151 15 moiety moiety NOUN eurjchem-32 151 16     SPACE eurjchem-32 151 17 was be AUX eurjchem-32 151 18     SPACE eurjchem-32 151 19 prepared prepare VERB eurjchem-32 151 20     SPACE eurjchem-32 151 21 directly directly ADV eurjchem-32 151 22     SPACE eurjchem-32 151 23 from from ADP eurjchem-32 151 24     SPACE eurjchem-32 151 25 compound compound NOUN eurjchem-32 151 26     SPACE eurjchem-32 151 27 4 4 NUM eurjchem-32 151 28 . . PUNCT eurjchem-32 151 29     SPACE eurjchem-32 151 30 thus thus ADV eurjchem-32 151 31     SPACE eurjchem-32 151 32 treatment treatment NOUN eurjchem-32 151 33     SPACE eurjchem-32 151 34 of of ADP eurjchem-32 151 35     SPACE eurjchem-32 151 36 4 4 NUM eurjchem-32 151 37     SPACE eurjchem-32 151 38 with with ADP eurjchem-32 151 39     SPACE eurjchem-32 151 40 sulfur sulfur NOUN eurjchem-32 151 41     SPACE eurjchem-32 151 42 element element NOUN eurjchem-32 151 43     SPACE eurjchem-32 151 44 in in ADP eurjchem-32 151 45     SPACE eurjchem-32 151 46 the the DET eurjchem-32 151 47     SPACE eurjchem-32 151 48 presence presence NOUN eurjchem-32 151 49     SPACE eurjchem-32 151 50 of of ADP eurjchem-32 151 51     SPACE eurjchem-32 151 52 tea tea NOUN eurjchem-32 151 53     SPACE eurjchem-32 151 54 ( ( PUNCT eurjchem-32 151 55 slightly slightly ADV eurjchem-32 151 56     SPACE eurjchem-32 151 57 excess excess NOUN eurjchem-32 151 58 ) ) PUNCT eurjchem-32 151 59     SPACE eurjchem-32 151 60 afforded afford VERB eurjchem-32 151 61     SPACE eurjchem-32 151 62 the the DET eurjchem-32 151 63     SPACE eurjchem-32 151 64 corresponding corresponding ADJ eurjchem-32 151 65     SPACE eurjchem-32 151 66 thiophene thiophene NOUN eurjchem-32 151 67     SPACE eurjchem-32 151 68 24 24 NUM eurjchem-32 151 69 , , PUNCT eurjchem-32 151 70     SPACE eurjchem-32 151 71 while while SCONJ eurjchem-32 151 72     SPACE eurjchem-32 151 73 when when SCONJ eurjchem-32 151 74     SPACE eurjchem-32 151 75 the the DET eurjchem-32 151 76     SPACE eurjchem-32 151 77 reaction reaction NOUN eurjchem-32 151 78     SPACE eurjchem-32 151 79 was be AUX eurjchem-32 151 80     SPACE eurjchem-32 151 81 carried carry VERB eurjchem-32 151 82     SPACE eurjchem-32 151 83 out out ADP eurjchem-32 151 84     SPACE eurjchem-32 151 85 in in ADP eurjchem-32 151 86     SPACE eurjchem-32 151 87 the the DET eurjchem-32 151 88     SPACE eurjchem-32 151 89 presence presence NOUN eurjchem-32 151 90     SPACE eurjchem-32 151 91 of of ADP eurjchem-32 151 92     SPACE eurjchem-32 151 93 morpholine morpholine NOUN eurjchem-32 151 94 , , PUNCT eurjchem-32 151 95     SPACE eurjchem-32 151 96 it it PRON eurjchem-32 151 97     SPACE eurjchem-32 151 98 afforded afford VERB eurjchem-32 151 99     SPACE eurjchem-32 151 100 the the DET eurjchem-32 151 101     SPACE eurjchem-32 151 102 tetrahydrothienopyridine tetrahydrothienopyridine NOUN eurjchem-32 151 103     SPACE eurjchem-32 151 104 25 25 NUM eurjchem-32 151 105     SPACE eurjchem-32 151 106 ( ( PUNCT eurjchem-32 151 107 scheme scheme NOUN eurjchem-32 151 108     SPACE eurjchem-32 151 109 13,14 13,14 NUM eurjchem-32 151 110 ) ) PUNCT eurjchem-32 151 111 . . PUNCT eurjchem-32 151 112         SPACE eurjchem-32 152 1 scheme scheme NOUN eurjchem-32 152 2     SPACE eurjchem-32 152 3 14 14 NUM eurjchem-32 152 4         SPACE eurjchem-32 152 5 the the DET eurjchem-32 152 6     SPACE eurjchem-32 152 7 formation formation NOUN eurjchem-32 152 8     SPACE eurjchem-32 152 9 of of ADP eurjchem-32 152 10     SPACE eurjchem-32 152 11 5‐amino‐4‐(benzo[d]thiazol‐2‐yl)‐3‐ 5‐amino‐4‐(benzo[d]thiazol‐2‐yl)‐3‐ NUM eurjchem-32 152 12 hydroxy‐thiophene‐2‐carbonitrile hydroxy‐thiophene‐2‐carbonitrile NOUN eurjchem-32 152 13     SPACE eurjchem-32 152 14 24 24 NUM eurjchem-32 152 15     SPACE eurjchem-32 152 16 was be AUX eurjchem-32 152 17     SPACE eurjchem-32 152 18 established establish VERB eurjchem-32 152 19     SPACE eurjchem-32 152 20 by by ADP eurjchem-32 152 21     SPACE eurjchem-32 152 22 its its PRON eurjchem-32 152 23     SPACE eurjchem-32 152 24 ir ir PROPN eurjchem-32 152 25 , , PUNCT eurjchem-32 152 26     SPACE eurjchem-32 152 27 mass mass PROPN eurjchem-32 152 28     SPACE eurjchem-32 152 29 spectrum spectrum NOUN eurjchem-32 152 30     SPACE eurjchem-32 152 31 and and CCONJ eurjchem-32 152 32     SPACE eurjchem-32 152 33 1h 1h NUM eurjchem-32 152 34     SPACE eurjchem-32 152 35 nmr nmr NOUN eurjchem-32 152 36 . . PUNCT eurjchem-32 152 37     SPACE eurjchem-32 153 1 the the DET eurjchem-32 153 2     SPACE eurjchem-32 153 3 ir ir NOUN eurjchem-32 153 4     SPACE eurjchem-32 153 5 spectrum spectrum NOUN eurjchem-32 153 6     SPACE eurjchem-32 153 7 of of ADP eurjchem-32 153 8     SPACE eurjchem-32 153 9 24 24 NUM eurjchem-32 153 10     SPACE eurjchem-32 153 11 showed show VERB eurjchem-32 153 12     SPACE eurjchem-32 153 13 broad broad ADJ eurjchem-32 153 14     SPACE eurjchem-32 153 15 band band NOUN eurjchem-32 153 16     SPACE eurjchem-32 153 17 at at ADP eurjchem-32 153 18     SPACE eurjchem-32 153 19 3454 3454 NUM eurjchem-32 153 20     SPACE eurjchem-32 153 21 cm‐1 cm‐1 NOUN eurjchem-32 153 22     SPACE eurjchem-32 153 23 due due ADJ eurjchem-32 153 24     SPACE eurjchem-32 153 25 to to PART eurjchem-32 153 26     SPACE eurjchem-32 153 27 oh oh INTJ eurjchem-32 153 28 , , PUNCT eurjchem-32 153 29     SPACE eurjchem-32 153 30 3396 3396 NUM eurjchem-32 153 31 , , PUNCT eurjchem-32 153 32     SPACE eurjchem-32 153 33 3345 3345 NUM eurjchem-32 153 34     SPACE eurjchem-32 153 35 cm‐1 cm‐1 NOUN eurjchem-32 153 36     SPACE eurjchem-32 153 37 ( ( PUNCT eurjchem-32 153 38 nh2 nh2 PROPN eurjchem-32 153 39 ) ) PUNCT eurjchem-32 153 40 . . PUNCT eurjchem-32 153 41     SPACE eurjchem-32 154 1 the the DET eurjchem-32 