id sid tid token lemma pos eurjchem-91 1 1 microsoft microsoft PROPN eurjchem-91 1 2 word word PROPN eurjchem-91 1 3 european_journal_of_chemistry_1_3_2010_195_199_91 european_journal_of_chemistry_1_3_2010_195_199_91 PROPN eurjchem-91 1 4 european european ADJ eurjchem-91 1 5     SPACE eurjchem-91 1 6 journal journal NOUN eurjchem-91 1 7     SPACE eurjchem-91 1 8 of of ADP eurjchem-91 1 9     SPACE eurjchem-91 1 10 chemistry chemistry NOUN eurjchem-91 1 11     SPACE eurjchem-91 1 12 1 1 NUM eurjchem-91 1 13     SPACE eurjchem-91 1 14 ( ( PUNCT eurjchem-91 1 15 3 3 NUM eurjchem-91 1 16 ) ) PUNCT eurjchem-91 1 17     SPACE eurjchem-91 1 18 ( ( PUNCT eurjchem-91 1 19 2010 2010 NUM eurjchem-91 1 20 ) ) PUNCT eurjchem-91 1 21     SPACE eurjchem-91 1 22 195‐199 195‐199 PROPN eurjchem-91 1 23         SPACE eurjchem-91 1 24 european european ADJ eurjchem-91 1 25     SPACE eurjchem-91 1 26 journal journal NOUN eurjchem-91 1 27     SPACE eurjchem-91 1 28 of of ADP eurjchem-91 1 29     SPACE eurjchem-91 1 30 chemistry chemistry NOUN eurjchem-91 1 31     SPACE eurjchem-91 1 32 issn issn VERB eurjchem-91 1 33     SPACE eurjchem-91 1 34 2153‐2249 2153‐2249 NUM eurjchem-91 1 35     SPACE eurjchem-91 1 36 ( ( PUNCT eurjchem-91 1 37 print print NOUN eurjchem-91 1 38 ) ) PUNCT eurjchem-91 1 39     SPACE eurjchem-91 1 40 / / SYM eurjchem-91 1 41     SPACE eurjchem-91 1 42 issn issn VERB eurjchem-91 1 43     SPACE eurjchem-91 1 44 2153‐2257 2153‐2257 NUM eurjchem-91 1 45     SPACE eurjchem-91 1 46 ( ( PUNCT eurjchem-91 1 47 online online ADJ eurjchem-91 1 48 ) ) PUNCT eurjchem-91 1 49     SPACE eurjchem-91 1 50   NOUN eurjchem-91 1 51     SPACE eurjchem-91 1 52 2010 2010 NUM eurjchem-91 1 53     SPACE eurjchem-91 1 54 eurjchem eurjchem NOUN eurjchem-91 1 55     SPACE eurjchem-91 1 56 doi:10.5155 doi:10.5155 PROPN eurjchem-91 1 57 / / SYM eurjchem-91 1 58 eurjchem.1.3.195‐199.91 eurjchem.1.3.195‐199.91 NOUN eurjchem-91 1 59                 SPACE eurjchem-91 1 60 european european ADJ eurjchem-91 1 61     SPACE eurjchem-91 1 62 journal journal NOUN eurjchem-91 1 63     SPACE eurjchem-91 1 64 of of ADP eurjchem-91 1 65     SPACE eurjchem-91 1 66 chemistry chemistry NOUN eurjchem-91 1 67     SPACE eurjchem-91 1 68 journal journal NOUN eurjchem-91 1 69     SPACE eurjchem-91 1 70 homepage homepage NOUN eurjchem-91 1 71 : : PUNCT eurjchem-91 1 72     SPACE eurjchem-91 1 73 www.eurjchem.com www.eurjchem.com NOUN eurjchem-91 1 74                     SPACE eurjchem-91 1 75 novel novel NOUN eurjchem-91 1 76     SPACE eurjchem-91 1 77 heterocyclic heterocyclic NOUN eurjchem-91 1 78     SPACE eurjchem-91 1 79 derivatives derivative NOUN eurjchem-91 1 80     SPACE eurjchem-91 1 81 of of ADP eurjchem-91 1 82     SPACE eurjchem-91 1 83 pyrano[3,2‐c]quinolinone pyrano[3,2‐c]quinolinone NOUN eurjchem-91 1 84     SPACE eurjchem-91 1 85 from from ADP eurjchem-91 1 86       SPACE eurjchem-91 1 87 3‐(1‐ethy1‐4‐hydroxy‐2‐oxo‐2(1h)‐quinolin‐3‐yl)‐3‐oxopropanoic 3‐(1‐ethy1‐4‐hydroxy‐2‐oxo‐2(1h)‐quinolin‐3‐yl)‐3‐oxopropanoic PROPN eurjchem-91 1 88     SPACE eurjchem-91 1 89 acid acid ADJ eurjchem-91 1 90     SPACE eurjchem-91 1 91 magdy magdy NOUN eurjchem-91 1 92     SPACE eurjchem-91 1 93 ahmed ahmed PROPN eurjchem-91 1 94     SPACE eurjchem-91 1 95 ibrahim ibrahim PROPN eurjchem-91 1 96 * * PROPN eurjchem-91 1 97 , , PUNCT eurjchem-91 1 98     SPACE eurjchem-91 1 99 hany hany PROPN eurjchem-91 1 100     SPACE eurjchem-91 1 101 mohamed mohamed PROPN eurjchem-91 1 102     SPACE eurjchem-91 1 103 hassanin hassanin PROPN eurjchem-91 1 104 , , PUNCT eurjchem-91 1 105       SPACE eurjchem-91 1 106 yassin yassin PROPN eurjchem-91 1 107     SPACE eurjchem-91 1 108 abdel‐allah abdel‐allah PROPN eurjchem-91 1 109     SPACE eurjchem-91 1 110 gabr gabr NOUN eurjchem-91 1 111     SPACE eurjchem-91 1 112 and and CCONJ eurjchem-91 1 113     SPACE eurjchem-91 1 114 youssef youssef PROPN eurjchem-91 1 115     SPACE eurjchem-91 1 116 abdel‐salam abdel‐salam PROPN eurjchem-91 1 117     SPACE eurjchem-91 1 118 alnamer alnamer NOUN eurjchem-91 1 119     SPACE eurjchem-91 1 120 department department NOUN eurjchem-91 1 121     SPACE eurjchem-91 1 122 of of ADP eurjchem-91 1 123     SPACE eurjchem-91 1 124 chemistry chemistry NOUN eurjchem-91 1 125 , , PUNCT eurjchem-91 1 126     SPACE eurjchem-91 1 127 faculty faculty NOUN eurjchem-91 1 128     SPACE eurjchem-91 1 129 of of ADP eurjchem-91 1 130     SPACE eurjchem-91 1 131 education education NOUN eurjchem-91 1 132 , , PUNCT eurjchem-91 1 133     SPACE eurjchem-91 1 134 ain ain PROPN eurjchem-91 1 135     SPACE eurjchem-91 1 136 shams sham NOUN eurjchem-91 1 137     SPACE eurjchem-91 1 138 university university NOUN eurjchem-91 1 139 , , PUNCT eurjchem-91 1 140     SPACE eurjchem-91 1 141 roxy roxy PROPN eurjchem-91 1 142     SPACE eurjchem-91 1 143 11711 11711 NUM eurjchem-91 1 144 , , PUNCT eurjchem-91 1 145     SPACE eurjchem-91 1 146 cairo cairo PROPN eurjchem-91 1 147 , , PUNCT eurjchem-91 1 148     SPACE eurjchem-91 1 149 egypt egypt PROPN eurjchem-91 1 150     SPACE eurjchem-91 1 151 * * PROPN eurjchem-91 1 152 corresponding corresponding ADJ eurjchem-91 1 153     SPACE eurjchem-91 1 154 author author NOUN eurjchem-91 1 155     SPACE eurjchem-91 1 156 at at ADP eurjchem-91 1 157 : : PUNCT eurjchem-91 1 158     SPACE eurjchem-91 1 159 department department NOUN eurjchem-91 1 160     SPACE eurjchem-91 1 161 of of ADP eurjchem-91 1 162     SPACE eurjchem-91 1 163 chemistry chemistry NOUN eurjchem-91 1 164 , , PUNCT eurjchem-91 1 165     SPACE eurjchem-91 1 166 faculty faculty NOUN eurjchem-91 1 167     SPACE eurjchem-91 1 168 of of ADP eurjchem-91 1 169     SPACE eurjchem-91 1 170 education education NOUN eurjchem-91 1 171 , , PUNCT eurjchem-91 1 172     SPACE eurjchem-91 1 173 ain ain PROPN eurjchem-91 1 174     SPACE eurjchem-91 1 175 shams sham NOUN eurjchem-91 1 176     SPACE eurjchem-91 1 177 university university NOUN eurjchem-91 1 178 , , PUNCT eurjchem-91 1 179     SPACE eurjchem-91 1 180 roxy roxy PROPN eurjchem-91 1 181     SPACE eurjchem-91 1 182 11711 11711 NUM eurjchem-91 1 183 , , PUNCT eurjchem-91 1 184     SPACE eurjchem-91 1 185 cairo cairo PROPN eurjchem-91 1 186 , , PUNCT eurjchem-91 1 187     SPACE eurjchem-91 1 188 egypt egypt PROPN eurjchem-91 1 189 . . PUNCT eurjchem-91 1 190     SPACE eurjchem-91 2 1 tel tel PROPN eurjchem-91 2 2 . . PUNCT eurjchem-91 2 3 : : PUNCT eurjchem-91 2 4     SPACE eurjchem-91 2 5 +20107887204 +20107887204 ADJ eurjchem-91 2 6 ; ; PUNCT eurjchem-91 2 7     SPACE eurjchem-91 2 8 fax fax NOUN eurjchem-91 2 9 : : PUNCT eurjchem-91 2 10     SPACE eurjchem-91 2 11 +2022581243 +2022581243 NOUN eurjchem-91 2 12 . . PUNCT eurjchem-91 2 13     SPACE eurjchem-91 2 14 e­mail e­mail NOUN eurjchem-91 2 15     SPACE eurjchem-91 2 16 address address NOUN eurjchem-91 2 17 : : PUNCT eurjchem-91 2 18 magdy_ahmed1977@yahoo.com magdy_ahmed1977@yahoo.com X eurjchem-91 2 19     SPACE eurjchem-91 2 20 ( ( PUNCT eurjchem-91 2 21 m.a m.a PROPN eurjchem-91 2 22 . . PROPN eurjchem-91 2 23     SPACE eurjchem-91 2 24 ibrahim ibrahim PROPN eurjchem-91 2 25 ) ) PUNCT eurjchem-91 2 26 . . PUNCT eurjchem-91 2 27                                 SPACE eurjchem-91 3 1 article article NOUN eurjchem-91 3 2     SPACE eurjchem-91 3 3 information information NOUN eurjchem-91 3 4         SPACE eurjchem-91 3 5 abstract abstract ADJ eurjchem-91 3 6 received receive VERB eurjchem-91 3 7 : : PUNCT eurjchem-91 3 8     SPACE eurjchem-91 3 9 9 9 NUM eurjchem-91 3 10     SPACE eurjchem-91 3 11 march march PROPN eurjchem-91 3 12     SPACE eurjchem-91 3 13 2010 2010 NUM eurjchem-91 3 14     SPACE eurjchem-91 3 15 received receive VERB eurjchem-91 3 16     SPACE eurjchem-91 3 17 in in ADP eurjchem-91 3 18     SPACE eurjchem-91 3 19 revised revise VERB eurjchem-91 3 20     SPACE eurjchem-91 3 21 form form NOUN eurjchem-91 3 22 : : PUNCT eurjchem-91 3 23     SPACE eurjchem-91 3 24 5 5 NUM eurjchem-91 3 25     SPACE eurjchem-91 3 26 may may AUX eurjchem-91 3 27     SPACE eurjchem-91 3 28 2010 2010 NUM eurjchem-91 3 29     SPACE eurjchem-91 3 30 accepted accept VERB eurjchem-91 3 31 : : PUNCT eurjchem-91 3 32     SPACE eurjchem-91 3 33 8 8 NUM eurjchem-91 3 34     SPACE eurjchem-91 3 35 june june PROPN eurjchem-91 3 36     SPACE eurjchem-91 3 37 2010 2010 NUM eurjchem-91 3 38     SPACE eurjchem-91 3 39 online online NOUN eurjchem-91 3 40 : : PUNCT eurjchem-91 3 41     SPACE eurjchem-91 3 42 30 30 NUM eurjchem-91 3 43     SPACE eurjchem-91 3 44 september september PROPN eurjchem-91 3 45       SPACE eurjchem-91 3 46 2010 2010 NUM eurjchem-91 3 47     SPACE eurjchem-91 3 48 keywords keyword VERB eurjchem-91 3 49         SPACE eurjchem-91 3 50 3‐(1‐ethyl‐4‐hydroxy‐2‐oxo‐2(1h)‐quinolin‐3‐yl)‐3‐oxopropanoic 3‐(1‐ethyl‐4‐hydroxy‐2‐oxo‐2(1h)‐quinolin‐3‐yl)‐3‐oxopropanoic NUM eurjchem-91 3 51     SPACE eurjchem-91 3 52 acid acid NOUN eurjchem-91 3 53     SPACE eurjchem-91 3 54 ( ( PUNCT eurjchem-91 3 55 2 2 NUM eurjchem-91 3 56 ) ) PUNCT eurjchem-91 3 57     SPACE eurjchem-91 3 58 has have AUX eurjchem-91 3 59     SPACE eurjchem-91 3 60 been be AUX eurjchem-91 3 61 synthesized synthesize VERB eurjchem-91 3 62 . . PUNCT eurjchem-91 3 63     SPACE eurjchem-91 3 64 the the DET eurjchem-91 3 65     SPACE eurjchem-91 3 66 chemical chemical NOUN eurjchem-91 3 67     SPACE eurjchem-91 3 68 behaviour behaviour NOUN eurjchem-91 3 69     SPACE eurjchem-91 3 70 of of ADP eurjchem-91 3 71     SPACE eurjchem-91 3 72 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 3 73     SPACE eurjchem-91 3 74 2 2 NUM eurjchem-91 3 75     SPACE eurjchem-91 3 76 was be AUX eurjchem-91 