154 2     SPACE eurjchem-32 154 3 1h 1h NUM eurjchem-32 154 4     SPACE eurjchem-32 154 5 nmr nmr NOUN eurjchem-32 154 6     SPACE eurjchem-32 154 7 spectrum spectrum NOUN eurjchem-32 154 8     SPACE eurjchem-32 154 9 showed show VERB eurjchem-32 154 10     SPACE eurjchem-32 154 11 two two NUM eurjchem-32 154 12     SPACE eurjchem-32 154 13 broad broad ADJ eurjchem-32 154 14     SPACE eurjchem-32 154 15 singlet singlet NOUN eurjchem-32 154 16     SPACE eurjchem-32 154 17 signals signal NOUN eurjchem-32 154 18     SPACE eurjchem-32 154 19 at at ADP eurjchem-32 154 20     SPACE eurjchem-32 154 21 δ δ PROPN eurjchem-32 154 22     SPACE eurjchem-32 154 23 6.12 6.12 NUM eurjchem-32 154 24     SPACE eurjchem-32 154 25 and and CCONJ eurjchem-32 154 26     SPACE eurjchem-32 154 27 6.67 6.67 NUM eurjchem-32 154 28     SPACE eurjchem-32 154 29 ppm ppm NOUN eurjchem-32 154 30     SPACE eurjchem-32 154 31 due due ADJ eurjchem-32 154 32     SPACE eurjchem-32 154 33 to to ADP eurjchem-32 154 34     SPACE eurjchem-32 154 35 oh oh NOUN eurjchem-32 154 36     SPACE eurjchem-32 154 37 and and CCONJ eurjchem-32 154 38     SPACE eurjchem-32 154 39 nh2 nh2 NOUN eurjchem-32 154 40     SPACE eurjchem-32 154 41 protons proton NOUN eurjchem-32 154 42     SPACE eurjchem-32 154 43 respectively respectively ADV eurjchem-32 154 44 , , PUNCT eurjchem-32 154 45     SPACE eurjchem-32 154 46 in in ADP eurjchem-32 154 47     SPACE eurjchem-32 154 48 addition addition NOUN eurjchem-32 154 49     SPACE eurjchem-32 154 50 to to ADP eurjchem-32 154 51     SPACE eurjchem-32 154 52 multiplet multiplet NOUN eurjchem-32 154 53     SPACE eurjchem-32 154 54 signal signal NOUN eurjchem-32 154 55     SPACE eurjchem-32 154 56 at at ADP eurjchem-32 154 57     SPACE eurjchem-32 154 58 δ δ PROPN eurjchem-32 154 59     SPACE eurjchem-32 154 60 7.21‐8.32 7.21‐8.32 NUM eurjchem-32 154 61     SPACE eurjchem-32 154 62 ppm ppm NOUN eurjchem-32 154 63     SPACE eurjchem-32 154 64 due due ADJ eurjchem-32 154 65     SPACE eurjchem-32 154 66 to to ADP eurjchem-32 154 67     SPACE eurjchem-32 154 68 four four NUM eurjchem-32 154 69     SPACE eurjchem-32 154 70 aromatic aromatic ADJ eurjchem-32 154 71     SPACE eurjchem-32 154 72 protons proton NOUN eurjchem-32 154 73 . . PUNCT eurjchem-32 154 74     SPACE eurjchem-32 154 75 the the DET eurjchem-32 154 76     SPACE eurjchem-32 154 77 mass mass ADJ eurjchem-32 154 78     SPACE eurjchem-32 154 79 spectrum spectrum NOUN eurjchem-32 154 80     SPACE eurjchem-32 154 81 showed show VERB eurjchem-32 154 82     SPACE eurjchem-32 154 83 the the DET eurjchem-32 154 84     SPACE eurjchem-32 154 85 molecular molecular ADJ eurjchem-32 154 86     SPACE eurjchem-32 154 87 ion ion NOUN eurjchem-32 154 88     SPACE eurjchem-32 154 89 peak peak NOUN eurjchem-32 154 90     SPACE eurjchem-32 154 91 at at ADP eurjchem-32 154 92     SPACE eurjchem-32 154 93 m m PROPN eurjchem-32 154 94 / / PROPN eurjchem-32 154 95 z z NOUN eurjchem-32 154 96     SPACE eurjchem-32 154 97 271 271 NUM eurjchem-32 154 98     SPACE eurjchem-32 154 99 ( ( PUNCT eurjchem-32 154 100 m+‐2 m+‐2 NOUN eurjchem-32 154 101 ) ) PUNCT eurjchem-32 154 102 . . PUNCT eurjchem-32 154 103     SPACE eurjchem-32 155 1 the the DET eurjchem-32 155 2     SPACE eurjchem-32 155 3 ir ir NOUN eurjchem-32 155 4     SPACE eurjchem-32 155 5 spectrum spectrum NOUN eurjchem-32 155 6     SPACE eurjchem-32 155 7 of of ADP eurjchem-32 155 8     SPACE eurjchem-32 155 9 25 25 NUM eurjchem-32 155 10     SPACE eurjchem-32 155 11 showed show VERB eurjchem-32 155 12     SPACE eurjchem-32 155 13 stretching stretch VERB eurjchem-32 155 14     SPACE eurjchem-32 155 15 frequencies frequency NOUN eurjchem-32 155 16     SPACE eurjchem-32 155 17 at at ADP eurjchem-32 155 18     SPACE eurjchem-32 155 19 3220 3220 NUM eurjchem-32 155 20     SPACE eurjchem-32 155 21 cm‐1 cm‐1 NOUN eurjchem-32 155 22     SPACE eurjchem-32 155 23 due due ADJ eurjchem-32 155 24     SPACE eurjchem-32 155 25 to to ADP eurjchem-32 155 26     SPACE eurjchem-32 155 27 nh nh PROPN eurjchem-32 155 28     SPACE eurjchem-32 155 29 group group NOUN eurjchem-32 155 30     SPACE eurjchem-32 155 31 and and CCONJ eurjchem-32 155 32     SPACE eurjchem-32 155 33 at at ADP eurjchem-32 155 34     SPACE eurjchem-32 155 35 2195 2195 NUM eurjchem-32 155 36 , , PUNCT eurjchem-32 155 37     SPACE eurjchem-32 155 38 2220 2220 NUM eurjchem-32 155 39     SPACE eurjchem-32 155 40 cm‐1 cm‐1 NOUN eurjchem-32 155 41     SPACE eurjchem-32 155 42 for for ADP eurjchem-32 155 43     SPACE eurjchem-32 155 44 two two NUM eurjchem-32 155 45     SPACE eurjchem-32 155 46 cyano cyano NOUN eurjchem-32 155 47     SPACE eurjchem-32 155 48 functions function NOUN eurjchem-32 155 49 . . PUNCT eurjchem-32 155 50     SPACE eurjchem-32 156 1 the the DET eurjchem-32 156 2     SPACE eurjchem-32 156 3 mass mass NOUN eurjchem-32 156 4     SPACE eurjchem-32 156 5 spectrum spectrum NOUN eurjchem-32 156 6     SPACE eurjchem-32 156 7 showed show VERB eurjchem-32 156 8     SPACE eurjchem-32 156 9 the the DET eurjchem-32 156 10     SPACE eurjchem-32 156 11 molecular molecular ADJ eurjchem-32 156 12     SPACE eurjchem-32 156 13 ion ion NOUN eurjchem-32 156 14     SPACE eurjchem-32 156 15 peak peak NOUN eurjchem-32 156 16     SPACE eurjchem-32 156 17 at at ADP eurjchem-32 156 18     SPACE eurjchem-32 156 19 m m PROPN eurjchem-32 156 20 / / PROPN eurjchem-32 156 21 z z NOUN eurjchem-32 156 22     SPACE eurjchem-32 156 23 470 470 NUM eurjchem-32 156 24     SPACE eurjchem-32 156 25 ( ( PUNCT eurjchem-32 156 26 m+‐1 m+‐1 PROPN eurjchem-32 156 27 ) ) PUNCT eurjchem-32 156 28 . . PUNCT eurjchem-32 156 29     SPACE eurjchem-32 156 30 structure structure NOUN eurjchem-32 156 31     SPACE eurjchem-32 156 32 of of ADP eurjchem-32 156 33     SPACE eurjchem-32 156 34 25 25 NUM eurjchem-32 156 35     SPACE eurjchem-32 156 36 was be AUX eurjchem-32 156 37     SPACE eurjchem-32 156 38 also also ADV eurjchem-32 156 39     SPACE eurjchem-32 156 40 established establish VERB eurjchem-32 156 41     SPACE eurjchem-32 156 42 by by ADP eurjchem-32 156 43     SPACE eurjchem-32 156 44 its its PRON eurjchem-32 156 45     SPACE eurjchem-32 156 46 1h 1h NUM eurjchem-32 156 47     SPACE eurjchem-32 156 48 nmr nmr NOUN eurjchem-32 156 49     SPACE eurjchem-32 156 50 ( ( PUNCT eurjchem-32 156 51 c.f c.f PROPN eurjchem-32 156 52 . . PROPN eurjchem-32 156 53     SPACE eurjchem-32 156 54 experimental experimental ADJ eurjchem-32 156 55 ) ) PUNCT eurjchem-32 156 56 . . PUNCT eurjchem-32 156 57         SPACE eurjchem-32 157 1 acknowledgement acknowledgement NOUN eurjchem-32 157 2                 SPACE eurjchem-32 157 3 we we PRON eurjchem-32 157 4     SPACE eurjchem-32 157 5 thank thank VERB eurjchem-32 157 6     SPACE eurjchem-32 157 7 the the DET eurjchem-32 157 8     SPACE eurjchem-32 157 9 alexander alexander PROPN eurjchem-32 157 10     SPACE eurjchem-32 157 11 von von PROPN eurjchem-32 157 12     SPACE eurjchem-32 157 13 humboldt humboldt PROPN eurjchem-32 157 14     SPACE eurjchem-32 157 15 foundation foundation PROPN eurjchem-32 157 16     SPACE eurjchem-32 157 17 ( ( PUNCT eurjchem-32 157 18 germany germany PROPN eurjchem-32 157 19 ) ) PUNCT eurjchem-32 157 20     SPACE eurjchem-32 157 21 for for ADP eurjchem-32 157 22     SPACE eurjchem-32 157 23 the the DET eurjchem-32 157 24     SPACE eurjchem-32 157 25 continual continual ADJ eurjchem-32 157 26     SPACE eurjchem-32 157 27 support support NOUN eurjchem-32 157 28     SPACE eurjchem-32 157 29 to to ADP eurjchem-32 157 30     SPACE eurjchem-32 157 31 f. f. PROPN eurjchem-32 157 32     SPACE eurjchem-32 157 33 m. m. NOUN eurjchem-32 157 34     SPACE eurjchem-32 157 35 abdelrazek abdelrazek NOUN eurjchem-32 157 36     SPACE eurjchem-32 157 37 by by ADP eurjchem-32 157 38     SPACE eurjchem-32 157 39 granting grant VERB eurjchem-32 157 40     SPACE eurjchem-32 157 41 him he PRON eurjchem-32 157 42     SPACE eurjchem-32 157 43 repeated repeat VERB eurjchem-32 157 44     SPACE eurjchem-32 157 45 research research NOUN eurjchem-32 157 46     SPACE eurjchem-32 157 47 fellowships fellowship NOUN eurjchem-32 157 48 . . PUNCT eurjchem-32 157 49     SPACE eurjchem-32 157 50 this this DET eurjchem-32 157 51     SPACE eurjchem-32 157 52 work work NOUN eurjchem-32 157 53     SPACE eurjchem-32 157 54 was be AUX eurjchem-32 157 55     SPACE eurjchem-32 157 56 supported support VERB eurjchem-32 157 57     SPACE eurjchem-32 157 58 in in ADP eurjchem-32 157 59     SPACE eurjchem-32 157 60 part part NOUN eurjchem-32 157 61     SPACE eurjchem-32 157 62 by by ADP eurjchem-32 157 63     SPACE eurjchem-32 157 64 the the DET eurjchem-32 157 65     SPACE eurjchem-32 157 66 research research NOUN eurjchem-32 157 67     SPACE eurjchem-32 157 68 fund fund NOUN eurjchem-32 157 69     SPACE eurjchem-32 157 70 of of ADP eurjchem-32 157 71     SPACE eurjchem-32 157 72 the the DET eurjchem-32 157 73     SPACE eurjchem-32 157 74 faculty faculty NOUN eurjchem-32 157 75     SPACE eurjchem-32 157 76 of of ADP eurjchem-32 157 77     SPACE eurjchem-32 157 78 science science NOUN eurjchem-32 157 79 , , PUNCT eurjchem-32 157 80     SPACE eurjchem-32 157 81 cairo cairo PROPN eurjchem-32 157 82     SPACE eurjchem-32 157 83 university university PROPN eurjchem-32 157 84 . . PUNCT eurjchem-32 157 85         SPACE eurjchem-32 158 1 references reference NOUN eurjchem-32 158 2           SPACE eurjchem-32 158 3 [ [ X eurjchem-32 158 4 1 1 NUM eurjchem-32 158 5 ] ] PUNCT eurjchem-32 158 6 . . PUNCT eurjchem-32 159 1 hayashi hayashi PROPN eurjchem-32 159 2 , , PUNCT eurjchem-32 159 3     SPACE eurjchem-32 159 4 h. h. PROPN eurjchem-32 159 5 ; ; PUNCT eurjchem-32 159 6     SPACE eurjchem-32 159 7 ohmoto ohmoto NOUN eurjchem-32 159 8 , , PUNCT eurjchem-32 159 9     SPACE eurjchem-32 159 10 s. s. PROPN eurjchem-32 159 11 ; ; PUNCT eurjchem-32 159 12     SPACE eurjchem-32 159 13 somei somei PROPN eurjchem-32 159 14 , , PUNCT eurjchem-32 159 15     SPACE eurjchem-32 159 16 m. m. NOUN eurjchem-32 159 17     SPACE eurjchem-32 159 18 heterocycles heterocycle NOUN eurjchem-32 159 19     SPACE eurjchem-32 159 20 1997 1997 NUM eurjchem-32 159 21 , , PUNCT eurjchem-32 159 22     SPACE eurjchem-32 159 23 45 45 NUM eurjchem-32 159 24 , , PUNCT eurjchem-32 159 25     SPACE eurjchem-32 159 26 1647‐1650 1647‐1650 NUM eurjchem-32 159 27 . . PUNCT eurjchem-32 159 28     SPACE eurjchem-32 160 1 [ [ X eurjchem-32 160 2 2 2 NUM eurjchem-32 160 3 ] ] PUNCT eurjchem-32 160 4 . . PUNCT eurjchem-32 160 5 eby eby PROPN eurjchem-32 160 6 , , PUNCT eurjchem-32 160 7     SPACE eurjchem-32 160 8 c. c. PROPN eurjchem-32 160 9     SPACE eurjchem-32 160 10 j. j. PROPN eurjchem-32 160 11 ; ; PUNCT eurjchem-32 160 12     SPACE eurjchem-32 160 13 hauser hauser PROPN eurjchem-32 160 14 , , PUNCT eurjchem-32 160 15     SPACE eurjchem-32 160 16 c. c. PROPN eurjchem-32 160 17     SPACE eurjchem-32 160 18 r. r. PROPN eurjchem-32 160 19     SPACE eurjchem-32 160 20 j. j. PROPN eurjchem-32 160 21     SPACE eurjchem-32 160 22 am be AUX eurjchem-32 160 23 . . PUNCT eurjchem-32 160 24     SPACE eurjchem-32 160 25 chem chem NOUN eurjchem-32 160 26 . . PUNCT eurjchem-32 160 27     SPACE eurjchem-32 160 28 soc soc PROPN eurjchem-32 160 29 . . PUNCT eurjchem-32 160 30     SPACE eurjchem-32 161 1 1957 1957 NUM eurjchem-32 161 2 , , PUNCT eurjchem-32 161 3     SPACE eurjchem-32 161 4 79 79 NUM eurjchem-32 161 5 , , PUNCT eurjchem-32 161 6     SPACE eurjchem-32 161 7 723‐725 723‐725 NUM eurjchem-32 161 