3 77     SPACE eurjchem-91 3 78 studied study VERB eurjchem-91 3 79     SPACE eurjchem-91 3 80 towards towards ADP eurjchem-91 3 81     SPACE eurjchem-91 3 82 condensation condensation NOUN eurjchem-91 3 83 reactions reaction NOUN eurjchem-91 3 84     SPACE eurjchem-91 3 85 with with ADP eurjchem-91 3 86     SPACE eurjchem-91 3 87 salicylaldelyde salicylaldelyde NOUN eurjchem-91 3 88 , , PUNCT eurjchem-91 3 89     SPACE eurjchem-91 3 90 2‐hydroxy‐1‐naphthaldehyde 2‐hydroxy‐1‐naphthaldehyde NOUN eurjchem-91 3 91 , , PUNCT eurjchem-91 3 92     SPACE eurjchem-91 3 93 1‐phenyl‐4‐hydroxy‐2‐oxo‐ 1‐phenyl‐4‐hydroxy‐2‐oxo‐ NUM eurjchem-91 3 94 quinoline‐3‐carboxaldehyde quinoline‐3‐carboxaldehyde PROPN eurjchem-91 3 95 , , PUNCT eurjchem-91 3 96     SPACE eurjchem-91 3 97 2‐hydroxy‐4‐oxo‐4h‐pyrido[1,2‐a]pyrimidine‐3‐carboxalde‐ 2‐hydroxy‐4‐oxo‐4h‐pyrido[1,2‐a]pyrimidine‐3‐carboxalde‐ NUM eurjchem-91 3 98 hyde hyde NOUN eurjchem-91 3 99 , , PUNCT eurjchem-91 3 100     SPACE eurjchem-91 3 101 2‐amino‐3‐formylchromone 2‐amino‐3‐formylchromone NUM eurjchem-91 3 102     SPACE eurjchem-91 3 103 and and CCONJ eurjchem-91 3 104     SPACE eurjchem-91 3 105 its its PRON eurjchem-91 3 106     SPACE eurjchem-91 3 107 8‐allyl 8‐allyl NUM eurjchem-91 3 108     SPACE eurjchem-91 3 109 analog analog NOUN eurjchem-91 3 110 , , PUNCT eurjchem-91 3 111     SPACE eurjchem-91 3 112 3‐cyanochromone 3‐cyanochromone NOUN eurjchem-91 3 113     SPACE eurjchem-91 3 114 and and CCONJ eurjchem-91 3 115     SPACE eurjchem-91 3 116 its its PRON eurjchem-91 3 117     SPACE eurjchem-91 3 118 8‐allyl 8‐allyl NUM eurjchem-91 3 119 analog analog NOUN eurjchem-91 3 120 . . PUNCT eurjchem-91 3 121     SPACE eurjchem-91 4 1 structures structure NOUN eurjchem-91 4 2     SPACE eurjchem-91 4 3 of of ADP eurjchem-91 4 4     SPACE eurjchem-91 4 5 the the DET eurjchem-91 4 6     SPACE eurjchem-91 4 7 newly newly ADV eurjchem-91 4 8     SPACE eurjchem-91 4 9 synthesized synthesize VERB eurjchem-91 4 10     SPACE eurjchem-91 4 11 products product NOUN eurjchem-91 4 12     SPACE eurjchem-91 4 13 have have AUX eurjchem-91 4 14     SPACE eurjchem-91 4 15 been be AUX eurjchem-91 4 16     SPACE eurjchem-91 4 17 deduced deduce VERB eurjchem-91 4 18     SPACE eurjchem-91 4 19 from from ADP eurjchem-91 4 20     SPACE eurjchem-91 4 21 their their PRON eurjchem-91 4 22     SPACE eurjchem-91 4 23 elemental elemental ADJ eurjchem-91 4 24 analysis analysis NOUN eurjchem-91 4 25     SPACE eurjchem-91 4 26 and and CCONJ eurjchem-91 4 27     SPACE eurjchem-91 4 28 spectral spectral ADJ eurjchem-91 4 29     SPACE eurjchem-91 4 30 data datum NOUN eurjchem-91 4 31 . . PUNCT eurjchem-91 4 32     SPACE eurjchem-91 5 1 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 5 2     SPACE eurjchem-91 5 3 quinolinone quinolinone NOUN eurjchem-91 5 4       SPACE eurjchem-91 5 5 chromone chromone NOUN eurjchem-91 5 6     SPACE eurjchem-91 5 7 cyclocondensation cyclocondensation NOUN eurjchem-91 5 8     SPACE eurjchem-91 5 9 knoevenagel knoevenagel NOUN eurjchem-91 5 10     SPACE eurjchem-91 5 11 condensation condensation NOUN eurjchem-91 5 12         SPACE eurjchem-91 5 13 1 1 NUM eurjchem-91 5 14 . . PUNCT eurjchem-91 5 15     SPACE eurjchem-91 5 16 introduction introduction NOUN eurjchem-91 5 17         SPACE eurjchem-91 5 18 4‐hydroxyquinolin‐2(1h)‐ones 4‐hydroxyquinolin‐2(1h)‐one NOUN eurjchem-91 5 19     SPACE eurjchem-91 5 20 represents represent VERB eurjchem-91 5 21     SPACE eurjchem-91 5 22 one one NUM eurjchem-91 5 23     SPACE eurjchem-91 5 24 of of ADP eurjchem-91 5 25     SPACE eurjchem-91 5 26 the the DET eurjchem-91 5 27     SPACE eurjchem-91 5 28 most most ADJ eurjchem-91 5 29     SPACE eurjchem-91 5 30 important important ADJ eurjchem-91 5 31     SPACE eurjchem-91 5 32 class class NOUN eurjchem-91 5 33     SPACE eurjchem-91 5 34 of of ADP eurjchem-91 5 35     SPACE eurjchem-91 5 36 heterocycles heterocycle NOUN eurjchem-91 5 37     SPACE eurjchem-91 5 38 possessing possess VERB eurjchem-91 5 39     SPACE eurjchem-91 5 40 wide wide ADJ eurjchem-91 5 41     SPACE eurjchem-91 5 42 spectrum spectrum NOUN eurjchem-91 5 43     SPACE eurjchem-91 5 44 of of ADP eurjchem-91 5 45     SPACE eurjchem-91 5 46 biological biological ADJ eurjchem-91 5 47     SPACE eurjchem-91 5 48 activities activity NOUN eurjchem-91 5 49     SPACE eurjchem-91 6 1 [ [ X eurjchem-91 6 2 1‐8 1‐8 NOUN eurjchem-91 6 3 ] ] X eurjchem-91 6 4 . . PUNCT eurjchem-91 6 5     SPACE eurjchem-91 6 6 heating heating NOUN eurjchem-91 6 7     SPACE eurjchem-91 6 8 n‐ethylaniline n‐ethylaniline SYM eurjchem-91 6 9     SPACE eurjchem-91 6 10 with with ADP eurjchem-91 6 11     SPACE eurjchem-91 6 12 two two NUM eurjchem-91 6 13     SPACE eurjchem-91 6 14 equivalent equivalent ADJ eurjchem-91 6 15     SPACE eurjchem-91 6 16 diethylmalonate diethylmalonate PROPN eurjchem-91 6 17     SPACE eurjchem-91 6 18 gave give VERB eurjchem-91 6 19     SPACE eurjchem-91 6 20 4‐hydroxypyrano[3,2‐c]‐ 4‐hydroxypyrano[3,2‐c]‐ PROPN eurjchem-91 6 21 quinolin‐2(1h)one quinolin‐2(1h)one NOUN eurjchem-91 6 22     SPACE eurjchem-91 6 23 ( ( PUNCT eurjchem-91 6 24 1 1 NUM eurjchem-91 6 25 ) ) PUNCT eurjchem-91 6 26     SPACE eurjchem-91 6 27 in in ADP eurjchem-91 6 28     SPACE eurjchem-91 6 29 one‐pot one‐pot NOUN eurjchem-91 6 30     SPACE eurjchem-91 6 31 double double ADJ eurjchem-91 6 32     SPACE eurjchem-91 6 33 cyclocondensation cyclocondensation NOUN eurjchem-91 6 34     SPACE eurjchem-91 6 35 process process NOUN eurjchem-91 6 36     SPACE eurjchem-91 7 1 [ [ X eurjchem-91 7 2 9,10 9,10 NUM eurjchem-91 7 3 ] ] X eurjchem-91 7 4 . . PUNCT eurjchem-91 7 5     SPACE eurjchem-91 7 6 the the DET eurjchem-91 7 7     SPACE eurjchem-91 7 8 pyranoquinolinone pyranoquinolinone NOUN eurjchem-91 7 9     SPACE eurjchem-91 7 10 1 1 NUM eurjchem-91 7 11     SPACE eurjchem-91 7 12 is be AUX eurjchem-91 7 13     SPACE eurjchem-91 7 14 a a DET eurjchem-91 7 15     SPACE eurjchem-91 7 16 valuable valuable ADJ eurjchem-91 7 17     SPACE eurjchem-91 7 18 intermediate intermediate ADJ eurjchem-91 7 19     SPACE eurjchem-91 7 20 for for ADP eurjchem-91 7 21     SPACE eurjchem-91 7 22 the the DET eurjchem-91 7 23     SPACE eurjchem-91 7 24 synthesis synthesis NOUN eurjchem-91 7 25     SPACE eurjchem-91 7 26 of of ADP eurjchem-91 7 27     SPACE eurjchem-91 7 28 a a DET eurjchem-91 7 29     SPACE eurjchem-91 7 30 variety variety NOUN eurjchem-91 7 31     SPACE eurjchem-91 7 32 of of ADP eurjchem-91 7 33     SPACE eurjchem-91 7 34 quinolin‐2‐ones quinolin‐2‐one NOUN eurjchem-91 7 35     SPACE eurjchem-91 7 36 bearing bear VERB eurjchem-91 7 37     SPACE eurjchem-91 7 38 various various ADJ eurjchem-91 7 39     SPACE eurjchem-91 7 40 functional functional ADJ eurjchem-91 7 41     SPACE eurjchem-91 7 42 groups group NOUN eurjchem-91 7 43     SPACE eurjchem-91 7 44 in in ADP eurjchem-91 7 45     SPACE eurjchem-91 7 46 position position NOUN eurjchem-91 7 47     SPACE eurjchem-91 7 48 3 3 NUM eurjchem-91 7 49     SPACE eurjchem-91 7 50 via via ADP eurjchem-91 7 51     SPACE eurjchem-91 7 52 chemical chemical NOUN eurjchem-91 7 53     SPACE eurjchem-91 7 54 degradation degradation NOUN eurjchem-91 7 55     SPACE eurjchem-91 7 56 of of ADP eurjchem-91 7 57     SPACE eurjchem-91 7 58 pyrone pyrone NOUN eurjchem-91 7 59     SPACE eurjchem-91 7 60 ring ring NOUN eurjchem-91 7 61     SPACE eurjchem-91 7 62 in in ADP eurjchem-91 7 63     SPACE eurjchem-91 7 64 compound compound NOUN eurjchem-91 7 65     SPACE eurjchem-91 7 66 1 1 NUM eurjchem-91 7 67 . . PUNCT eurjchem-91 7 68     SPACE eurjchem-91 7 69 for for ADP eurjchem-91 7 70     SPACE eurjchem-91 7 71 example example NOUN eurjchem-91 7 72 , , PUNCT eurjchem-91 7 73     SPACE eurjchem-91 7 74 degradation degradation NOUN eurjchem-91 7 75     SPACE eurjchem-91 7 76 of of ADP eurjchem-91 7 77     SPACE eurjchem-91 7 78 1 1 NUM eurjchem-91 7 79     SPACE eurjchem-91 7 80 in in ADP eurjchem-91 7 81     SPACE eurjchem-91 7 82 boiling boil VERB eurjchem-91 7 83     SPACE eurjchem-91 7 84 2n 2n NUM eurjchem-91 7 85     SPACE eurjchem-91 7 86 sodium sodium NOUN eurjchem-91 7 87     SPACE eurjchem-91 7 88 hydroxide hydroxide NOUN eurjchem-91 7 89     SPACE eurjchem-91 7 90 aqueous aqueous ADJ eurjchem-91 7 91     SPACE eurjchem-91 7 92 solution solution NOUN eurjchem-91 7 93     SPACE eurjchem-91 7 94 yielded yield VERB eurjchem-91 7 95     SPACE eurjchem-91 7 96 1‐ethyl‐3‐acetyl‐4‐hydroxyquinolin‐2(1h)‐one 1‐ethyl‐3‐acetyl‐4‐hydroxyquinolin‐2(1h)‐one NUM eurjchem-91 7 97     SPACE eurjchem-91 7 98 through through ADP eurjchem-91 7 99     SPACE eurjchem-91 7 100 pyrone pyrone NOUN eurjchem-91 7 101     SPACE eurjchem-91 7 102 ring ring NOUN eurjchem-91 7 103     SPACE eurjchem-91 7 104 opening opening NOUN eurjchem-91 7 105 , , PUNCT eurjchem-91 7 106     SPACE eurjchem-91 7 107 followed follow VERB eurjchem-91 7 108     SPACE eurjchem-91 7 109 by by ADP eurjchem-91 7 110     SPACE eurjchem-91 7 111 decarboxylation decarboxylation NOUN eurjchem-91 7 112     SPACE eurjchem-91 8 1 [ [ X eurjchem-91 8 2 11,12 11,12 NUM eurjchem-91 8 3 ] ] PUNCT eurjchem-91 8 4 . . PUNCT eurjchem-91 8 5     SPACE eurjchem-91 8 6 in in ADP eurjchem-91 8 7     SPACE eurjchem-91 8 8 continuation continuation NOUN eurjchem-91 8 9     SPACE eurjchem-91 8 10 to to ADP eurjchem-91 8 11     SPACE eurjchem-91 8 12 previous previous ADJ eurjchem-91 8 13     SPACE eurjchem-91 8 14 research research NOUN eurjchem-91 8 15     SPACE eurjchem-91 8 16 on on ADP eurjchem-91 8 17     SPACE eurjchem-91 8 18 4‐ 4‐ PROPN eurjchem-91 8 19 hydroxyquinolin‐2(1h)‐ones hydroxyquinolin‐2(1h)‐one