8 . . PUNCT eurjchem-32 161 9     SPACE eurjchem-32 162 1 [ [ X eurjchem-32 162 2 3 3 NUM eurjchem-32 162 3 ] ] PUNCT eurjchem-32 162 4 . . PUNCT eurjchem-32 163 1 schroeter schroeter ADJ eurjchem-32 163 2 , , PUNCT eurjchem-32 163 3     SPACE eurjchem-32 163 4 g. g. NOUN eurjchem-32 163 5 ; ; PUNCT eurjchem-32 163 6     SPACE eurjchem-32 163 7 sildler sildler NOUN eurjchem-32 163 8 , , PUNCT eurjchem-32 163 9     SPACE eurjchem-32 163 10 c. c. NOUN eurjchem-32 163 11 ; ; PUNCT eurjchem-32 163 12     SPACE eurjchem-32 163 13 sulzbacher sulzbacher NOUN eurjchem-32 163 14 , , PUNCT eurjchem-32 163 15     SPACE eurjchem-32 163 16 m. m. NOUN eurjchem-32 163 17 ; ; PUNCT eurjchem-32 163 18     SPACE eurjchem-32 163 19 kanitz kanitz PROPN eurjchem-32 163 20 , , PUNCT eurjchem-32 163 21     SPACE eurjchem-32 163 22 r. r. NOUN eurjchem-32 163 23     SPACE eurjchem-32 163 24 chem chem NOUN eurjchem-32 163 25 . . PUNCT eurjchem-32 163 26     SPACE eurjchem-32 164 1 ber ber PROPN eurjchem-32 164 2 . . PUNCT eurjchem-32 164 3     SPACE eurjchem-32 165 1 1932 1932 NUM eurjchem-32 165 2 , , PUNCT eurjchem-32 165 3     SPACE eurjchem-32 165 4 65 65 NUM eurjchem-32 165 5 , , PUNCT eurjchem-32 165 6     SPACE eurjchem-32 165 7 432‐445 432‐445 NOUN eurjchem-32 165 8 . . PUNCT eurjchem-32 165 9     SPACE eurjchem-32 166 1 [ [ X eurjchem-32 166 2 4 4 NUM eurjchem-32 166 3 ] ] PUNCT eurjchem-32 166 4 . . PUNCT eurjchem-32 166 5 papesch papesch PROPN eurjchem-32 166 6 , , PUNCT eurjchem-32 166 7     SPACE eurjchem-32 166 8 v. v. ADV eurjchem-32 166 9 ; ; PUNCT eurjchem-32 166 10     SPACE eurjchem-32 166 11 schroeder schroeder NOUN eurjchem-32 166 12 , , PUNCT eurjchem-32 166 13     SPACE eurjchem-32 166 14 e. e. PROPN eurjchem-32 166 15     SPACE eurjchem-32 166 16 j. j. PROPN eurjchem-32 166 17     SPACE eurjchem-32 166 18 org org PROPN eurjchem-32 166 19 . . PUNCT eurjchem-32 166 20     SPACE eurjchem-32 166 21 chem chem NOUN eurjchem-32 166 22 . . PUNCT eurjchem-32 166 23     SPACE eurjchem-32 166 24 1951 1951 NUM eurjchem-32 166 25 , , PUNCT eurjchem-32 166 26     SPACE eurjchem-32 166 27 16 16 NUM eurjchem-32 166 28 , , PUNCT eurjchem-32 166 29     SPACE eurjchem-32 166 30 1879‐1890 1879‐1890 NOUN eurjchem-32 166 31 . . PUNCT eurjchem-32 166 32     SPACE eurjchem-32 167 1 [ [ X eurjchem-32 167 2 5 5 NUM eurjchem-32 167 3 ] ] PUNCT eurjchem-32 167 4 . . PUNCT eurjchem-32 167 5 muller muller PROPN eurjchem-32 167 6 , , PUNCT eurjchem-32 167 7     SPACE eurjchem-32 167 8 t. t. PROPN eurjchem-32 167 9 ; ; PUNCT eurjchem-32 167 10     SPACE eurjchem-32 167 11 augustin augustin PROPN eurjchem-32 167 12 , , PUNCT eurjchem-32 167 13     SPACE eurjchem-32 167 14 m. m. NOUN eurjchem-32 167 15 ; ; PUNCT eurjchem-32 167 16     SPACE eurjchem-32 167 17 werchan werchan NOUN eurjchem-32 167 18 , , PUNCT eurjchem-32 167 19     SPACE eurjchem-32 167 20 h. h. PROPN eurjchem-32 167 21     SPACE eurjchem-32 167 22 g. g. PROPN eurjchem-32 167 23     SPACE eurjchem-32 167 24 z. z. PROPN eurjchem-32 167 25     SPACE eurjchem-32 167 26 chem chem NOUN eurjchem-32 167 27 . . PUNCT eurjchem-32 167 28     SPACE eurjchem-32 167 29 1989 1989 NUM eurjchem-32 167 30 , , PUNCT eurjchem-32 167 31     SPACE eurjchem-32 167 32 29 29 NUM eurjchem-32 167 33 , , PUNCT eurjchem-32 167 34     SPACE eurjchem-32 167 35 281‐283 281‐283 NOUN eurjchem-32 167 36 . . PUNCT eurjchem-32 167 37     SPACE eurjchem-32 168 1 [ [ X eurjchem-32 168 2 6 6 NUM eurjchem-32 168 3 ] ] PUNCT eurjchem-32 168 4 . . PUNCT eurjchem-32 169 1 isobe isobe NOUN eurjchem-32 169 2 , , PUNCT eurjchem-32 169 3     SPACE eurjchem-32 169 4 y. y. NOUN eurjchem-32 169 5 ; ; PUNCT eurjchem-32 169 6     SPACE eurjchem-32 169 7 tobe tobe VERB eurjchem-32 169 8 , , PUNCT eurjchem-32 169 9     SPACE eurjchem-32 169 10 m. m. NOUN eurjchem-32 169 11 ; ; PUNCT eurjchem-32 169 12     SPACE eurjchem-32 169 13 inoue inoue NOUN eurjchem-32 169 14 , , PUNCT eurjchem-32 169 15     SPACE eurjchem-32 169 16 y. y. NOUN eurjchem-32 169 17 ; ; PUNCT eurjchem-32 169 18     SPACE eurjchem-32 169 19 hayashi hayashi PROPN eurjchem-32 169 20 , , PUNCT eurjchem-32 169 21     SPACE eurjchem-32 169 22 h. h. NOUN eurjchem-32 169 23     SPACE eurjchem-32 169 24 bioorg bioorg PROPN eurjchem-32 169 25 . . PUNCT eurjchem-32 169 26     SPACE eurjchem-32 169 27 & & CCONJ eurjchem-32 169 28     SPACE eurjchem-32 169 29 med med PROPN eurjchem-32 169 30 . . PUNCT eurjchem-32 169 31     SPACE eurjchem-32 169 32 chem chem NOUN eurjchem-32 169 33 . . PUNCT eurjchem-32 169 34     SPACE eurjchem-32 169 35 2003 2003 NUM eurjchem-32 169 36 , , PUNCT eurjchem-32 169 37     SPACE eurjchem-32 169 38 11 11 NUM eurjchem-32 169 39 , , PUNCT eurjchem-32 169 40     SPACE eurjchem-32 169 41 4933‐4940 4933‐4940 NUM eurjchem-32 169 42 . . PUNCT eurjchem-32 169 43     SPACE eurjchem-32 170 1 [ [ X eurjchem-32 170 2 7 7 NUM eurjchem-32 170 3 ] ] PUNCT eurjchem-32 170 4 . . PUNCT eurjchem-32 171 1 kappe kappe PROPN eurjchem-32 171 2 , , PUNCT eurjchem-32 171 3     SPACE eurjchem-32 171 4 t. t. PROPN eurjchem-32 171 5 ; ; PUNCT eurjchem-32 171 6     SPACE eurjchem-32 171 7 stelzel stelzel ADJ eurjchem-32 171 8 , , PUNCT eurjchem-32 171 9     SPACE eurjchem-32 171 10 h. h. PROPN eurjchem-32 171 11     SPACE eurjchem-32 171 12 p. p. NOUN eurjchem-32 171 13 ; ; PUNCT eurjchem-32 171 14     SPACE eurjchem-32 171 15 ziegler ziegler NOUN eurjchem-32 171 16 , , PUNCT eurjchem-32 171 17     SPACE eurjchem-32 171 18 e. e. PROPN eurjchem-32 171 19     SPACE eurjchem-32 171 20 monatsch monatsch PROPN eurjchem-32 171 21 . . PUNCT eurjchem-32 171 22     SPACE eurjchem-32 171 23 fur fur NOUN eurjchem-32 171 24     SPACE eurjchem-32 171 25 chem chem NOUN eurjchem-32 171 26 . . PUNCT