NOUN eurjchem-91 8 20     SPACE eurjchem-91 9 1 [ [ X eurjchem-91 9 2 13‐18 13‐18 X eurjchem-91 9 3 ] ] PUNCT eurjchem-91 9 4 , , PUNCT eurjchem-91 9 5     SPACE eurjchem-91 9 6 the the DET eurjchem-91 9 7     SPACE eurjchem-91 9 8 present present ADJ eurjchem-91 9 9     SPACE eurjchem-91 9 10 paper paper NOUN eurjchem-91 9 11     SPACE eurjchem-91 9 12 reports report VERB eurjchem-91 9 13     SPACE eurjchem-91 9 14 the the DET eurjchem-91 9 15     SPACE eurjchem-91 9 16 synthesis synthesis NOUN eurjchem-91 9 17     SPACE eurjchem-91 9 18 of of ADP eurjchem-91 9 19     SPACE eurjchem-91 9 20 the the DET eurjchem-91 9 21     SPACE eurjchem-91 9 22 new new ADJ eurjchem-91 9 23     SPACE eurjchem-91 9 24 3‐(1‐ethy1‐4‐hydroxy‐2‐oxo‐ 3‐(1‐ethy1‐4‐hydroxy‐2‐oxo‐ NUM eurjchem-91 9 25 2(1h)‐quinolin‐3‐yl)‐3‐oxo‐propanoic 2(1h)‐quinolin‐3‐yl)‐3‐oxo‐propanoic NUM eurjchem-91 9 26     SPACE eurjchem-91 9 27 acid acid NOUN eurjchem-91 9 28     SPACE eurjchem-91 9 29 ( ( PUNCT eurjchem-91 9 30 2 2 NUM eurjchem-91 9 31 ) ) PUNCT eurjchem-91 9 32     SPACE eurjchem-91 9 33 and and CCONJ eurjchem-91 9 34     SPACE eurjchem-91 9 35 the the DET eurjchem-91 9 36     SPACE eurjchem-91 9 37 study study NOUN eurjchem-91 9 38     SPACE eurjchem-91 9 39 of of ADP eurjchem-91 9 40     SPACE eurjchem-91 9 41 its its PRON eurjchem-91 9 42     SPACE eurjchem-91 9 43 chemical chemical NOUN eurjchem-91 9 44     SPACE eurjchem-91 9 45 reactivity reactivity NOUN eurjchem-91 9 46     SPACE eurjchem-91 9 47 towards towards ADP eurjchem-91 9 48     SPACE eurjchem-91 9 49 some some PRON eurjchem-91 9 50     SPACE eurjchem-91 9 51 ortho‐hydroxyaldehydes ortho‐hydroxyaldehyde NOUN eurjchem-91 9 52     SPACE eurjchem-91 9 53 and and CCONJ eurjchem-91 9 54     SPACE eurjchem-91 9 55 ortho‐aminoaldehydes ortho‐aminoaldehyde VERB eurjchem-91 9 56 , , PUNCT eurjchem-91 9 57     SPACE eurjchem-91 9 58 in in ADP eurjchem-91 9 59     SPACE eurjchem-91 9 60 search search NOUN eurjchem-91 9 61     SPACE eurjchem-91 9 62 of of ADP eurjchem-91 9 63     SPACE eurjchem-91 9 64 new new ADJ eurjchem-91 9 65     SPACE eurjchem-91 9 66 quinolinone quinolinone NOUN eurjchem-91 9 67     SPACE eurjchem-91 9 68 derivatives derivative NOUN eurjchem-91 9 69     SPACE eurjchem-91 9 70 of of ADP eurjchem-91 9 71     SPACE eurjchem-91 9 72 potential potential ADJ eurjchem-91 9 73     SPACE eurjchem-91 9 74 biological biological ADJ eurjchem-91 9 75     SPACE eurjchem-91 9 76 activity activity NOUN eurjchem-91 9 77 . . PUNCT eurjchem-91 9 78         SPACE eurjchem-91 10 1 2 2 NUM eurjchem-91 10 2 . . PUNCT eurjchem-91 10 3     SPACE eurjchem-91 10 4 experimental experimental ADJ eurjchem-91 10 5           SPACE eurjchem-91 10 6 2.1 2.1 NUM eurjchem-91 10 7 . . PUNCT eurjchem-91 10 8     SPACE eurjchem-91 10 9 instrumentation instrumentation NOUN eurjchem-91 10 10         SPACE eurjchem-91 10 11 melting melt VERB eurjchem-91 10 12     SPACE eurjchem-91 10 13 points point NOUN eurjchem-91 10 14     SPACE eurjchem-91 10 15 were be AUX eurjchem-91 10 16     SPACE eurjchem-91 10 17 determined determine VERB eurjchem-91 10 18     SPACE eurjchem-91 10 19 on on ADP eurjchem-91 10 20     SPACE eurjchem-91 10 21 a a DET eurjchem-91 10 22     SPACE eurjchem-91 10 23 digital digital ADJ eurjchem-91 10 24     SPACE eurjchem-91 10 25 stuart stuart PROPN eurjchem-91 10 26     SPACE eurjchem-91 10 27 smp3 smp3 PROPN eurjchem-91 10 28     SPACE eurjchem-91 10 29 apparatus apparatus NOUN eurjchem-91 10 30 . . PUNCT eurjchem-91 10 31     SPACE eurjchem-91 11 1 infrared infrare VERB eurjchem-91 11 2     SPACE eurjchem-91 11 3 spectra spectra PROPN eurjchem-91 11 4     SPACE eurjchem-91 11 5 were be AUX eurjchem-91 11 6     SPACE eurjchem-91 11 7 measured measure VERB eurjchem-91 11 8     SPACE eurjchem-91 11 9 on on ADP eurjchem-91 11 10     SPACE eurjchem-91 11 11 a a DET eurjchem-91 11 12     SPACE eurjchem-91 11 13 perkin‐elmer perkin‐elmer NOUN eurjchem-91 11 14     SPACE eurjchem-91 11 15 293 293 NUM eurjchem-91 11 16     SPACE eurjchem-91 11 17 spectrophotometer spectrophotometer NOUN eurjchem-91 11 18     SPACE eurjchem-91 11 19 ( ( PUNCT eurjchem-91 11 20 cm‐1 cm‐1 NOUN eurjchem-91 11 21 ) ) PUNCT eurjchem-91 11 22 , , PUNCT eurjchem-91 11 23     SPACE eurjchem-91 11 24 using use VERB eurjchem-91 11 25     SPACE eurjchem-91 11 26 kbr kbr PROPN eurjchem-91 11 27     SPACE eurjchem-91 11 28 disks disk NOUN eurjchem-91 11 29 . . PUNCT eurjchem-91 11 30     SPACE eurjchem-91 11 31 1h 1h NUM eurjchem-91 11 32     SPACE eurjchem-91 11 33 nmr nmr NOUN eurjchem-91 11 34     SPACE eurjchem-91 11 35 spectra spectra NOUN eurjchem-91 11 36     SPACE eurjchem-91 11 37 were be AUX eurjchem-91 11 38     SPACE eurjchem-91 11 39 measured measure VERB eurjchem-91 11 40     SPACE eurjchem-91 11 41 on on ADP eurjchem-91 11 42     SPACE eurjchem-91 11 43 gemini‐200 gemini‐200 PROPN eurjchem-91 11 44     SPACE eurjchem-91 11 45 ( ( PUNCT eurjchem-91 11 46 200 200 NUM eurjchem-91 11 47     SPACE eurjchem-91 11 48 mhz mhz NOUN eurjchem-91 11 49 ) ) PUNCT eurjchem-91 11 50     SPACE eurjchem-91 11 51 and/or and/or CCONJ eurjchem-91 11 52     SPACE eurjchem-91 11 53 mercury‐300bb mercury‐300bb PROPN eurjchem-91 11 54     SPACE eurjchem-91 11 55 ( ( PUNCT eurjchem-91 11 56 300mhz 300mhz NUM eurjchem-91 11 57 ) ) PUNCT eurjchem-91 11 58     SPACE eurjchem-91 11 59 spectrometers spectrometer NOUN eurjchem-91 11 60 , , PUNCT eurjchem-91 11 61     SPACE eurjchem-91 11 62 using use VERB eurjchem-91 11 63     SPACE eurjchem-91 11 64 dmso‐d6 dmso‐d6 NOUN eurjchem-91 11 65     SPACE eurjchem-91 11 66 as as ADP eurjchem-91 11 67     SPACE eurjchem-91 11 68 solvent solvent NOUN eurjchem-91 11 69     SPACE eurjchem-91 11 70 and and CCONJ eurjchem-91 11 71     SPACE eurjchem-91 11 72 tms tms PROPN eurjchem-91 11 73     SPACE eurjchem-91 11 74 ( ( PUNCT eurjchem-91 11 75 δ δ PROPN eurjchem-91 11 76 ) ) PUNCT eurjchem-91 11 77     SPACE eurjchem-91 11 78 as as ADP eurjchem-91 11 79     SPACE eurjchem-91 11 80 internal internal ADJ eurjchem-91 11 81     SPACE eurjchem-91 11 82 standard standard NOUN eurjchem-91 11 83 . . PUNCT eurjchem-91 11 84     SPACE eurjchem-91 11 85 13c 13c NOUN eurjchem-91 11 86     SPACE eurjchem-91 11 87 nmr nmr NOUN eurjchem-91 11 88     SPACE eurjchem-91 11 89 spectra spectra NOUN eurjchem-91 11 90     SPACE eurjchem-91 11 91 were be AUX eurjchem-91 11 92     SPACE eurjchem-91 11 93 measured measure VERB eurjchem-91 11 94     SPACE eurjchem-91 11 95 on on ADP eurjchem-91 11 96     SPACE eurjchem-91 11 97 a a DET eurjchem-91 11 98     SPACE eurjchem-91 11 99 mercury‐300bb mercury‐300bb NOUN eurjchem-91 11 100     SPACE eurjchem-91 11 101 ( ( PUNCT eurjchem-91 11 102 75mhz 75mhz NOUN eurjchem-91 11 103 ) ) PUNCT eurjchem-91 11 104     SPACE eurjchem-91 11 105 spectrometer spectrometer NOUN eurjchem-91 11 106 , , PUNCT eurjchem-91 11 107     SPACE eurjchem-91 11 108 using use VERB eurjchem-91 11 109     SPACE eurjchem-91 11 110 dmso‐d6 dmso‐d6 NOUN eurjchem-91 11 111     SPACE eurjchem-91 11 112 as as ADP eurjchem-91 11 113     SPACE eurjchem-91 11 114 solvent solvent NOUN eurjchem-91 11 115     SPACE eurjchem-91 11 116 and and CCONJ eurjchem-91 11 117     SPACE eurjchem-91 11 118 tms tms PROPN eurjchem-91 11 119     SPACE eurjchem-91 11 120 ( ( PUNCT eurjchem-91 11 121 δ δ PROPN eurjchem-91 11 122 ) ) PUNCT eurjchem-91 11 123     SPACE eurjchem-91 11 124 as as ADP eurjchem-91 11 125     SPACE eurjchem-91 11 126 internal internal ADJ eurjchem-91 11 127     SPACE eurjchem-91 11 128 standard standard NOUN eurjchem-91 11 129 . . PUNCT eurjchem-91 11 130     SPACE eurjchem-91 11 131 mass mass PROPN eurjchem-91 11 132     SPACE eurjchem-91 11 133 spectra spectra NOUN eurjchem-91 11 134     SPACE eurjchem-91 11 135 were be AUX eurjchem-91 11 136     SPACE eurjchem-91 11 137 obtained obtain VERB eurjchem-91 11 138     SPACE eurjchem-91 11 139 using use VERB eurjchem-91 11 140     SPACE eurjchem-91 11 141 a a DET eurjchem-91 11 142     SPACE eurjchem-91 11 143 gc‐2010 gc‐2010 NOUN eurjchem-91 11 144     SPACE eurjchem-91 11 145 shimadzu shimadzu ADJ eurjchem-91 11 146     SPACE eurjchem-91 11 147 gas gas NOUN eurjchem-91 11 148     SPACE eurjchem-91 11 149 chromatography‐mass chromatography‐mass NOUN eurjchem-91 11 150     SPACE eurjchem-91 11 151 spectrometer spectrometer NOUN eurjchem-91 11 152     SPACE eurjchem-91 11 153 ( ( PUNCT eurjchem-91 11 154 70 70 NUM eurjchem-91 11 155     SPACE eurjchem-91 11 156 ev ev NOUN eurjchem-91 11 157 ) ) PUNCT eurjchem-91 11 158     SPACE eurjchem-91 11 159 instrument instrument NOUN eurjchem-91 11 160 . . PUNCT eurjchem-91 11 161     SPACE eurjchem-91 12 1 elemental elemental ADJ eurjchem-91 12 2     SPACE eurjchem-91 12 3 microanalyses microanalysis NOUN eurjchem-91 12 4     SPACE eurjchem-91 12 5 were be AUX eurjchem-91 12 6     SPACE eurjchem-91 12 7 performed perform VERB eurjchem-91 12 8     SPACE eurjchem-91 12 9 on on ADP eurjchem-91 12 10     SPACE eurjchem-91 12 11 a a DET eurjchem-91 12 12     SPACE eurjchem-91 12 13 perkin perkin NOUN eurjchem-91 12 14 – – PUNCT eurjchem-91 12 15 elmer elmer NOUN eurjchem-91 12 16     SPACE eurjchem-91 12 17 chn‐2400 chn‐2400 PROPN eurjchem-91 12 18     SPACE eurjchem-91 12 19 analyzer analyzer NOUN eurjchem-91 12 20 . . PUNCT eurjchem-91 12 21         SPACE eurjchem-91 12 22 2.2 2.2 NUM eurjchem-91 12 23 . . PUNCT eurjchem-91 12 24     SPACE eurjchem-91 13 1 3­(1­ethy1­4­hydroxy­2­oxo­2(1h)­quinolin­3­yl)­3­ 3­(1­ethy1­4­hydroxy­2­oxo­2(1h)­quinolin­3­yl)­3­ NUM eurjchem-91 13 2 oxopropanoic oxopropanoic ADJ eurjchem-91 13 3     SPACE eurjchem-91 13 4 acid acid NOUN eurjchem-91 13 5     SPACE eurjchem-91 13 6 ( ( PUNCT eurjchem-91 13 7 2 2 NUM eurjchem-91 13 8 ) ) PUNCT eurjchem-91 13 9         SPACE eurjchem-91 13 10 a a DET eurjchem-91 13 11     SPACE eurjchem-91 13 12 solution solution NOUN eurjchem-91 13 13     SPACE eurjchem-91 13 14 of of ADP eurjchem-91 13 15     SPACE eurjchem-91 13 16 6‐ethyl‐4‐hydroxy‐2h‐pyrano[3,2‐c]quino 6‐ethyl‐4‐hydroxy‐2h‐pyrano[3,2‐c]quino NOUN eurjchem-91 13 17     SPACE eurjchem-91 13 18 line‐2,5(6h)‐dione line‐2,5(6h)‐dione NOUN eurjchem-91 13 19     SPACE eurjchem-91 13 20 ( ( PUNCT eurjchem-91 13 21 1 1 NUM eurjchem-91 13 22 ) ) PUNCT eurjchem-91 13 23     SPACE eurjchem-91 13 24 ( ( PUNCT eurjchem-91 13 25 25.7 25.7 NUM eurjchem-91 13 26     SPACE eurjchem-91 13 27 g g NOUN eurjchem-91 13 28 , , PUNCT eurjchem-91 13 29     SPACE eurjchem-91 13 30 100 100 NUM eurjchem-91 13 31     SPACE eurjchem-91 13 32 mmol mmol NOUN eurjchem-91 13 33 ) ) PUNCT eurjchem-91 13 34     SPACE eurjchem-91 13 35 in in ADP eurjchem-91 13 36     SPACE eurjchem-91 13 37 1n 1n NUM eurjchem-91 13 38     SPACE eurjchem-91 13 39 sodium sodium NOUN eurjchem-91 13 40     SPACE eurjchem-91 13 41 hydroxide hydroxide NOUN eurjchem-91 13 42     SPACE eurjchem-91 13 43 aqueous aqueous ADJ eurjchem-91 13 44     SPACE eurjchem-91 13 45 solution solution NOUN eurjchem-91 13 46     SPACE eurjchem-91 13 47 ( ( PUNCT eurjchem-91 13 48 250 250 NUM eurjchem-91 13 49     SPACE eurjchem-91 13 50 ml ml NOUN eurjchem-91 13 51 ) ) PUNCT eurjchem-91 13 52     SPACE eurjchem-91 13 53 was be AUX eurjchem-91 13 54     SPACE eurjchem-91 13 55 warmed warm VERB eurjchem-91 13 56     SPACE eurjchem-91 13 57 at at ADP eurjchem-91 13 58     SPACE eurjchem-91 13 59 40–50 40–50 NOUN eurjchem-91 13 60     SPACE eurjchem-91 13 61 oc oc NOUN eurjchem-91 13 62     SPACE eurjchem-91 13 63 for for ADP eurjchem-91 13 64     SPACE eurjchem-91 13 65 30 30 NUM eurjchem-91 13 66     SPACE eurjchem-91 13 67 min min NOUN eurjchem-91 13 68     SPACE eurjchem-91 13 69 ( ( PUNCT eurjchem-91 13 70 scheme scheme NOUN eurjchem-91 13 71     SPACE eurjchem-91 13 72 1 1 NUM eurjchem-91 13 73 ) ) PUNCT eurjchem-91 13 74 . . PUNCT eurjchem-91 13 75     SPACE eurjchem-91 14 1 the the DET eurjchem-91 14 2     SPACE eurjchem-91 14 3 solution solution NOUN eurjchem-91 14 4     SPACE eurjchem-91 14 5 so so ADV eurjchem-91 14 6     SPACE eurjchem-91 14 7 formed form VERB eurjchem-91 14 8     SPACE eurjchem-91 14 9 was be AUX eurjchem-91 14 10     SPACE eurjchem-91 14 11 filtered filter VERB eurjchem-91 14 12     SPACE eurjchem-91 14 13 and and CCONJ eurjchem-91 14 14     SPACE eurjchem-91 14 15 the the DET eurjchem-91 14 16     SPACE eurjchem-91 14 17 clear clear ADJ eurjchem-91 14 18     SPACE eurjchem-91 14 19 solution solution NOUN eurjchem-91 14 20     SPACE eurjchem-91 14 21 was be AUX eurjchem-91 14 22     SPACE eurjchem-91 14 23 acidified acidify VERB eurjchem-91 14 24     SPACE eurjchem-91 14 25 with with ADP eurjchem-91 14 26     SPACE eurjchem-91 14 27 10 10 NUM eurjchem-91 14 28 % % NOUN eurjchem-91 14 29     SPACE eurjchem-91 14 30 hcl hcl PROPN eurjchem-91 14 31 . . PUNCT eurjchem-91 14 32     SPACE eurjchem-91 15 1 the the DET eurjchem-91 15 2     SPACE eurjchem-91 15 3 precipitate precipitate NOUN eurjchem-91 15 4     SPACE eurjchem-91 15 5 so so ADV eurjchem-91 15 6     SPACE eurjchem-91 15 7 formed form VERB eurjchem-91 15 8     SPACE eurjchem-91 15 9 was be AUX eurjchem-91 15 10     SPACE eurjchem-91 15 11 filtered filter VERB eurjchem-91 15 12 , , PUNCT eurjchem-91 15 13     SPACE eurjchem-91 15 14 washed wash VERB eurjchem-91 15 15     SPACE eurjchem-91 15 16 several several ADJ eurjchem-91 15 17     SPACE eurjchem-91 15 18 times time NOUN eurjchem-91 15 19     SPACE eurjchem-91 15 20 with with ADP eurjchem-91 15 21     SPACE eurjchem-91 15 22 water water NOUN eurjchem-91 15 23 , , PUNCT eurjchem-91 15 24     SPACE eurjchem-91 15 25 air air NOUN eurjchem-91 15 26     SPACE eurjchem-91 15 27 dried dry VERB eurjchem-91 15 28     SPACE eurjchem-91 15 29 and and CCONJ eurjchem-91 15 30     SPACE eurjchem-91 15 31 crystallized crystallize VERB eurjchem-91 15 32     SPACE eurjchem-91 15 33 from from ADP eurjchem-91 15 34     SPACE eurjchem-91 15 35 acetic acetic ADJ eurjchem-91 15 36     SPACE eurjchem-91 15 37 acid acid NOUN eurjchem-91 15 38     SPACE eurjchem-91 15 39 to to PART eurjchem-91 15 40     SPACE eurjchem-91 15 41 give give VERB eurjchem-91 15 42     SPACE eurjchem-91 15 43 2 2 NUM eurjchem-91 15 44     SPACE eurjchem-91 15 45 as as ADP eurjchem-91 15 46     SPACE eurjchem-91 15 47 yellow yellow ADJ eurjchem-91 15 48     SPACE eurjchem-91 15 49 crystals crystal NOUN eurjchem-91 15 50 . . PUNCT eurjchem-91 15 51     SPACE eurjchem-91 16 1 m.p m.p PROPN eurjchem-91 16 2 . . PROPN eurjchem-91 16 3 : : PUNCT eurjchem-91 16 4     SPACE eurjchem-91 16 5 226 226 NUM eurjchem-91 16 6     SPACE eurjchem-91 16 7 oc oc PROPN eurjchem-91 16 8 . . PUNCT eurjchem-91 16 9     SPACE eurjchem-91 16 10 yield yield NOUN eurjchem-91 16 11 : : PUNCT eurjchem-91 16 12     SPACE eurjchem-91 16 13 21 21 NUM eurjchem-91 16 14     SPACE eurjchem-91 16 15 g g NOUN eurjchem-91 16 16 , , PUNCT eurjchem-91 16 17     SPACE eurjchem-91 16 18 76 76 NUM eurjchem-91 16 19 % % NOUN eurjchem-91 16 20 . . PUNCT eurjchem-91 16 21     SPACE eurjchem-91 17 1 ir ir VERB eurjchem-91 17 2     SPACE eurjchem-91 17 3 ( ( PUNCT eurjchem-91 17 4 kbr kbr PROPN eurjchem-91 17 5 , , PUNCT eurjchem-91 17 6     SPACE eurjchem-91 17 7 cm‐1 cm‐1 NOUN eurjchem-91 17 8 ): ): PUNCT eurjchem-91 17 9     SPACE eurjchem-91 17 10 3429 3429 NUM eurjchem-91 17 11     SPACE eurjchem-91 17 12 ( ( PUNCT eurjchem-91 17 13 oh oh INTJ eurjchem-91 17 14 ) ) PUNCT eurjchem-91 17 15 , , PUNCT eurjchem-91 17 16     SPACE eurjchem-91 17 17 3220 3220 NUM eurjchem-91 17 18     SPACE eurjchem-91 17 19 ( ( PUNCT eurjchem-91 17 20 oh oh INTJ eurjchem-91 17 21 ) ) PUNCT eurjchem-91 17 22 , , PUNCT eurjchem-91 17 23     SPACE eurjchem-91 17 24 3074 3074 NUM eurjchem-91 17 25     SPACE eurjchem-91 17 26 ( ( PUNCT eurjchem-91 17 27 charom charom NOUN eurjchem-91 17 28 . . PUNCT eurjchem-91 17 29 ) ) PUNCT eurjchem-91 17 30 , , PUNCT eurjchem-91 17 31     SPACE eurjchem-91 17 32 2978 2978 NUM eurjchem-91 17 33 , , PUNCT eurjchem-91 17 34     SPACE eurjchem-91 17 35 2934 2934 NUM eurjchem-91 17 36 , , PUNCT eurjchem-91 17 37     SPACE eurjchem-91 17 38 2869 2869 NUM eurjchem-91 17 39     SPACE eurjchem-91 17 40 ( ( PUNCT eurjchem-91 17 41 ch3 ch3 PROPN eurjchem-91 17 42 , , PUNCT eurjchem-91 17 43     SPACE eurjchem-91 17 44 ch2 ch2 PROPN eurjchem-91 17 45 ) ) PUNCT eurjchem-91 17 46 , , PUNCT eurjchem-91 17 47     SPACE eurjchem-91 17 48 1727 1727 NUM eurjchem-91 17 49     SPACE eurjchem-91 17 50 ( ( PUNCT eurjchem-91 17 51 c c NOUN eurjchem-91 17 52 = = NOUN eurjchem-91 17 53 ocarboxy ocarboxy ADJ eurjchem-91 17 54 ) ) PUNCT eurjchem-91 17 55 , , PUNCT eurjchem-91 17 56     SPACE eurjchem-91 17 57 1673 1673 NUM eurjchem-91 17 58     SPACE eurjchem-91 17 59 ( ( PUNCT eurjchem-91 17 60 c c NOUN eurjchem-91 17 61 = = NOUN eurjchem-91 17 62 oquinolinone oquinolinone NOUN eurjchem-91 17 63 ) ) PUNCT eurjchem-91 17 64 , , PUNCT eurjchem-91 17 65     SPACE eurjchem-91 17 66 1613 1613 NUM eurjchem-91 17 67     SPACE eurjchem-91 17 68 ( ( PUNCT eurjchem-91 17 69 c c NOUN eurjchem-91 17 70 = = NOUN eurjchem-91 17 71 oketone oketone NOUN eurjchem-91 17 72 ) ) PUNCT eurjchem-91 17 73 . . PUNCT eurjchem-91 17 74     SPACE eurjchem-91 18 1 1h 1h NUM eurjchem-91 18 2     SPACE eurjchem-91 18 3 nmr nmr NOUN eurjchem-91 18 4     SPACE eurjchem-91 18 5 ( ( PUNCT eurjchem-91 18 6 dmso‐d6 dmso‐d6 PROPN eurjchem-91 18 7 , , PUNCT eurjchem-91 18 8     SPACE eurjchem-91 18 9 δ δ PROPN eurjchem-91 18 10 ): ): PUNCT eurjchem-91 18 11     SPACE eurjchem-91 18 12 1.26 1.26 NUM eurjchem-91 18 13     SPACE eurjchem-91 18 14 ( ( PUNCT eurjchem-91 18 15 t t PROPN eurjchem-91 18 16 , , PUNCT eurjchem-91 18 17     SPACE eurjchem-91 18 18 3h 3h NUM eurjchem-91 18 19 , , PUNCT eurjchem-91 18 20     SPACE eurjchem-91 18 21 j=6.8 j=6.8 NOUN eurjchem-91 18 22     SPACE eurjchem-91 18 23 hz hz VERB eurjchem-91 18 24 , , PUNCT eurjchem-91 18 25     SPACE eurjchem-91 18 26 ch2ch3 ch2ch3 ADJ eurjchem-91 18 27 ) ) PUNCT eurjchem-91 18 28 , , PUNCT eurjchem-91 18 29     SPACE eurjchem-91 18 30 4.35 4.35 NUM eurjchem-91 18 31     SPACE eurjchem-91 18 32 ( ( PUNCT eurjchem-91 18 33 q q NOUN eurjchem-91 18 34 , , PUNCT eurjchem-91 18 35     SPACE eurjchem-91 18 36 2h 2h NUM eurjchem-91 18 37 , , PUNCT eurjchem-91 18 38     SPACE eurjchem-91 18 39 j=6.8 j=6.8 NOUN eurjchem-91 18 40     SPACE eurjchem-91 18 41 hz hz VERB eurjchem-91 18 42 , , PUNCT eurjchem-91 18 43     SPACE eurjchem-91 18 44 ch2ch3 ch2ch3 ADJ eurjchem-91 18 45 ) ) PUNCT eurjchem-91 18 46 , , PUNCT eurjchem-91 18 47     SPACE eurjchem-91 18 48 5.56 5.56 NUM eurjchem-91 18 49     SPACE eurjchem-91 18 50 ( ( PUNCT eurjchem-91 18 51 s s PROPN eurjchem-91 18 52 , , PUNCT eurjchem-91 18 53     SPACE eurjchem-91 18 54 2h 2h NUM eurjchem-91 18 55 , , PUNCT eurjchem-91 18 56     SPACE eurjchem-91 18 57 ch2 ch2 NOUN eurjchem-91 18 58 ) ) PUNCT eurjchem-91 18 59 , , PUNCT eurjchem-91 18 60     SPACE eurjchem-91 18 61 7.48 7.48 NUM eurjchem-91 18 62     SPACE eurjchem-91 18 63 ( ( PUNCT eurjchem-91 18 64 d d PROPN eurjchem-91 18 65 , , PUNCT eurjchem-91 18 66     SPACE eurjchem-91 18 67 1h 1h NUM eurjchem-91 18 68 , , PUNCT eurjchem-91 18 69     SPACE eurjchem-91 18 70 j=6.8 j=6.8 NOUN eurjchem-91 18 71     SPACE eurjchem-91 18 72 hz hz VERB eurjchem-91 18 73 , , PUNCT