eurjchem-32 171 27     SPACE eurjchem-32 171 28 1983 1983 NUM eurjchem-32 171 29 , , PUNCT eurjchem-32 171 30     SPACE eurjchem-32 171 31 114 114 NUM eurjchem-32 171 32 , , PUNCT eurjchem-32 171 33     SPACE eurjchem-32 171 34 953‐963 953‐963 NUM eurjchem-32 171 35 . . PUNCT eurjchem-32 171 36     SPACE eurjchem-32 172 1 [ [ X eurjchem-32 172 2 8 8 NUM eurjchem-32 172 3 ] ] PUNCT eurjchem-32 172 4 . . PUNCT eurjchem-32 173 1 stetinova stetinova PROPN eurjchem-32 173 2 , , PUNCT eurjchem-32 173 3     SPACE eurjchem-32 173 4 j. j. PROPN eurjchem-32 173 5 ; ; PUNCT eurjchem-32 173 6     SPACE eurjchem-32 173 7 kada kada PROPN eurjchem-32 173 8 , , PUNCT eurjchem-32 173 9     SPACE eurjchem-32 173 10 r. r. PROPN eurjchem-32 173 11 ; ; PUNCT eurjchem-32 173 12     SPACE eurjchem-32 173 13 lesko lesko PROPN eurjchem-32 173 14 , , PUNCT eurjchem-32 173 15     SPACE eurjchem-32 173 16 j. j. PROPN eurjchem-32 173 17 ; ; PUNCT eurjchem-32 173 18     SPACE eurjchem-32 173 19 zalibera zalibera NOUN eurjchem-32 173 20 , , PUNCT eurjchem-32 173 21     SPACE eurjchem-32 173 22 l. l. PROPN eurjchem-32 173 23 ; ; PUNCT eurjchem-32 173 24     SPACE eurjchem-32 173 25 ilavsky ilavsky NOUN eurjchem-32 173 26 , , PUNCT eurjchem-32 173 27     SPACE eurjchem-32 173 28 d. d. PROPN eurjchem-32 173 29     SPACE eurjchem-32 173 30 collect collect NOUN eurjchem-32 173 31 . . PUNCT eurjchem-32 173 32     SPACE eurjchem-32 173 33 czech czech PROPN eurjchem-32 173 34 . . PUNCT eurjchem-32 173 35     SPACE eurjchem-32 173 36 chem chem NOUN eurjchem-32 173 37 . . PUNCT eurjchem-32 173 38     SPACE eurjchem-32 174 1 c c NOUN eurjchem-32 174 2     SPACE eurjchem-32 174 3 1995 1995 NUM eurjchem-32 174 4 , , PUNCT eurjchem-32 174 5     SPACE eurjchem-32 174 6 60 60 NUM eurjchem-32 174 7 , , PUNCT eurjchem-32 174 8     SPACE eurjchem-32 174 9 999‐1008 999‐1008 NOUN eurjchem-32 174 10 . . PUNCT eurjchem-32 174 11     SPACE eurjchem-32 175 1 [ [ X eurjchem-32 175 2 9 9 NUM eurjchem-32 175 3 ] ] PUNCT eurjchem-32 175 4 . . PUNCT eurjchem-32 176 1 al‐lohedan al‐lohedan ADJ eurjchem-32 176 2 , , PUNCT eurjchem-32 176 3     SPACE eurjchem-32 176 4 h. h. PROPN eurjchem-32 176 5 ; ; PUNCT eurjchem-32 176 6     SPACE eurjchem-32 176 7 bunton bunton PROPN eurjchem-32 176 8 , , PUNCT eurjchem-32 176 9     SPACE eurjchem-32 176 10 c. c. PROPN eurjchem-32 176 11     SPACE eurjchem-32 176 12 a. a. PROPN eurjchem-32 176 13     SPACE eurjchem-32 176 14 j. j. PROPN eurjchem-32 176 15     SPACE eurjchem-32 176 16 org org PROPN eurjchem-32 176 17 . . PUNCT eurjchem-32 176 18     SPACE eurjchem-32 176 19 chem chem NOUN eurjchem-32 176 20 . . PUNCT eurjchem-32 176 21     SPACE eurjchem-32 176 22 1981 1981 NUM eurjchem-32 176 23 , , PUNCT eurjchem-32 176 24     SPACE eurjchem-32 176 25 46 46 NUM eurjchem-32 176 26 , , PUNCT eurjchem-32 176 27     SPACE eurjchem-32 176 28 3929‐3930 3929‐3930 NUM eurjchem-32 176 29 . . PUNCT eurjchem-32 176 30     SPACE eurjchem-32 177 1 [ [ X eurjchem-32 177 2 10 10 NUM eurjchem-32 177 3 ] ] PUNCT eurjchem-32 177 4 . . PUNCT eurjchem-32 178 1 fadda fadda PROPN eurjchem-32 178 2 , , PUNCT eurjchem-32 178 3     SPACE eurjchem-32 178 4 a. a. NOUN eurjchem-32 178 5     SPACE eurjchem-32 178 6 a. a. NOUN eurjchem-32 178 7 ; ; PUNCT eurjchem-32 178 8     SPACE eurjchem-32 178 9 abdelrazek abdelrazek NOUN eurjchem-32 178 10 , , PUNCT eurjchem-32 178 11     SPACE eurjchem-32 178 12 f. f. PROPN eurjchem-32 178 13     SPACE eurjchem-32 178 14 m. m. NOUN eurjchem-32 178 15 ; ; PUNCT eurjchem-32 178 16     SPACE eurjchem-32 178 17 el‐habbal el‐habbal ADJ eurjchem-32 178 18 , , PUNCT eurjchem-32 178 19     SPACE eurjchem-32 178 20 m. m. NOUN eurjchem-32 178 21     SPACE eurjchem-32 178 22 m. m. NOUN eurjchem-32 178 23     SPACE eurjchem-32 178 24 indian indian PROPN eurjchem-32 178 25     SPACE eurjchem-32 178 26 j. j. PROPN eurjchem-32 178 27     SPACE eurjchem-32 178 28 chem chem NOUN eurjchem-32 178 29 . . PUNCT eurjchem-32 178 30     SPACE eurjchem-32 178 31 1986 1986 NUM eurjchem-32 178 32 , , PUNCT eurjchem-32 178 33     SPACE eurjchem-32 178 34 25b 25b NOUN eurjchem-32 178 35 , , PUNCT eurjchem-32 178 36     SPACE eurjchem-32 178 37 194‐196 194‐196 NUM eurjchem-32 178 38 . . PUNCT eurjchem-32 178 39     SPACE eurjchem-32 179 1 [ [ X eurjchem-32 179 2 11 11 NUM eurjchem-32 179 3 ] ] PUNCT eurjchem-32 179 4 . . PUNCT eurjchem-32 180 1 abdelrazek abdelrazek PROPN eurjchem-32 180 2 , , PUNCT eurjchem-32 180 3     SPACE eurjchem-32 180 4 f. f. PROPN eurjchem-32 180 5     SPACE eurjchem-32 180 6 m. m. NOUN eurjchem-32 180 7 ; ; PUNCT eurjchem-32 180 8     SPACE eurjchem-32 180 9 fadda fadda NOUN eurjchem-32 180 10 , , PUNCT eurjchem-32 180 11     SPACE eurjchem-32 180 12 a. a. NOUN eurjchem-32 180 13     SPACE eurjchem-32 180 14 a. a. PROPN eurjchem-32 180 15       SPACE eurjchem-32 180 16 z. z. PROPN eurjchem-32 180 17     SPACE eurjchem-32 180 18 naturforsch naturforsch PROPN eurjchem-32 180 19 . . PUNCT eurjchem-32 180 20 , , PUNCT eurjchem-32 180 21     SPACE eurjchem-32 180 22 1986 1986 NUM eurjchem-32 180 23 , , PUNCT eurjchem-32 180 24     SPACE eurjchem-32 180 25 41b 41b NOUN eurjchem-32 180 26 , , PUNCT eurjchem-32 180 27     SPACE eurjchem-32 180 28 499‐501 499‐501 VERB eurjchem-32 180 29 . . PUNCT eurjchem-32 180 30     SPACE eurjchem-32 181 1 [ [ X eurjchem-32 181 2 12 12 NUM eurjchem-32 181 3 ] ] PUNCT eurjchem-32 181 4 . . PUNCT eurjchem-32 182 1 metwally metwally ADV eurjchem-32 182 2 , , PUNCT eurjchem-32 182 3     SPACE eurjchem-32 182 4 n. n. PROPN eurjchem-32 182 5     SPACE eurjchem-32 182 6 h. h. PROPN eurjchem-32 182 7 ; ; PUNCT eurjchem-32 182 8     SPACE eurjchem-32 182 9 abdelrazek abdelrazek NOUN eurjchem-32 182 10 , , PUNCT eurjchem-32 182 11     SPACE eurjchem-32 182 12 f. f. PROPN eurjchem-32 182 13     SPACE eurjchem-32 182 14 m. m. PROPN eurjchem-32 182 15     SPACE eurjchem-32 182 16 j. j. PROPN eurjchem-32 182 17     SPACE eurjchem-32 182 18 prakt prakt NOUN eurjchem-32 182 19 . . PUNCT eurjchem-32 182 20     SPACE eurjchem-32 183 1 chem chem NOUN eurjchem-32 183 2 . . PUNCT eurjchem-32 183 3     SPACE eurjchem-32 184 1 chem chem NOUN eurjchem-32 184 2 . . PUNCT eurjchem-32 184 3     SPACE eurjchem-32 185 1 zeitung zeitung PROPN eurjchem-32 185 2 ; ; PUNCT eurjchem-32 185 3     SPACE eurjchem-32 185 4 1998 1998 NUM eurjchem-32 185 5 , , PUNCT eurjchem-32 185 6     SPACE eurjchem-32 185 7 340 340 NUM eurjchem-32 185 8 , , PUNCT eurjchem-32 185 9     SPACE eurjchem-32 185 10 676‐678 676‐678 NUM eurjchem-32 185 11 . . PUNCT eurjchem-32 185 12     SPACE eurjchem-32 186 1 [ [ X eurjchem-32 186 2 13 13 NUM eurjchem-32 186 3 ] ] PUNCT eurjchem-32 186 4 . . PUNCT eurjchem-32 187 1 fadda fadda PROPN eurjchem-32 187 2 , , PUNCT eurjchem-32 187 3     SPACE eurjchem-32 187 4 a. a. NOUN eurjchem-32 187 5     SPACE eurjchem-32 187 6 a. a. NOUN eurjchem-32 187 7 ; ; PUNCT eurjchem-32 187 8     SPACE eurjchem-32 187 9 amer amer PROPN eurjchem-32 187 10 , , PUNCT eurjchem-32 187 11     SPACE eurjchem-32 187 12 f. f. PROPN eurjchem-32 187 13     SPACE eurjchem-32 187 14 a. a. NOUN eurjchem-32 187 15 ; ; PUNCT eurjchem-32 187 16     SPACE eurjchem-32 187 17 zaki zaki NOUN eurjchem-32 187 18 , , PUNCT eurjchem-32 187 19     SPACE eurjchem-32 187 20 m. m. NOUN eurjchem-32 187 21     SPACE eurjchem-32 187 22 e. e. PROPN eurjchem-32 187 23     SPACE eurjchem-32 187 24 a. a. PROPN eurjchem-32 187 25 ; ; PUNCT eurjchem-32 187 26     SPACE eurjchem-32 187 27 samir samir NOUN eurjchem-32 187 28 , , PUNCT eurjchem-32 187 29     SPACE eurjchem-32 187 30 k. k. NOUN eurjchem-32 187 31     SPACE eurjchem-32 187 32 phosphorus phosphorus NOUN eurjchem-32 187 33 , , PUNCT eurjchem-32 187 34     SPACE eurjchem-32 187 35 sulfur sulfur NOUN eurjchem-32 187 36 , , PUNCT eurjchem-32 187 37     SPACE eurjchem-32 187 38 silicon silicon NOUN eurjchem-32 187 39     SPACE eurjchem-32 187 40 & & CCONJ eurjchem-32 187 41     SPACE eurjchem-32 187 42 relat relat NOUN eurjchem-32 187 43 . . PUNCT eurjchem-32 187 44     SPACE eurjchem-32 188 1 elements element NOUN eurjchem-32 188 2     SPACE eurjchem-32 188 3 1999 1999 NUM eurjchem-32 188 4 , , PUNCT eurjchem-32 188 5     SPACE eurjchem-32 188 6 155 155 NUM eurjchem-32 188 7 , , PUNCT eurjchem-32 188 8     SPACE eurjchem-32 188 9 59‐66 59‐66 NOUN eurjchem-32 188 10 . . PUNCT eurjchem-32 188 11     SPACE eurjchem-32 189 1 [ [ X eurjchem-32 189 2 14 14 NUM eurjchem-32 189 3 ] ] PUNCT eurjchem-32 189 4 . . PUNCT eurjchem-32 190 1 abdelrazek abdelrazek PROPN eurjchem-32 190 2 , , PUNCT eurjchem-32 190 3     SPACE eurjchem-32 190 4 f. f. PROPN eurjchem-32 190 5     SPACE eurjchem-32 190 6 m. m. NOUN eurjchem-32 190 7 ; ; PUNCT eurjchem-32 190 8     SPACE eurjchem-32 190 9 metwally metwally ADV eurjchem-32 190 10 , , PUNCT eurjchem-32 190 11     SPACE eurjchem-32 190 12 n. n. PROPN eurjchem-32 190 13     SPACE eurjchem-32 190 14 h. h. PROPN eurjchem-32 190 15     SPACE eurjchem-32 190 16 syn syn PROPN eurjchem-32 190 17 . . PROPN eurjchem-32 190 18     SPACE eurjchem-32 190 19 commun commun PROPN eurjchem-32 190 20 . . PUNCT eurjchem-32 190 21     SPACE eurjchem-32 190 22 2009 2009 NUM eurjchem-32 190 23 , , PUNCT eurjchem-32 190 24     SPACE eurjchem-32 190 25 39 39 NUM eurjchem-32 190 26 , , PUNCT eurjchem-32 190 27     SPACE eurjchem-32 190 28 4088‐4099 4088‐4099 NUM eurjchem-32 190 29 . . PUNCT eurjchem-32 190 30     SPACE eurjchem-32 191 1 [ [ X eurjchem-32 191 2 15 15 NUM eurjchem-32 191 3 ] ] PUNCT eurjchem-32 191 4 . . PUNCT eurjchem-32 192 1 zaki zaki PROPN eurjchem-32 192 2 , , PUNCT eurjchem-32 192 3     SPACE eurjchem-32 192 4 m. m. NOUN eurjchem-32 192 5     SPACE eurjchem-32 192 6 e. e. PROPN eurjchem-32 192 7     SPACE eurjchem-32 192 8 a. a. PROPN eurjchem-32 192 9 ; ; PUNCT eurjchem-32 192 10     SPACE eurjchem-32 192 11 fadda fadda NOUN eurjchem-32 192 12 , , PUNCT eurjchem-32 192 13     SPACE eurjchem-32 192 14 a. a. NOUN eurjchem-32 192 15     SPACE eurjchem-32 192 16 a. a. NOUN eurjchem-32 192 17 ; ; PUNCT eurjchem-32 192 18     SPACE eurjchem-32 192 19 samir samir NOUN eurjchem-32 192 20 , , PUNCT eurjchem-32 192 21     SPACE eurjchem-32 192 22 k. k. PROPN eurjchem-32 192 23 ; ; PUNCT eurjchem-32 192 24     SPACE eurjchem-32 192 25 amer amer PROPN eurjchem-32 192 26 , , PUNCT eurjchem-32 192 27     SPACE eurjchem-32 192 28 f. f. PROPN eurjchem-32 192 29     SPACE eurjchem-32 192 30 a. a. NOUN eurjchem-32 192 31     SPACE eurjchem-32 192 32 phosphorus phosphorus NOUN eurjchem-32 192 33 , , PUNCT eurjchem-32 192 34     SPACE eurjchem-32 192 35 sulfur sulfur NOUN eurjchem-32 192 36 , , PUNCT eurjchem-32 192 37     SPACE eurjchem-32 192 38 silicon silicon NOUN eurjchem-32 192 39     SPACE eurjchem-32 192 40 & & CCONJ eurjchem-32 192 41     SPACE eurjchem-32 192 42 relat relat NOUN eurjchem-32 192 43 . . PUNCT eurjchem-32 192 44     SPACE eurjchem-32 192 45 elements element NOUN eurjchem-32 192 46     SPACE eurjchem-32 192 47 2006 2006 NUM eurjchem-32 192 48 , , PUNCT eurjchem-32 192 49     SPACE eurjchem-32 192 50 181 181 NUM eurjchem-32 192 51 , , PUNCT eurjchem-32 192 52     SPACE eurjchem-32 192 53 1815‐1823 1815‐1823 NUM eurjchem-32 192 54 . . PUNCT eurjchem-32 192 55     SPACE eurjchem-32 193 1 [ [ X eurjchem-32 193 2 16 16 NUM eurjchem-32 193 3 ] ] PUNCT eurjchem-32 193 4 . . PUNCT eurjchem-32 194 1 fadda fadda PROPN eurjchem-32 194 2 , , PUNCT eurjchem-32 194 3     SPACE eurjchem-32 194 4 a. a. NOUN eurjchem-32 194 5     SPACE