eurjchem-91 18 74     SPACE eurjchem-91 18 75 h‐8 h‐8 NOUN eurjchem-91 18 76 ) ) PUNCT eurjchem-91 18 77 , , PUNCT eurjchem-91 18 78     SPACE eurjchem-91 18 79 7.84 7.84 NUM eurjchem-91 18 80     SPACE eurjchem-91 18 81 ( ( PUNCT eurjchem-91 18 82 m m PROPN eurjchem-91 18 83 , , PUNCT eurjchem-91 18 84     SPACE eurjchem-91 18 85 2h 2h NUM eurjchem-91 18 86 , , PUNCT eurjchem-91 18 87     SPACE eurjchem-91 18 88 h‐6 h‐6 NOUN eurjchem-91 18 89     SPACE eurjchem-91 18 90 and and CCONJ eurjchem-91 18 91     SPACE eurjchem-91 18 92 h‐7 h‐7 NOUN eurjchem-91 18 93 ) ) PUNCT eurjchem-91 18 94 , , PUNCT eurjchem-91 18 95     SPACE eurjchem-91 19 1 8.06 8.06 NUM eurjchem-91 19 2     SPACE eurjchem-91 19 3 ( ( PUNCT eurjchem-91 19 4 d d PROPN eurjchem-91 19 5 , , PUNCT eurjchem-91 19 6     SPACE eurjchem-91 19 7 1h 1h NUM eurjchem-91 19 8 , , PUNCT eurjchem-91 19 9     SPACE eurjchem-91 19 10 j= j= NOUN eurjchem-91 19 11     SPACE eurjchem-91 19 12 8.0 8.0 NUM eurjchem-91 19 13     SPACE eurjchem-91 19 14 hz hz VERB eurjchem-91 19 15 , , PUNCT eurjchem-91 19 16     SPACE eurjchem-91 19 17 h‐5 h‐5 NOUN eurjchem-91 19 18 ) ) PUNCT eurjchem-91 19 19 , , PUNCT eurjchem-91 19 20     SPACE eurjchem-91 19 21 12.02 12.02 NUM eurjchem-91 19 22     SPACE eurjchem-91 19 23 ( ( PUNCT eurjchem-91 19 24 br br PROPN eurjchem-91 19 25 , , PUNCT eurjchem-91 19 26     SPACE eurjchem-91 19 27 1h 1h NUM eurjchem-91 19 28     SPACE eurjchem-91 19 29 exchangeable exchangeable ADJ eurjchem-91 19 30     SPACE eurjchem-91 19 31 with with ADP eurjchem-91 19 32     SPACE eurjchem-91 19 33 d2o d2o NOUN eurjchem-91 19 34 , , PUNCT eurjchem-91 19 35     SPACE eurjchem-91 19 36 ohcarboxy ohcarboxy VERB eurjchem-91 19 37 ) ) PUNCT eurjchem-91 19 38 , , PUNCT eurjchem-91 19 39     SPACE eurjchem-91 19 40 13.41 13.41 NUM eurjchem-91 19 41     SPACE eurjchem-91 19 42 ( ( PUNCT eurjchem-91 19 43 br br PROPN eurjchem-91 19 44 , , PUNCT eurjchem-91 19 45     SPACE eurjchem-91 19 46 1h 1h NUM eurjchem-91 19 47     SPACE eurjchem-91 19 48 exchangeable exchangeable ADJ eurjchem-91 19 49     SPACE eurjchem-91 19 50 with with ADP eurjchem-91 19 51     SPACE eurjchem-91 19 52 d2o d2o NOUN eurjchem-91 19 53 , , PUNCT eurjchem-91 19 54     SPACE eurjchem-91 19 55 ohquinolinone ohquinolinone NOUN eurjchem-91 19 56 ) ) PUNCT eurjchem-91 19 57 . . PUNCT eurjchem-91 19 58     SPACE eurjchem-91 20 1 m m PROPN eurjchem-91 20 2 / / SYM eurjchem-91 20 3 z z NOUN eurjchem-91 20 4     SPACE eurjchem-91 20 5 ( ( PUNCT eurjchem-91 20 6 relative relative ADJ eurjchem-91 20 7     SPACE eurjchem-91 20 8 intensity intensity NOUN eurjchem-91 20 9 ): ): PUNCT eurjchem-91 20 10     SPACE eurjchem-91 20 11 257 257 NUM eurjchem-91 20 12     SPACE eurjchem-91 20 13 ( ( PUNCT eurjchem-91 20 14 m+ m+ NOUN eurjchem-91 20 15     SPACE eurjchem-91 20 16 – – PUNCT eurjchem-91 20 17     SPACE eurjchem-91 20 18 h2o h2o PROPN eurjchem-91 20 19 ) ) PUNCT eurjchem-91 20 20 , , PUNCT eurjchem-91 20 21     SPACE eurjchem-91 20 22 229 229 NUM eurjchem-91 20 23     SPACE eurjchem-91 20 24 ( ( PUNCT eurjchem-91 20 25 100 100 NUM eurjchem-91 20 26 ) ) PUNCT eurjchem-91 20 27 , , PUNCT eurjchem-91 20 28     SPACE eurjchem-91 20 29 214 214 NUM eurjchem-91 20 30     SPACE eurjchem-91 20 31 ( ( PUNCT eurjchem-91 20 32 9 9 NUM eurjchem-91 20 33 ) ) PUNCT eurjchem-91 20 34 , , PUNCT eurjchem-91 20 35     SPACE eurjchem-91 20 36 200 200 NUM eurjchem-91 20 37     SPACE eurjchem-91 20 38 ( ( PUNCT eurjchem-91 20 39 79 79 NUM eurjchem-91 20 40 ) ) PUNCT eurjchem-91 20 41 , , PUNCT eurjchem-91 20 42     SPACE eurjchem-91 20 43 184 184 NUM eurjchem-91 20 44     SPACE eurjchem-91 20 45 ( ( PUNCT eurjchem-91 20 46 11 11 NUM eurjchem-91 20 47 ) ) PUNCT eurjchem-91 20 48 , , PUNCT eurjchem-91 20 49     SPACE eurjchem-91 20 50 158 158 NUM eurjchem-91 20 51     SPACE eurjchem-91 20 52 ( ( PUNCT eurjchem-91 20 53 12 12 NUM eurjchem-91 20 54 ) ) PUNCT eurjchem-91 20 55 , , PUNCT eurjchem-91 20 56     SPACE eurjchem-91 20 57 118 118 NUM eurjchem-91 20 58     SPACE eurjchem-91 20 59 ( ( PUNCT eurjchem-91 20 60 6 6 NUM eurjchem-91 20 61 ) ) PUNCT eurjchem-91 20 62 , , PUNCT eurjchem-91 20 63     SPACE eurjchem-91 20 64 104 104 NUM eurjchem-91 20 65     SPACE eurjchem-91 20 66 ( ( PUNCT eurjchem-91 20 67 4 4 NUM eurjchem-91 20 68 ) ) PUNCT eurjchem-91 20 69 , , PUNCT eurjchem-91 20 70     SPACE eurjchem-91 20 71 77 77 NUM eurjchem-91 20 72     SPACE eurjchem-91 20 73 ( ( PUNCT eurjchem-91 20 74 3 3 NUM eurjchem-91 20 75 ) ) PUNCT eurjchem-91 20 76 . . PUNCT eurjchem-91 20 77     SPACE eurjchem-91 21 1 anal anal ADJ eurjchem-91 21 2 . . PUNCT eurjchem-91 21 3     SPACE eurjchem-91 21 4 calcd calcd NOUN eurjchem-91 21 5     SPACE eurjchem-91 21 6 for for ADP eurjchem-91 21 7     SPACE eurjchem-91 21 8 c14h13no5 c14h13no5 NOUN eurjchem-91 21 9     SPACE eurjchem-91 21 10 ( ( PUNCT eurjchem-91 21 11 275.26 275.26 NUM eurjchem-91 21 12 ): ): PUNCT eurjchem-91 21 13     SPACE eurjchem-91 21 14 c c NOUN eurjchem-91 21 15 , , PUNCT eurjchem-91 21 16     SPACE eurjchem-91 21 17 61.06 61.06 NUM eurjchem-91 21 18 ; ; PUNCT eurjchem-91 21 19     SPACE eurjchem-91 21 20 h h NOUN eurjchem-91 21 21 , , PUNCT eurjchem-91 21 22     SPACE eurjchem-91 21 23 4.76 4.76 NUM eurjchem-91 21 24 ; ; PUNCT eurjchem-91 21 25     SPACE eurjchem-91 21 26 n n CCONJ eurjchem-91 21 27 , , PUNCT eurjchem-91 21 28     SPACE eurjchem-91 21 29 5.09 5.09 NUM eurjchem-91 21 30 % % NOUN eurjchem-91 21 31 . . PUNCT eurjchem-91 21 32     SPACE eurjchem-91 21 33 found find VERB eurjchem-91 21 34     SPACE eurjchem-91 21 35 c c NOUN eurjchem-91 21 36 , , PUNCT eurjchem-91 21 37     SPACE eurjchem-91 21 38 61.31 61.31 NUM eurjchem-91 21 39 ; ; PUNCT eurjchem-91 21 40     SPACE eurjchem-91 21 41 h h NOUN eurjchem-91 21 42 , , PUNCT eurjchem-91 21 43     SPACE eurjchem-91 21 44 4.99 4.99 NUM eurjchem-91 21 45 ; ; PUNCT eurjchem-91 21 46     SPACE eurjchem-91 21 47 n n CCONJ eurjchem-91 21 48 , , PUNCT eurjchem-91 21 49     SPACE eurjchem-91 21 50 5.31 5.31 NUM eurjchem-91 21 51 % % NOUN eurjchem-91 21 52 . . PUNCT eurjchem-91 21 53         SPACE eurjchem-91 21 54 2.3 2.3 NUM eurjchem-91 21 55 . . PUNCT eurjchem-91 21 56     SPACE eurjchem-91 22 1 2­[(1­ethyl­4­hydroxy­2­oxo­1,2­dihydro­quinolin­3­ 2­[(1­ethyl­4­hydroxy­2­oxo­1,2­dihydro­quinolin­3­ PROPN eurjchem-91 22 2 yl)carbonyl)]­3­(2­hydroxy yl)carbonyl)]­3­(2­hydroxy PROPN eurjchem-91 22 3       SPACE eurjchem-91 22 4 phenyl)­prop­2­enoic phenyl)­prop­2­enoic ADV eurjchem-91 22 5     SPACE eurjchem-91 22 6 acid acid NOUN eurjchem-91 22 7     SPACE eurjchem-91 22 8 ( ( PUNCT eurjchem-91 22 9 3 3 NUM eurjchem-91 22 10 ) ) PUNCT eurjchem-91 22 11         SPACE eurjchem-91 22 12 a a DET eurjchem-91 22 13     SPACE eurjchem-91 22 14 mixture mixture NOUN eurjchem-91 22 15     SPACE eurjchem-91 22 16 of of ADP eurjchem-91 22 17     SPACE eurjchem-91 22 18 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 22 19     SPACE eurjchem-91 22 20 2 2 NUM eurjchem-91 22 21     SPACE eurjchem-91 22 22 ( ( PUNCT eurjchem-91 22 23 0.55 0.55 NUM eurjchem-91 22 24     SPACE eurjchem-91 22 25 g g NOUN eurjchem-91 22 26 , , PUNCT eurjchem-91 22 27     SPACE eurjchem-91 22 28 2 2 NUM eurjchem-91 22 29     SPACE eurjchem-91 22 30 mmol mmol NOUN eurjchem-91 22 31 ) ) PUNCT eurjchem-91 22 32     SPACE eurjchem-91 22 33 and and CCONJ eurjchem-91 22 34     SPACE eurjchem-91 22 35 salicylaldehyde salicylaldehyde NOUN eurjchem-91 22 36     SPACE eurjchem-91 22 37 ( ( PUNCT eurjchem-91 22 38 0.21 0.21 NUM eurjchem-91 22 39     SPACE eurjchem-91 22 40 ml ml NOUN eurjchem-91 22 41 , , PUNCT eurjchem-91 22 42     SPACE eurjchem-91 22 43 2 2 NUM eurjchem-91 22 44     SPACE eurjchem-91 22 45 mmol mmol NOUN eurjchem-91 22 46 ) ) PUNCT eurjchem-91 22 47 , , PUNCT eurjchem-91 22 48     SPACE eurjchem-91 22 49 in in ADP eurjchem-91 22 50     SPACE eurjchem-91 22 51 glacial glacial ADJ eurjchem-91 22 52     SPACE eurjchem-91 22 53 acetic acetic ADJ eurjchem-91 22 54     SPACE eurjchem-91 22 55 acid acid NOUN eurjchem-91 22 56     SPACE eurjchem-91 22 57 ( ( PUNCT eurjchem-91 22 58 10 10 NUM eurjchem-91 22 59     SPACE eurjchem-91 22 60 196 196 NUM eurjchem-91 22 61     SPACE eurjchem-91 22 62 ibrahim ibrahim PROPN eurjchem-91 22 63     SPACE eurjchem-91 22 64 et et PROPN eurjchem-91 22 65     SPACE eurjchem-91 22 66 al al PROPN eurjchem-91 22 67 . . PROPN eurjchem-91 22 68     SPACE eurjchem-91 22 69 / / SYM eurjchem-91 22 70     SPACE eurjchem-91 22 71 european european ADJ eurjchem-91 22 72     SPACE eurjchem-91 22 73 journal journal NOUN eurjchem-91 22 74     SPACE eurjchem-91 22 75 of of ADP eurjchem-91 22 76     SPACE eurjchem-91 22 77 chemistry chemistry NOUN eurjchem-91 22 78     SPACE eurjchem-91 22 79 1 1 NUM eurjchem-91 22 80     SPACE eurjchem-91 22 81 ( ( PUNCT eurjchem-91 22 82 3 3 NUM eurjchem-91 22 83 ) ) PUNCT eurjchem-91 22 84     SPACE eurjchem-91 22 85 ( ( PUNCT eurjchem-91 22 86 2010 2010 NUM eurjchem-91 22 87 ) ) PUNCT eurjchem-91 22 88     SPACE eurjchem-91 22 89 195­199 195­199 NUM eurjchem-91 22 90         SPACE eurjchem-91 22 91 ml ml NOUN eurjchem-91 22 92 ) ) PUNCT eurjchem-91 22 93     SPACE eurjchem-91 22 94 and and CCONJ eurjchem-91 22 95     SPACE eurjchem-91 22 96 freshly freshly ADV eurjchem-91 22 97     SPACE eurjchem-91 22 98 fused fuse VERB eurjchem-91 22 99     SPACE eurjchem-91 22 100 sodium sodium NOUN eurjchem-91 22 101     SPACE eurjchem-91 22 102 acetate acetate NOUN eurjchem-91 22 103     SPACE eurjchem-91 22 104 ( ( PUNCT eurjchem-91 22 105 0.2 0.2 NUM eurjchem-91 22 106     SPACE eurjchem-91 22 107 g g NOUN eurjchem-91 22 108 ) ) PUNCT eurjchem-91 22 109 , , PUNCT eurjchem-91 22 110     SPACE eurjchem-91 22 111 was be AUX eurjchem-91 22 112     SPACE eurjchem-91 22 113 heated heated ADJ eurjchem-91 22 114     SPACE eurjchem-91 22 115 at at ADP eurjchem-91 22 116     SPACE eurjchem-91 22 117 reflux reflux NOUN eurjchem-91 22 118     SPACE eurjchem-91 22 119 for for ADP eurjchem-91 22 120     SPACE eurjchem-91 22 121 3h 3h NUM eurjchem-91 22 122     SPACE eurjchem-91 22 123 ( ( PUNCT eurjchem-91 22 124 scheme scheme NOUN eurjchem-91 22 125     SPACE eurjchem-91 22 126 2 2 NUM eurjchem-91 22 127 ) ) PUNCT eurjchem-91 22 128 . . PUNCT eurjchem-91 22 129     SPACE eurjchem-91 23 1 the the DET eurjchem-91 23 2     SPACE eurjchem-91 23 3 yellow yellow ADJ eurjchem-91 23 4     SPACE eurjchem-91 23 5 crystals crystal NOUN eurjchem-91 23 6     SPACE eurjchem-91 23 7 obtained obtain VERB eurjchem-91 23 8     SPACE eurjchem-91 23 9 after after SCONJ eurjchem-91 23 10     SPACE eurjchem-91 23 11 cooling cooling NOUN eurjchem-91 23 12     SPACE eurjchem-91 23 13 were be AUX eurjchem-91 23 14     SPACE eurjchem-91 23 15 filtered filter VERB eurjchem-91 23 16     SPACE eurjchem-91 23 17 and and CCONJ eurjchem-91 23 18     SPACE eurjchem-91 23 19 recrystallized recrystallize VERB eurjchem-91 23 20     SPACE eurjchem-91 23 21 from from ADP eurjchem-91 23 22     SPACE eurjchem-91 23 23 acetic acetic ADJ eurjchem-91 23 24     SPACE eurjchem-91 23 25 acid acid NOUN eurjchem-91 23 26     SPACE eurjchem-91 23 27 to to PART eurjchem-91 23 28     SPACE eurjchem-91 23 29 give give VERB eurjchem-91 23 30     SPACE eurjchem-91 23 31 3 3 NUM eurjchem-91 23 32     SPACE eurjchem-91 23 33 as as ADV eurjchem-91 23 34     SPACE eurjchem-91 23 35 yellow yellow ADJ eurjchem-91 23 36     SPACE eurjchem-91 23 37 crystals crystal NOUN eurjchem-91 23 38 . . PUNCT eurjchem-91 23 39     SPACE eurjchem-91 24 1 m.p m.p PROPN eurjchem-91 24 2 . . PROPN eurjchem-91 24 3 : : PUNCT eurjchem-91 24 4     SPACE eurjchem-91 24 5 256 256 NUM eurjchem-91 24 6     SPACE eurjchem-91 24 7 oc oc PROPN eurjchem-91 24 8 . . PUNCT eurjchem-91 24 9     SPACE eurjchem-91 24 10 yield yield NOUN eurjchem-91 24 11 : : PUNCT eurjchem-91 24 12     SPACE eurjchem-91 24 13 0.37 0.37 NUM eurjchem-91 24 14     SPACE eurjchem-91 24 15 g g NOUN eurjchem-91 24 16 , , PUNCT eurjchem-91 24 17     SPACE eurjchem-91 24 18 49 49 NUM eurjchem-91 24 19 % % NOUN eurjchem-91 24 20 . . PUNCT eurjchem-91 24 21     SPACE eurjchem-91 25 1 ir ir VERB eurjchem-91 25 2     SPACE eurjchem-91 25 3 ( ( PUNCT eurjchem-91 25 4 kbr kbr PROPN eurjchem-91 25 5 , , PUNCT eurjchem-91 25 6     SPACE eurjchem-91 25 7 cm‐1 cm‐1 NOUN eurjchem-91 25 8 ): ): PUNCT eurjchem-91 25 9     SPACE eurjchem-91 25 10 3429 3429 NUM eurjchem-91 25 11     SPACE eurjchem-91 25 12 ( ( PUNCT eurjchem-91 25 13 oh oh INTJ eurjchem-91 25 14 ) ) PUNCT eurjchem-91 25 15 , , PUNCT eurjchem-91 25 16     SPACE eurjchem-91 25 17 3045 3045 NUM eurjchem-91 25 18     SPACE eurjchem-91 25 19 ( ( PUNCT eurjchem-91 25 20 charom charom NOUN eurjchem-91 25 21 . . PUNCT eurjchem-91 25 22 ) ) PUNCT eurjchem-91 25 23 , , PUNCT eurjchem-91 25 24     SPACE eurjchem-91 25 25 2975 2975 NUM eurjchem-91 25 26 , , PUNCT eurjchem-91 25 27     SPACE eurjchem-91 25 28 2890 2890 NUM eurjchem-91 25 29     SPACE eurjchem-91 25 30 ( ( PUNCT eurjchem-91 25 31 ch3 ch3 PROPN eurjchem-91 25 32 , , PUNCT eurjchem-91 25 33     SPACE eurjchem-91 25 34 ch2 ch2 PROPN eurjchem-91 25 35 ) ) PUNCT eurjchem-91 25 36 , , PUNCT eurjchem-91 25 37     SPACE eurjchem-91 25 38 1724 1724 NUM eurjchem-91 25 39     SPACE eurjchem-91 25 40 ( ( PUNCT eurjchem-91 25 41 c c NOUN eurjchem-91 25 42 = = NOUN eurjchem-91 25 43 ocarboxy ocarboxy ADJ eurjchem-91 25 44 ) ) PUNCT eurjchem-91 25 45 , , PUNCT eurjchem-91 25 46     SPACE eurjchem-91 25 47 1642 1642 NUM eurjchem-91 25 48     SPACE eurjchem-91 25 49 ( ( PUNCT eurjchem-91 25 50 c c NOUN eurjchem-91 25 51 = = NOUN eurjchem-91 25 52 oquinolinone oquinolinone NOUN eurjchem-91 25 53 ) ) PUNCT eurjchem-91 25 54 , , PUNCT eurjchem-91 25 55     SPACE eurjchem-91 25 56 1603 1603 NUM eurjchem-91 25 57     SPACE eurjchem-91 25 58 ( ( PUNCT eurjchem-91 25 59 c c NOUN eurjchem-91 25 60 = = NOUN eurjchem-91 25 61 oketone oketone NOUN eurjchem-91 25 62 ) ) PUNCT eurjchem-91 25 63 . . PUNCT eurjchem-91 25 64     SPACE eurjchem-91 25 65 1h 1h NUM eurjchem-91 25 66     SPACE eurjchem-91 25 67 nmr nmr NOUN eurjchem-91 25 68     SPACE eurjchem-91 25 69 ( ( PUNCT eurjchem-91 25 70 dmso‐d6 dmso‐d6 PROPN eurjchem-91 25 71 , , PUNCT eurjchem-91 25 72     SPACE eurjchem-91 25 73 δ δ PROPN eurjchem-91 25 74 ): ): PUNCT eurjchem-91 25 75     SPACE eurjchem-91 25 76 1.14 1.14 NUM eurjchem-91 25 77     SPACE eurjchem-91 25 78 ( ( PUNCT eurjchem-91 25 79 t t PROPN eurjchem-91 25 80 , , PUNCT eurjchem-91 25 81     SPACE eurjchem-91 25 82 3h 3h NUM eurjchem-91 25 83 , , PUNCT eurjchem-91 25 84     SPACE eurjchem-91 25 85 j=6.8 j=6.8 NOUN eurjchem-91 25 86     SPACE eurjchem-91 25 87 hz hz VERB eurjchem-91 25 88 , , PUNCT eurjchem-91 25 89     SPACE eurjchem-91 25 90 ch3 ch3 PROPN eurjchem-91 25 91 ) ) PUNCT eurjchem-91 25 92 , , PUNCT eurjchem-91 25 93     SPACE eurjchem-91 25 94 4.17 4.17 NUM eurjchem-91 25 95     SPACE eurjchem-91 25 96 ( ( PUNCT eurjchem-91 25 97 q q NOUN eurjchem-91 25 98 , , PUNCT eurjchem-91 25 99     SPACE eurjchem-91 25 100 2h 2h NUM eurjchem-91 25 101 , , PUNCT eurjchem-91 25 102     SPACE eurjchem-91 25 103 j=6.8 j=6.8 NOUN eurjchem-91 25 104     SPACE eurjchem-91 25 105 hz hz VERB eurjchem-91 25 106 , , PUNCT eurjchem-91 25 107     SPACE eurjchem-91 25 108 ch2 ch2 NOUN eurjchem-91 25 109 ) ) PUNCT eurjchem-91 25 110 , , PUNCT eurjchem-91 25 111     SPACE eurjchem-91 25 112 5.70 5.70 NUM eurjchem-91 25 113     SPACE eurjchem-91 25 114 ( ( PUNCT eurjchem-91 25 115 s s PROPN eurjchem-91 25 116 , , PUNCT eurjchem-91 25 117     SPACE eurjchem-91 25 118 1h 1h NUM eurjchem-91 25 119 , , PUNCT eurjchem-91 25 120     SPACE eurjchem-91 25 121 chmethine chmethine NOUN eurjchem-91 25 122 ) ) PUNCT eurjchem-91 25 123 , , PUNCT eurjchem-91 25 124     SPACE eurjchem-91 25 125 7.36–7.88 7.36–7.88 NUM eurjchem-91 25 126     SPACE eurjchem-91 25 127 ( ( PUNCT eurjchem-91 25 128 m m PROPN eurjchem-91 25 129 , , PUNCT eurjchem-91 25 130     SPACE eurjchem-91 25 131 6h 6h NOUN eurjchem-91 25 132 , , PUNCT eurjchem-91 25 133     SPACE eurjchem-91 25 134 ar‐h ar‐h NOUN eurjchem-91 25 135 ) ) PUNCT eurjchem-91 25 136 , , PUNCT eurjchem-91 25 137     SPACE eurjchem-91 25 138 8.15‐8.18 8.15‐8.18 NUM eurjchem-91 25 139     SPACE eurjchem-91 25 140 ( ( PUNCT eurjchem-91 25 141 m m PROPN eurjchem-91 25 142 , , PUNCT eurjchem-91 25 143     SPACE eurjchem-91 25 144 2h 2h NUM eurjchem-91 25 145 , , PUNCT eurjchem-91 25 146     SPACE eurjchem-91 25 147 ar‐h ar‐h NOUN eurjchem-91 25 148 ) ) PUNCT eurjchem-91 25 149 , , PUNCT eurjchem-91 25 150     SPACE eurjchem-91 25 151 11.72 11.72 NUM eurjchem-91 25 152     SPACE eurjchem-91 25 153 ( ( PUNCT eurjchem-91 25 154 br br PROPN eurjchem-91 25 155 , , PUNCT eurjchem-91 25 156     SPACE eurjchem-91 25 157 1h 1h NUM eurjchem-91 25 158     SPACE eurjchem-91 25 159 exchangeable exchangeable ADJ eurjchem-91 25 160     SPACE eurjchem-91 25 161 with with ADP eurjchem-91 25 162     SPACE eurjchem-91 25 163 d2o d2o NOUN eurjchem-91 25 164 , , PUNCT eurjchem-91 25 165     SPACE eurjchem-91 25 166 ohsalicylaldehyde ohsalicylaldehyde NOUN eurjchem-91 25 167 ) ) PUNCT eurjchem-91 25 168 , , PUNCT eurjchem-91 25 169     SPACE eurjchem-91 25 170 14.69 14.69 NUM eurjchem-91 25 171     SPACE eurjchem-91 25 172 ( ( PUNCT eurjchem-91 25 173 br br PROPN eurjchem-91 25 174 , , PUNCT eurjchem-91 25 175     SPACE eurjchem-91 25 176 2h 2h NUM eurjchem-91 25 177     SPACE eurjchem-91 25 178 exchangeable exchangeable ADJ eurjchem-91 25 179     SPACE eurjchem-91 25 180 with with ADP eurjchem-91 25 181     SPACE eurjchem-91 25 182 d2o d2o NOUN eurjchem-91 25 183 , , PUNCT eurjchem-91 25 184     SPACE eurjchem-91 25 185 ohquinoline ohquinoline NOUN eurjchem-91 25 186     SPACE eurjchem-91 25 187 and and CCONJ eurjchem-91 25 188     SPACE eurjchem-91 25 189 ohcarboxy ohcarboxy NOUN eurjchem-91 25 190 ) ) PUNCT eurjchem-91 25 191 . . PUNCT eurjchem-91 25 192     SPACE eurjchem-91 26 1 anal anal ADJ eurjchem-91 26 2 . . PUNCT eurjchem-91 26 3     SPACE eurjchem-91 26 4 calcd calcd NOUN eurjchem-91 26 5     SPACE eurjchem-91 26 6 for for ADP eurjchem-91 26 7     SPACE eurjchem-91 26 8 c21h17no6 c21h17no6 NOUN eurjchem-91 26 9     SPACE eurjchem-91 26 10 ( ( PUNCT eurjchem-91 26 11 379.36 379.36 NUM eurjchem-91 26 12 ): ): PUNCT eurjchem-91 26 13     SPACE eurjchem-91 26 14 c c NOUN eurjchem-91 26 15 , , PUNCT eurjchem-91 26 16     SPACE eurjchem-91 26 17 66.49 66.49 NUM eurjchem-91 26 18 ; ; PUNCT eurjchem-91 26 19     SPACE eurjchem-91 26 20 h h NOUN eurjchem-91 26 21 , , PUNCT eurjchem-91 26 22     SPACE eurjchem-91 26 23 4.52 4.52 NUM eurjchem-91 26 24 ; ; PUNCT eurjchem-91 26 25     SPACE eurjchem-91 26 26 n n CCONJ eurjchem-91 26 27 , , PUNCT eurjchem-91 26 28     SPACE eurjchem-91 26 29 3.69 3.69 NUM eurjchem-91 26 30 % % NOUN eurjchem-91 26 31 . . PUNCT eurjchem-91 26 32     SPACE eurjchem-91 26 33 found find VERB eurjchem-91 26 34 : : PUNCT eurjchem-91 26 35     SPACE eurjchem-91 26 36 c c X eurjchem-91 26 37 , , PUNCT eurjchem-91 26 38     SPACE eurjchem-91 26 39 66.42 66.42 NUM eurjchem-91 26 40 ; ; PUNCT eurjchem-91 26 41     SPACE eurjchem-91 26 42 h h NOUN eurjchem-91 26 43 , , PUNCT eurjchem-91 26 44     SPACE eurjchem-91 26 45 4.36 4.36 NUM eurjchem-91 26 46 ; ; PUNCT eurjchem-91 26 47     