eurjchem-32 194 6 a. a. NOUN eurjchem-32 194 7 ; ; PUNCT eurjchem-32 194 8     SPACE eurjchem-32 194 9 zaki zaki NOUN eurjchem-32 194 10 , , PUNCT eurjchem-32 194 11     SPACE eurjchem-32 194 12 m. m. NOUN eurjchem-32 194 13     SPACE eurjchem-32 194 14 e. e. PROPN eurjchem-32 194 15     SPACE eurjchem-32 194 16 a. a. PROPN eurjchem-32 194 17 ; ; PUNCT eurjchem-32 194 18     SPACE eurjchem-32 194 19 samir samir NOUN eurjchem-32 194 20 , , PUNCT eurjchem-32 194 21     SPACE eurjchem-32 194 22 k. k. PROPN eurjchem-32 194 23 ; ; PUNCT eurjchem-32 194 24     SPACE eurjchem-32 194 25 amer amer PROPN eurjchem-32 194 26 , , PUNCT eurjchem-32 194 27     SPACE eurjchem-32 194 28 f. f. PROPN eurjchem-32 194 29     SPACE eurjchem-32 194 30 a. a. NOUN eurjchem-32 194 31     SPACE eurjchem-32 194 32 phosphorus phosphorus NOUN eurjchem-32 194 33 , , PUNCT eurjchem-32 194 34     SPACE eurjchem-32 194 35 sulfur sulfur NOUN eurjchem-32 194 36 , , PUNCT eurjchem-32 194 37     SPACE eurjchem-32 194 38 silicon silicon NOUN eurjchem-32 194 39     SPACE eurjchem-32 194 40 & & CCONJ eurjchem-32 194 41     SPACE eurjchem-32 194 42 relat relat NOUN eurjchem-32 194 43 . . PUNCT eurjchem-32 194 44     SPACE eurjchem-32 195 1 elements element NOUN eurjchem-32 195 2     SPACE eurjchem-32 195 3 2007 2007 NUM eurjchem-32 195 4 , , PUNCT eurjchem-32 195 5     SPACE eurjchem-32 195 6 182 182 NUM eurjchem-32 195 7 , , PUNCT eurjchem-32 195 8     SPACE eurjchem-32 195 9 1845‐1856 1845‐1856 NUM eurjchem-32 195 10 . . PUNCT eurjchem-32 195 11     SPACE eurjchem-32 196 1 [ [ X eurjchem-32 196 2 17 17 NUM eurjchem-32 196 3 ] ] PUNCT eurjchem-32 196 4 . . PUNCT eurjchem-32 197 1 abdelrazek abdelrazek PROPN eurjchem-32 197 2 , , PUNCT eurjchem-32 197 3     SPACE eurjchem-32 197 4 f. f. PROPN eurjchem-32 197 5     SPACE eurjchem-32 197 6 m. m. NOUN eurjchem-32 197 7 ; ; PUNCT eurjchem-32 197 8     SPACE eurjchem-32 197 9 metwally metwally ADV eurjchem-32 197 10 , , PUNCT eurjchem-32 197 11     SPACE eurjchem-32 197 12 n. n. PROPN eurjchem-32 197 13     SPACE eurjchem-32 197 14 h. h. PROPN eurjchem-32 197 15 ; ; PUNCT eurjchem-32 197 16     SPACE eurjchem-32 197 17 sobhy sobhy NOUN eurjchem-32 197 18 , , PUNCT eurjchem-32 197 19     SPACE eurjchem-32 197 20 n. n. NOUN eurjchem-32 197 21     SPACE eurjchem-32 197 22 a. a. NOUN eurjchem-32 197 23     SPACE eurjchem-32 197 24 afinidad afinidad PROPN eurjchem-32 197 25     SPACE eurjchem-32 197 26 2008 2008 NUM eurjchem-32 197 27 , , PUNCT eurjchem-32 197 28     SPACE eurjchem-32 197 29 65(538 65(538 NOUN eurjchem-32 197 30 ) ) PUNCT eurjchem-32 197 31 , , PUNCT eurjchem-32 197 32     SPACE eurjchem-32 197 33 482‐487 482‐487 PROPN eurjchem-32 197 34 . . PUNCT eurjchem-32 197 35     SPACE eurjchem-32 198 1 [ [ X eurjchem-32 198 2 18 18 NUM eurjchem-32 198 3 ] ] PUNCT eurjchem-32 198 4 . . PUNCT eurjchem-32 199 1 abdelrazek abdelrazek PROPN eurjchem-32 199 2 , , PUNCT eurjchem-32 199 3     SPACE eurjchem-32 199 4 f. f. PROPN eurjchem-32 199 5     SPACE eurjchem-32 199 6 m. m. NOUN eurjchem-32 199 7 ; ; PUNCT eurjchem-32 199 8     SPACE eurjchem-32 199 9 metwally metwally ADV eurjchem-32 199 10 , , PUNCT eurjchem-32 199 11     SPACE eurjchem-32 199 12 n. n. PROPN eurjchem-32 199 13     SPACE eurjchem-32 199 14 h. h. PROPN eurjchem-32 199 15 ; ; PUNCT eurjchem-32 199 16     SPACE eurjchem-32 199 17 kassab kassab VERB eurjchem-32 199 18 , , PUNCT eurjchem-32 199 19     SPACE eurjchem-32 199 20 n. n. NOUN eurjchem-32 199 21     SPACE eurjchem-32 199 22 a. a. NOUN eurjchem-32 199 23 ; ; PUNCT eurjchem-32 199 24     SPACE eurjchem-32 199 25 sobhy sobhy NOUN eurjchem-32 199 26 , , PUNCT eurjchem-32 199 27     SPACE eurjchem-32 199 28 n. n. NOUN eurjchem-32 199 29     SPACE eurjchem-32 199 30 a. a. NOUN eurjchem-32 199 31     SPACE eurjchem-32 199 32 j. j. PROPN eurjchem-32 199 33     SPACE eurjchem-32 199 34 heterocyclic heterocyclic ADJ eurjchem-32 199 35     SPACE eurjchem-32 199 36 chem chem NOUN eurjchem-32 199 37 . . PUNCT eurjchem-32 199 38     SPACE eurjchem-32 199 39 2009 2009 NUM eurjchem-32 199 40 , , PUNCT eurjchem-32 199 41     SPACE eurjchem-32 199 42 46 46 NUM eurjchem-32 199 43 , , PUNCT eurjchem-32 199 44     SPACE eurjchem-32 199 45 1380‐1385 1380‐1385 NUM eurjchem-32 199 46 . . PUNCT eurjchem-32 199 47     SPACE eurjchem-32 200 1 [ [ X eurjchem-32 200 2 19 19 NUM eurjchem-32 200 3 ] ] PUNCT eurjchem-32 200 4 . . PUNCT eurjchem-32 200 5 abdelrazek abdelrazek PROPN eurjchem-32 200 6 , , PUNCT eurjchem-32 200 7     SPACE eurjchem-32 200 8 f. f. PROPN eurjchem-32 200 9     SPACE eurjchem-32 200 10 m. m. NOUN eurjchem-32 200 11 ; ; PUNCT eurjchem-32 200 12     SPACE eurjchem-32 200 13 elsayed elsaye VERB eurjchem-32 200 14 , , PUNCT eurjchem-32 200 15     SPACE eurjchem-32 200 16 a. a. NOUN eurjchem-32 200 17     SPACE eurjchem-32 200 18 n. n. PROPN eurjchem-32 200 19     SPACE eurjchem-32 200 20 j. j. PROPN eurjchem-32 200 21     SPACE eurjchem-32 200 22 heterocyclic heterocyclic ADJ eurjchem-32 200 23     SPACE eurjchem-32 200 24 chem chem NOUN eurjchem-32 200 25 . . PUNCT eurjchem-32 200 26         SPACE eurjchem-32 200 27 2009 2009 NUM eurjchem-32 200 28 , , PUNCT eurjchem-32 200 29     SPACE eurjchem-32 200 30 46 46 NUM eurjchem-32 200 31 , , PUNCT eurjchem-32 200 32     SPACE eurjchem-32 200 33 949‐ 949‐ NUM eurjchem-32 200 34 953 953 NUM eurjchem-32 200 35 . . PUNCT eurjchem-32 200 36     SPACE eurjchem-32 201 1 [ [ X eurjchem-32 201 2 20 20 NUM eurjchem-32 201 3 ] ] PUNCT eurjchem-32 201 4 . . PUNCT eurjchem-32 201 5 abdelrazek abdelrazek PROPN eurjchem-32 201 6 , , PUNCT eurjchem-32 201 7     SPACE eurjchem-32 201 8 f. f. PROPN eurjchem-32 201 9     SPACE eurjchem-32 201 10 m. m. NOUN eurjchem-32 201 11 ; ; PUNCT eurjchem-32 201 12     SPACE eurjchem-32 201 13 fadda fadda NOUN eurjchem-32 201 14 , , PUNCT eurjchem-32 201 15     SPACE eurjchem-32 201 16 a. a. NOUN eurjchem-32 201 17     SPACE eurjchem-32 201 18 a. a. NOUN eurjchem-32 201 19 ; ; PUNCT eurjchem-32 201 20     SPACE eurjchem-32 201 21 elsayed elsaye VERB eurjchem-32 201 22 , , PUNCT eurjchem-32 201 23     SPACE eurjchem-32 201 24 a. a. NOUN eurjchem-32 201 25     SPACE eurjchem-32 201 26 n. n. PROPN eurjchem-32 201 27     SPACE eurjchem-32 201 28 syn syn PROPN eurjchem-32 201 29 . . PROPN eurjchem-32 201 30     SPACE eurjchem-32 201 31 commun commun PROPN eurjchem-32 201 32 . . PUNCT eurjchem-32 201 33     SPACE eurjchem-32 201 34 2010 2010 NUM eurjchem-32 201 35 , , PUNCT eurjchem-32 201 36     SPACE eurjchem-32 201 37 ( ( PUNCT eurjchem-32 201 38 lsyc‐2009‐3951 lsyc‐2009‐3951 NOUN eurjchem-32 201 39 ) ) PUNCT eurjchem-32 201 40 , , PUNCT eurjchem-32 201 41     SPACE eurjchem-32 201 42 in in ADP eurjchem-32 201 43     SPACE eurjchem-32 201 44 press press NOUN eurjchem-32 201 45 . . PUNCT eurjchem-32 201 46     SPACE eurjchem-32 202 1 [ [ X eurjchem-32 202 2 21 21 NUM eurjchem-32 202 3 ] ] PUNCT eurjchem-32 202 4 . . PUNCT eurjchem-32 203 1 abdel‐latif abdel‐latif PROPN eurjchem-32 203 2 , , PUNCT eurjchem-32 203 3     SPACE eurjchem-32 203 4 e. e. PROPN eurjchem-32 203 5 ; ; PUNCT eurjchem-32 203 6     SPACE eurjchem-32 203 7 mustafa mustafa PROPN eurjchem-32 203 8 , , PUNCT eurjchem-32 203 9     SPACE eurjchem-32 203 10 h. h. PROPN eurjchem-32 203 11     SPACE eurjchem-32 203 12 m. m. NOUN eurjchem-32 203 13 ; ; PUNCT eurjchem-32 203 14     SPACE eurjchem-32 203 15 etman etman NOUN eurjchem-32 203 16 , , PUNCT eurjchem-32 203 17     SPACE eurjchem-32 203 18 h. h. PROPN eurjchem-32 203 19     SPACE eurjchem-32 203 20 a. a. NOUN eurjchem-32 203 21 ; ; PUNCT eurjchem-32 203 22     SPACE eurjchem-32 203 23 fadda fadda NOUN eurjchem-32 203 24 , , PUNCT eurjchem-32 203 25     SPACE eurjchem-32 203 26 a. a. NOUN eurjchem-32 203 27     SPACE eurjchem-32 203 28 a. a. NOUN eurjchem-32 203 29     SPACE eurjchem-32 203 30 russ russ PROPN eurjchem-32 203 31 . . PUNCT eurjchem-32 203 32     SPACE eurjchem-32 203 33 j. j. PROPN eurjchem-32 203 34     SPACE eurjchem-32 203 35 org org PROPN eurjchem-32 203 36 . . PUNCT eurjchem-32 203 37     SPACE eurjchem-32 203 38 chem chem NOUN eurjchem-32 203 39 . . PUNCT eurjchem-32 203 40     SPACE eurjchem-32 203 41 2007 2007 NUM eurjchem-32 203 42 , , PUNCT eurjchem-32 203 43     SPACE eurjchem-32 203 44 43 43 NUM eurjchem-32 203 45 , , PUNCT eurjchem-32 203 46     SPACE eurjchem-32 203 47 443‐448 443‐448 PROPN eurjchem-32 203 48 . . PUNCT eurjchem-32 203 49     SPACE eurjchem-32 204 1 [ [ X eurjchem-32 204 2 22 22 NUM eurjchem-32 204 3 ] ] PUNCT eurjchem-32 204 4 . . PUNCT eurjchem-32 205 1 fadda fadda PROPN eurjchem-32 205 2 , , PUNCT eurjchem-32 205 3     SPACE eurjchem-32 205 4 a. a. NOUN eurjchem-32 205 5     SPACE eurjchem-32 205 6 a. a. NOUN eurjchem-32 205 7 ; ; PUNCT eurjchem-32 205 8     SPACE eurjchem-32 205 9 abdel‐latif abdel‐latif PROPN eurjchem-32 205 10 , , PUNCT eurjchem-32 205 11     SPACE eurjchem-32 205 12 e. e. PROPN eurjchem-32 205 13 ; ; PUNCT eurjchem-32 205 14     SPACE eurjchem-32 205 15 bondock bondock NOUN eurjchem-32 205 16 , , PUNCT eurjchem-32 205 17     SPACE eurjchem-32 205 18 s. s. PROPN eurjchem-32 205 19 ; ; PUNCT eurjchem-32 205 20     SPACE eurjchem-32 205 21 samir samir NOUN eurjchem-32 205 22 , , PUNCT eurjchem-32 205 23     SPACE eurjchem-32 205 24 a. a. NOUN eurjchem-32 205 25     SPACE eurjchem-32 205 26 syn syn PROPN eurjchem-32 205 27 . . PROPN eurjchem-32 205 28     SPACE eurjchem-32 205 29 commun commun PROPN eurjchem-32 205 30 . . PUNCT eurjchem-32 205 31     SPACE eurjchem-32 205 32 2008 2008 NUM eurjchem-32 205 33 , , PUNCT eurjchem-32 205 34     SPACE eurjchem-32 205 35 38 38 NUM eurjchem-32 205 36 , , PUNCT eurjchem-32 205 37     SPACE eurjchem-32 205 38 4352‐4368 4352‐4368 NOUN eurjchem-32 205 39 . . PUNCT eurjchem-32 205 40     SPACE eurjchem-32 206 1 [ [ X eurjchem-32 206 2 23 23 NUM eurjchem-32 206 3 ] ] PUNCT eurjchem-32 206 4 . . PUNCT eurjchem-32 207 1 fadda fadda PROPN eurjchem-32 207 2 , , PUNCT eurjchem-32 207 3     SPACE eurjchem-32 207 4 a. a. NOUN eurjchem-32 207 5     SPACE eurjchem-32 207 6 a. a. NOUN eurjchem-32 207 7 ; ; PUNCT eurjchem-32 207 8     SPACE eurjchem-32 207 9 el‐zemaity el‐zemaity NOUN eurjchem-32 207 10 , , PUNCT eurjchem-32 207 11     SPACE eurjchem-32 207 12 m. m. NOUN eurjchem-32 207 13     SPACE eurjchem-32 207 14 t. t. PROPN eurjchem-32 207 15 ; ; PUNCT eurjchem-32 207 16     SPACE eurjchem-32 207 17 gerges gerge NOUN eurjchem-32 207 18 , , PUNCT eurjchem-32 207 19     SPACE eurjchem-32 207 20 m. m. NOUN eurjchem-32 207 21     SPACE eurjchem-32 207 22 m. m. NOUN eurjchem-32 207 23 ; ; PUNCT eurjchem-32 207 24     SPACE eurjchem-32 207 25 refat refat NOUN eurjchem-32 207 26 , , PUNCT eurjchem-32 207 27     SPACE eurjchem-32 207 28 h. h. PROPN eurjchem-32 207 29     SPACE eurjchem-32 207 30 m. m. NOUN eurjchem-32 207 31 ; ; PUNCT eurjchem-32 207 32     SPACE eurjchem-32 207 33 biehl biehl PROPN eurjchem-32 207 34     SPACE eurjchem-32 207 35 e. e. PROPN eurjchem-32 207 36     SPACE eurjchem-32 207 37 r. r. PROPN eurjchem-32 207 38     SPACE eurjchem-32 207 39 heterocycles heterocycle NOUN eurjchem-32 207 40     SPACE eurjchem-32 207 41 1996 1996 NUM eurjchem-32 207 42 , , PUNCT eurjchem-32 207 43     SPACE eurjchem-32 207 44 43 43 NUM eurjchem-32 207 45 , , PUNCT eurjchem-32 207 46     SPACE eurjchem-32 207 47 23‐32 23‐32 NUM eurjchem-32 207 48 . . PUNCT eurjchem-32 207 49                                                                             SPACE