SPACE eurjchem-91 26 48 n n CCONJ eurjchem-91 26 49 , , PUNCT eurjchem-91 26 50     SPACE eurjchem-91 26 51 3.46 3.46 NUM eurjchem-91 26 52 % % NOUN eurjchem-91 26 53 . . PUNCT eurjchem-91 26 54         SPACE eurjchem-91 26 55 scheme scheme NOUN eurjchem-91 26 56     SPACE eurjchem-91 26 57 1 1 NUM eurjchem-91 26 58             SPACE eurjchem-91 26 59 scheme scheme NOUN eurjchem-91 26 60     SPACE eurjchem-91 26 61 2 2 NUM eurjchem-91 26 62         SPACE eurjchem-91 26 63 2.4 2.4 NUM eurjchem-91 26 64 . . PUNCT eurjchem-91 26 65     SPACE eurjchem-91 27 1 6­ethyl­3­(2­hydroxybenzylidene)­2h­pyrano[3,2­ 6­ethyl­3­(2­hydroxybenzylidene)­2h­pyrano[3,2­ NUM eurjchem-91 27 2 c]quinoline­2,4,5(3h,6h c]quinoline­2,4,5(3h,6h NOUN eurjchem-91 27 3 ) ) PUNCT eurjchem-91 27 4     SPACE eurjchem-91 27 5 trione trione NOUN eurjchem-91 27 6     SPACE eurjchem-91 27 7 ( ( PUNCT eurjchem-91 27 8 4 4 NUM eurjchem-91 27 9 ) ) PUNCT eurjchem-91 27 10         SPACE eurjchem-91 27 11 2.4.1 2.4.1 NUM eurjchem-91 27 12 . . PUNCT eurjchem-91 27 13     SPACE eurjchem-91 27 14 method method VERB eurjchem-91 27 15     SPACE eurjchem-91 27 16 a a DET eurjchem-91 27 17         SPACE eurjchem-91 27 18 compound compound NOUN eurjchem-91 27 19     SPACE eurjchem-91 27 20 3 3 NUM eurjchem-91 27 21     SPACE eurjchem-91 27 22 ( ( PUNCT eurjchem-91 27 23 0.379 0.379 NUM eurjchem-91 27 24     SPACE eurjchem-91 27 25 g g NOUN eurjchem-91 27 26 , , PUNCT eurjchem-91 27 27     SPACE eurjchem-91 27 28 1 1 NUM eurjchem-91 27 29     SPACE eurjchem-91 27 30 mmol mmol NOUN eurjchem-91 27 31 ) ) PUNCT eurjchem-91 27 32     SPACE eurjchem-91 27 33 in in ADP eurjchem-91 27 34     SPACE eurjchem-91 27 35 concentrated concentrate VERB eurjchem-91 27 36     SPACE eurjchem-91 27 37 h2so4 h2so4 PROPN eurjchem-91 27 38     SPACE eurjchem-91 27 39 ( ( PUNCT eurjchem-91 27 40 5 5 NUM eurjchem-91 27 41     SPACE eurjchem-91 27 42 ml ml NOUN eurjchem-91 27 43 ) ) PUNCT eurjchem-91 27 44     SPACE eurjchem-91 27 45 was be AUX eurjchem-91 27 46     SPACE eurjchem-91 27 47 heated heated ADJ eurjchem-91 27 48     SPACE eurjchem-91 27 49 on on ADP eurjchem-91 27 50     SPACE eurjchem-91 27 51 a a DET eurjchem-91 27 52     SPACE eurjchem-91 27 53 water water NOUN eurjchem-91 27 54     SPACE eurjchem-91 27 55 bath bath NOUN eurjchem-91 27 56     SPACE eurjchem-91 27 57 for for ADP eurjchem-91 27 58     SPACE eurjchem-91 27 59 2h 2h NUM eurjchem-91 27 60 . . PUNCT eurjchem-91 27 61     SPACE eurjchem-91 27 62 after after ADP eurjchem-91 27 63     SPACE eurjchem-91 27 64 cooling cooling NOUN eurjchem-91 27 65 , , PUNCT eurjchem-91 27 66     SPACE eurjchem-91 27 67 the the DET eurjchem-91 27 68     SPACE eurjchem-91 27 69 reaction reaction NOUN eurjchem-91 27 70     SPACE eurjchem-91 27 71 mixture mixture NOUN eurjchem-91 27 72     SPACE eurjchem-91 27 73 was be AUX eurjchem-91 27 74     SPACE eurjchem-91 27 75 poured pour VERB eurjchem-91 27 76     SPACE eurjchem-91 27 77 onto onto ADP eurjchem-91 27 78     SPACE eurjchem-91 27 79 ice ice NOUN eurjchem-91 27 80 / / SYM eurjchem-91 27 81 water water NOUN eurjchem-91 27 82 , , PUNCT eurjchem-91 27 83     SPACE eurjchem-91 27 84 the the DET eurjchem-91 27 85     SPACE eurjchem-91 27 86 precipitate precipitate NOUN eurjchem-91 27 87     SPACE eurjchem-91 27 88 so so ADV eurjchem-91 27 89     SPACE eurjchem-91 27 90 formed form VERB eurjchem-91 27 91     SPACE eurjchem-91 27 92 was be AUX eurjchem-91 27 93     SPACE eurjchem-91 27 94 filtered filter VERB eurjchem-91 27 95 , , PUNCT eurjchem-91 27 96     SPACE eurjchem-91 27 97 washed wash VERB eurjchem-91 27 98     SPACE eurjchem-91 27 99 several several ADJ eurjchem-91 27 100     SPACE eurjchem-91 27 101 times time NOUN eurjchem-91 27 102     SPACE eurjchem-91 27 103 with with ADP eurjchem-91 27 104     SPACE eurjchem-91 27 105 h2o h2o NOUN eurjchem-91 27 106     SPACE eurjchem-91 27 107 and and CCONJ eurjchem-91 27 108     SPACE eurjchem-91 27 109 crystallized crystallize VERB eurjchem-91 27 110     SPACE eurjchem-91 27 111 from from ADP eurjchem-91 27 112     SPACE eurjchem-91 27 113 dmf dmf PROPN eurjchem-91 27 114     SPACE eurjchem-91 27 115 to to PART eurjchem-91 27 116     SPACE eurjchem-91 27 117 give give VERB eurjchem-91 27 118     SPACE eurjchem-91 27 119 4 4 NUM eurjchem-91 27 120     SPACE eurjchem-91 27 121 as as ADP eurjchem-91 27 122     SPACE eurjchem-91 27 123 yellow yellow ADJ eurjchem-91 27 124     SPACE eurjchem-91 27 125 crystals crystal NOUN eurjchem-91 27 126 . . PUNCT eurjchem-91 27 127     SPACE eurjchem-91 28 1 m.p m.p PROPN eurjchem-91 28 2 . . PROPN eurjchem-91 28 3 : : PUNCT eurjchem-91 28 4     SPACE eurjchem-91 28 5 240‐ 240‐ NUM eurjchem-91 28 6 241 241 NUM eurjchem-91 28 7     SPACE eurjchem-91 28 8 ºc ºc PROPN eurjchem-91 28 9 . . PUNCT eurjchem-91 28 10     SPACE eurjchem-91 28 11 yield yield NOUN eurjchem-91 28 12 : : PUNCT eurjchem-91 28 13     SPACE eurjchem-91 28 14 0.23 0.23 NUM eurjchem-91 28 15     SPACE eurjchem-91 28 16 g g NOUN eurjchem-91 28 17 , , PUNCT eurjchem-91 28 18     SPACE eurjchem-91 28 19 64 64 NUM eurjchem-91 28 20 % % NOUN eurjchem-91 28 21     SPACE eurjchem-91 28 22 ( ( PUNCT eurjchem-91 28 23 scheme scheme NOUN eurjchem-91 28 24     SPACE eurjchem-91 28 25 2 2 NUM eurjchem-91 28 26 ) ) PUNCT eurjchem-91 28 27 . . PUNCT eurjchem-91 28 28         SPACE eurjchem-91 29 1 2.4.2 2.4.2 NUM eurjchem-91 29 2 . . PUNCT eurjchem-91 29 3     SPACE eurjchem-91 29 4 method method VERB eurjchem-91 29 5     SPACE eurjchem-91 29 6 b b NOUN eurjchem-91 29 7         SPACE eurjchem-91 29 8 a a DET eurjchem-91 29 9     SPACE eurjchem-91 29 10 mixture mixture NOUN eurjchem-91 29 11     SPACE eurjchem-91 29 12 of of ADP eurjchem-91 29 13     SPACE eurjchem-91 29 14 compound compound NOUN eurjchem-91 29 15     SPACE eurjchem-91 29 16 1 1 NUM eurjchem-91 29 17     SPACE eurjchem-91 29 18 ( ( PUNCT eurjchem-91 29 19 0.514 0.514 NUM eurjchem-91 29 20     SPACE eurjchem-91 29 21 g g NOUN eurjchem-91 29 22 , , PUNCT eurjchem-91 29 23     SPACE eurjchem-91 29 24 2 2 NUM eurjchem-91 29 25     SPACE eurjchem-91 29 26 mmol mmol NOUN eurjchem-91 29 27 ) ) PUNCT eurjchem-91 29 28     SPACE eurjchem-91 29 29 and and CCONJ eurjchem-91 29 30     SPACE eurjchem-91 29 31 salicylaldehyde salicylaldehyde NOUN eurjchem-91 29 32         SPACE eurjchem-91 29 33 ( ( PUNCT eurjchem-91 29 34 0.21 0.21 NUM eurjchem-91 29 35     SPACE eurjchem-91 29 36 ml ml NOUN eurjchem-91 29 37 , , PUNCT eurjchem-91 29 38     SPACE eurjchem-91 29 39 2 2 NUM eurjchem-91 29 40     SPACE eurjchem-91 29 41 mmol mmol NOUN eurjchem-91 29 42 ) ) PUNCT eurjchem-91 29 43 , , PUNCT eurjchem-91 29 44     SPACE eurjchem-91 29 45 in in ADP eurjchem-91 29 46     SPACE eurjchem-91 29 47 glacial glacial ADJ eurjchem-91 29 48     SPACE eurjchem-91 29 49 acetic acetic ADJ eurjchem-91 29 50     SPACE eurjchem-91 29 51 acid acid NOUN eurjchem-91 29 52     SPACE eurjchem-91 29 53 ( ( PUNCT eurjchem-91 29 54 10 10 NUM eurjchem-91 29 55     SPACE eurjchem-91 29 56 ml ml NOUN eurjchem-91 29 57 ) ) PUNCT eurjchem-91 29 58     SPACE eurjchem-91 29 59 and and CCONJ eurjchem-91 29 60     SPACE eurjchem-91 29 61 freshly freshly ADV eurjchem-91 29 62     SPACE eurjchem-91 29 63 fused fuse VERB eurjchem-91 29 64     SPACE eurjchem-91 29 65 sodium sodium NOUN eurjchem-91 29 66     SPACE eurjchem-91 29 67 acetate acetate NOUN eurjchem-91 29 68     SPACE eurjchem-91 29 69 ( ( PUNCT eurjchem-91 29 70 0.2 0.2 NUM eurjchem-91 29 71     SPACE eurjchem-91 29 72 g g NOUN eurjchem-91 29 73 ) ) PUNCT eurjchem-91 29 74 , , PUNCT eurjchem-91 29 75     SPACE eurjchem-91 29 76 was be AUX eurjchem-91 29 77     SPACE eurjchem-91 29 78 heated heated ADJ eurjchem-91 29 79     SPACE eurjchem-91 29 80 at at ADP eurjchem-91 29 81     SPACE eurjchem-91 29 82 reflux reflux NOUN eurjchem-91 29 83     SPACE eurjchem-91 29 84 for for ADP eurjchem-91 29 85     SPACE eurjchem-91 29 86 3h 3h NUM eurjchem-91 29 87 , , PUNCT eurjchem-91 29 88     SPACE eurjchem-91 29 89 the the DET eurjchem-91 29 90     SPACE eurjchem-91 29 91 yellow yellow ADJ eurjchem-91 29 92     SPACE eurjchem-91 29 93 crystals crystal NOUN eurjchem-91 29 94     SPACE eurjchem-91 29 95 obtained obtain VERB eurjchem-91 29 96     SPACE eurjchem-91 29 97 after after SCONJ eurjchem-91 29 98     SPACE eurjchem-91 29 99 cooling cooling NOUN eurjchem-91 29 100     SPACE eurjchem-91 29 101 were be AUX eurjchem-91 29 102     SPACE eurjchem-91 29 103 filtered filter VERB eurjchem-91 29 104     SPACE eurjchem-91 29 105 and and CCONJ eurjchem-91 29 106     SPACE eurjchem-91 29 107 recrystallized recrystallize VERB eurjchem-91 29 108     SPACE eurjchem-91 29 109 from from ADP eurjchem-91 29 110     SPACE eurjchem-91 29 111 dmf dmf PROPN eurjchem-91 29 112     SPACE eurjchem-91 29 113 to to PART eurjchem-91 29 114     SPACE eurjchem-91 29 115 give give VERB eurjchem-91 29 116     SPACE eurjchem-91 29 117 4 4 NUM eurjchem-91 29 118     SPACE eurjchem-91 29 119 as as ADV eurjchem-91 29 120     SPACE eurjchem-91 29 121 yellow yellow ADJ eurjchem-91 29 122     SPACE eurjchem-91 29 123 crystals crystal NOUN eurjchem-91 29 124     SPACE eurjchem-91 29 125 ( ( PUNCT eurjchem-91 29 126 scheme scheme NOUN eurjchem-91 29 127     SPACE eurjchem-91 29 128 2 2 NUM eurjchem-91 29 129 ) ) PUNCT eurjchem-91 29 130 . . PUNCT eurjchem-91 29 131     SPACE eurjchem-91 30 1 m.p m.p PROPN eurjchem-91 30 2 . . PROPN eurjchem-91 30 3 : : PUNCT eurjchem-91 30 4     SPACE eurjchem-91 30 5 241 241 NUM eurjchem-91 30 6     SPACE eurjchem-91 30 7 ºc ºc PROPN eurjchem-91 30 8 . . PUNCT eurjchem-91 30 9     SPACE eurjchem-91 30 10 yield yield NOUN eurjchem-91 30 11 : : PUNCT eurjchem-91 30 12     SPACE eurjchem-91 30 13 0.41 0.41 NUM eurjchem-91 30 14     SPACE eurjchem-91 30 15 g g NOUN eurjchem-91 30 16 , , PUNCT eurjchem-91 30 17     SPACE eurjchem-91 30 18 57 57 NUM eurjchem-91 30 19 % % NOUN eurjchem-91 30 20 . . PUNCT eurjchem-91 30 21     SPACE eurjchem-91 31 1 ir ir VERB eurjchem-91 31 2     SPACE eurjchem-91 31 3 ( ( PUNCT eurjchem-91 31 4 kbr kbr PROPN eurjchem-91 31 5 , , PUNCT eurjchem-91 31 6     SPACE eurjchem-91 31 7 cm‐1 cm‐1 NOUN eurjchem-91 31 8 ): ): PUNCT eurjchem-91 31 9     SPACE eurjchem-91 31 10 3430 3430 NUM eurjchem-91 31 11     SPACE eurjchem-91 31 12 ( ( PUNCT eurjchem-91 31 13 oh oh INTJ eurjchem-91 31 14 ) ) PUNCT eurjchem-91 31 15 , , PUNCT eurjchem-91 31 16     SPACE eurjchem-91 31 17 3044 3044 NUM eurjchem-91 31 18     SPACE eurjchem-91 31 19 ( ( PUNCT eurjchem-91 31 20 charom charom NOUN eurjchem-91 31 21 . . PUNCT eurjchem-91 31 22 ) ) PUNCT eurjchem-91 31 23 , , PUNCT eurjchem-91 31 24     SPACE eurjchem-91 31 25 2976 2976 NUM eurjchem-91 31 26 , , PUNCT eurjchem-91 31 27     SPACE eurjchem-91 31 28 2920 2920 NUM eurjchem-91 31 29     SPACE eurjchem-91 31 30 ( ( PUNCT eurjchem-91 31 31 ch3 ch3 PROPN eurjchem-91 31 32 , , PUNCT eurjchem-91 31 33     SPACE eurjchem-91 31 34 ch2 ch2 PROPN eurjchem-91 31 35 ) ) PUNCT eurjchem-91 31 36 , , PUNCT eurjchem-91 31 37     SPACE eurjchem-91 31 38 1725 1725 NUM eurjchem-91 31 39     SPACE eurjchem-91 31 40 ( ( PUNCT eurjchem-91 31 41 oc oc PROPN eurjchem-91 31 42 = = NOUN eurjchem-91 31 43 o o NOUN eurjchem-91 31 44 ) ) PUNCT eurjchem-91 31 45 , , PUNCT eurjchem-91 31 46     SPACE eurjchem-91 31 47 1642 1642 NUM eurjchem-91 31 48     SPACE eurjchem-91 31 49 ( ( PUNCT eurjchem-91 31 50 c c NOUN eurjchem-91 31 51 = = NOUN eurjchem-91 31 52 oquinolinone oquinolinone NOUN eurjchem-91 31 53 ) ) PUNCT eurjchem-91 31 54 , , PUNCT eurjchem-91 31 55     SPACE eurjchem-91 31 56 1611 1611 NUM eurjchem-91 31 57     SPACE eurjchem-91 31 58 ( ( PUNCT eurjchem-91 31 59 c c NOUN eurjchem-91 31 60 = = NOUN eurjchem-91 31 61 oketone oketone NOUN eurjchem-91 31 62 ) ) PUNCT eurjchem-91 31 63 . . PUNCT eurjchem-91 31 64     SPACE eurjchem-91 31 65 1h 1h NUM eurjchem-91 31 66     SPACE eurjchem-91 31 67 nmr nmr NOUN eurjchem-91 31 68     SPACE eurjchem-91 31 69 ( ( PUNCT eurjchem-91 31 70 dmso‐d6 dmso‐d6 PROPN eurjchem-91 31 71 , , PUNCT eurjchem-91 31 72     SPACE eurjchem-91 31 73 δ δ PROPN eurjchem-91 31 74 ): ): PUNCT eurjchem-91 31 75     SPACE eurjchem-91 31 76 1.13 1.13 NUM eurjchem-91 31 77     SPACE eurjchem-91 31 78 ( ( PUNCT eurjchem-91 31 79 t t PROPN eurjchem-91 31 80 , , PUNCT eurjchem-91 31 81     SPACE eurjchem-91 31 82 3h 3h NUM eurjchem-91 31 83 , , PUNCT eurjchem-91 31 84     SPACE eurjchem-91 31 85 j= j= VERB eurjchem-91 31 86     SPACE eurjchem-91 31 87 6.9 6.9 NUM eurjchem-91 31 88     SPACE eurjchem-91 31 89 hz hz VERB eurjchem-91 31 90 , , PUNCT eurjchem-91 31 91     SPACE eurjchem-91 31 92 ch3 ch3 PROPN eurjchem-91 31 93 ) ) PUNCT eurjchem-91 31 94 , , PUNCT eurjchem-91 31 95     SPACE eurjchem-91 31 96 4.13 4.13 NUM eurjchem-91 31 97     SPACE eurjchem-91 31 98 ( ( PUNCT eurjchem-91 31 99 q q ADJ eurjchem-91 31 100 , , PUNCT eurjchem-91 31 101     SPACE eurjchem-91 31 102 2h 2h NUM eurjchem-91 31 103 , , PUNCT eurjchem-91 31 104     SPACE eurjchem-91 31 105 j= j= NOUN eurjchem-91 31 106     SPACE eurjchem-91 31 107 6.9 6.9 NUM eurjchem-91 31 108     SPACE eurjchem-91 31 109 hz hz VERB eurjchem-91 31 110 , , PUNCT eurjchem-91 31 111     SPACE eurjchem-91 31 112 ch2 ch2 PROPN eurjchem-91 31 113 ) ) PUNCT eurjchem-91 31 114 , , PUNCT eurjchem-91 31 115     SPACE eurjchem-91 31 116 7.29‐ 7.29‐ NUM eurjchem-91 31 117 7.43 7.43 NUM eurjchem-91 31 118     SPACE eurjchem-91 31 119 ( ( PUNCT eurjchem-91 31 120 m m PROPN eurjchem-91 31 121 , , PUNCT eurjchem-91 31 122     SPACE eurjchem-91 31 123 4h 4h NOUN eurjchem-91 31 124 , , PUNCT eurjchem-91 31 125     SPACE eurjchem-91 31 126 ar‐h ar‐h NOUN eurjchem-91 31 127 ) ) PUNCT eurjchem-91 31 128 , , PUNCT eurjchem-91 31 129     SPACE eurjchem-91 31 130 7.54 7.54 NUM eurjchem-91 31 131     SPACE eurjchem-91 31 132 ( ( PUNCT eurjchem-91 31 133 d d PROPN eurjchem-91 31 134 , , PUNCT eurjchem-91 31 135     SPACE eurjchem-91 31 136 1h 1h NUM eurjchem-91 31 137 , , PUNCT eurjchem-91 31 138     SPACE eurjchem-91 31 139 j= j= NOUN eurjchem-91 31 140     SPACE eurjchem-91 31 141 8.4 8.4 NUM eurjchem-91 31 142     SPACE eurjchem-91 31 143 hz hz VERB eurjchem-91 31 144 , , PUNCT eurjchem-91 31 145     SPACE eurjchem-91 31 146 ar‐h ar‐h NOUN eurjchem-91 31 147 ) ) PUNCT eurjchem-91 31 148 , , PUNCT eurjchem-91 31 149     SPACE eurjchem-91 31 150 7.69 7.69 NUM eurjchem-91 31 151     SPACE eurjchem-91 31 152 ( ( PUNCT eurjchem-91 31 153 t t PROPN eurjchem-91 31 154 , , PUNCT eurjchem-91 31 155     SPACE eurjchem-91 31 156 1h 1h NUM eurjchem-91 31 157 , , PUNCT eurjchem-91 31 158     SPACE eurjchem-91 31 159 j= j= VERB eurjchem-91 31 160     SPACE eurjchem-91 31 161 7.5 7.5 NUM eurjchem-91 31 162     SPACE eurjchem-91 31 163 hz hz VERB eurjchem-91 31 164 , , PUNCT eurjchem-91 31 165     SPACE eurjchem-91 31 166 ar‐h ar‐h NOUN eurjchem-91 31 167 ) ) PUNCT eurjchem-91 31 168 , , PUNCT eurjchem-91 31 169     SPACE eurjchem-91 31 170 7.78‐7.82 7.78‐7.82 NUM eurjchem-91 31 171     SPACE eurjchem-91 31 172 ( ( PUNCT eurjchem-91 31 173 m m PROPN eurjchem-91 31 174 , , PUNCT eurjchem-91 31 175     SPACE eurjchem-91 31 176 2h 2h NUM eurjchem-91 31 177 , , PUNCT eurjchem-91 31 178     SPACE eurjchem-91 31 179 ar‐h ar‐h NOUN eurjchem-91 31 180 ) ) PUNCT eurjchem-91 31 181 , , PUNCT eurjchem-91 31 182     SPACE eurjchem-91 31 183 8.13 8.13 NUM eurjchem-91 31 184     SPACE eurjchem-91 31 185 ( ( PUNCT eurjchem-91 31 186 s s PROPN eurjchem-91 31 187 , , PUNCT eurjchem-91 31 188     SPACE eurjchem-91 31 189 1h 1h NUM eurjchem-91 31 190 , , PUNCT eurjchem-91 31 191     SPACE eurjchem-91 31 192 chmethine chmethine NOUN eurjchem-91 31 193 ) ) PUNCT eurjchem-91 31 194 . . PUNCT eurjchem-91 31 195     SPACE eurjchem-91 32 1 13c 13c NOUN eurjchem-91 32 2     SPACE eurjchem-91 32 3 nmr nmr NOUN eurjchem-91 32 4     SPACE eurjchem-91 32 5 ( ( PUNCT eurjchem-91 32 6 dmso‐d6 dmso‐d6 PROPN eurjchem-91 32 7 , , PUNCT eurjchem-91 32 8     SPACE eurjchem-91 32 9 δ δ PROPN eurjchem-91 32 10 ): ): PUNCT eurjchem-91 32 11     SPACE eurjchem-91 32 12 12.4 12.4 NUM eurjchem-91 32 13     SPACE eurjchem-91 32 14 ( ( PUNCT eurjchem-91 32 15 ch3 ch3 PROPN eurjchem-91 32 16 ) ) PUNCT eurjchem-91 32 17 , , PUNCT eurjchem-91 32 18     SPACE eurjchem-91 32 19 36.2 36.2 NUM eurjchem-91 32 20     SPACE eurjchem-91 32 21 ( ( PUNCT eurjchem-91 32 22 ch2 ch2 PROPN eurjchem-91 32 23 ) ) PUNCT eurjchem-91 32 24 , , PUNCT eurjchem-91 32 25     SPACE eurjchem-91 32 26 106.5 106.5 NUM eurjchem-91 32 27     SPACE eurjchem-91 32 28 ( ( PUNCT eurjchem-91 32 29 c4a c4a ADJ eurjchem-91 32 30 ) ) PUNCT eurjchem-91 32 31 , , PUNCT eurjchem-91 32 32     SPACE eurjchem-91 32 33 114.8 114.8 NUM eurjchem-91 32 34     SPACE eurjchem-91 32 35 ( ( PUNCT eurjchem-91 32 36 c7 c7 PROPN eurjchem-91 32 37 ) ) PUNCT eurjchem-91 32 38 , , PUNCT eurjchem-91 32 39     SPACE eurjchem-91 32 40 116.1 116.1 NUM eurjchem-91 32 41     SPACE eurjchem-91 32 42 ( ( PUNCT eurjchem-91 32 43 c3 c3 PROPN eurjchem-91 32 44 ` ` PROPN eurjchem-91 32 45 ) ) PUNCT eurjchem-91 32 46 , , PUNCT eurjchem-91 32 47     SPACE eurjchem-91 32 48 118.3 118.3 NUM eurjchem-91 32 49     SPACE eurjchem-91 32 50 ( ( PUNCT eurjchem-91 32 51 c5 c5 PROPN eurjchem-91 32 52 ` ` PUNCT eurjchem-91 32 53 ) ) PUNCT eurjchem-91 32 54 , , PUNCT eurjchem-91 32 55     SPACE eurjchem-91 32 56 120.5 120.5 NUM eurjchem-91 32 57     SPACE eurjchem-91 32 58 ( ( PUNCT eurjchem-91 32 59 c10a c10a PROPN eurjchem-91 32 60 ) ) PUNCT eurjchem-91 32 61 , , PUNCT eurjchem-91 32 62     SPACE eurjchem-91 32 63 122.1 122.1 NUM eurjchem-91 32 64     SPACE eurjchem-91 32 65 ( ( PUNCT eurjchem-91 32 66 c9 c9 NOUN eurjchem-91 32 67 ) ) PUNCT eurjchem-91 32 68 , , PUNCT eurjchem-91 32 69     SPACE eurjchem-91 32 70 125.6 125.6 NUM eurjchem-91 32 71     SPACE eurjchem-91 32 72 ( ( PUNCT eurjchem-91 32 73 c4 c4 NOUN eurjchem-91 32 74 ` ` PUNCT eurjchem-91 32 75 ) ) PUNCT eurjchem-91 32 76 , , PUNCT eurjchem-91 32 77     SPACE eurjchem-91 32 78 125.3 125.3 NUM eurjchem-91 32 79     SPACE eurjchem-91 32 80 ( ( PUNCT eurjchem-91 32 81 c6 c6 PROPN eurjchem-91 32 82 ` ` PUNCT eurjchem-91 32 83 ) ) PUNCT eurjchem-91 32 84 , , PUNCT eurjchem-91 32 85     SPACE eurjchem-91 32 86 129.1 129.1 NUM eurjchem-91 32 87     SPACE eurjchem-91 32 88 ( ( PUNCT eurjchem-91 32 89 c8 c8 PROPN eurjchem-91 32 90 ) ) PUNCT eurjchem-91 32 91 , , PUNCT eurjchem-91 32 92     SPACE eurjchem-91 32 93 130.1 130.1 NUM eurjchem-91 32 94     SPACE eurjchem-91 32 95 ( ( PUNCT eurjchem-91 32 96 c10 c10 PROPN eurjchem-91 32 97 ) ) PUNCT eurjchem-91 32 98 , , PUNCT eurjchem-91 32 99     SPACE eurjchem-91 32 100 132.5 132.5 NUM eurjchem-91 32 101     SPACE eurjchem-91 32 102 ( ( PUNCT eurjchem-91 32 103 c3 c3 PROPN eurjchem-91 32 104 ) ) PUNCT eurjchem-91 32 105 , , PUNCT eurjchem-91 32 106     SPACE eurjchem-91 32 107 135.2 135.2 NUM eurjchem-91 32 108     SPACE eurjchem-91 32 109 ( ( PUNCT eurjchem-91 32 110 c1 c1 PROPN eurjchem-91 32 111 ` ` PUNCT eurjchem-91 32 112 ) ) PUNCT eurjchem-91 32 113 , , PUNCT eurjchem-91 32 114     SPACE eurjchem-91 32 115 139.0 139.0 NUM eurjchem-91 32 116     SPACE eurjchem-91 32 117 ( ( PUNCT eurjchem-91 32 118 c6a c6a NOUN eurjchem-91 32 119 ) ) PUNCT eurjchem-91 32 120 , , PUNCT eurjchem-91 32 121     SPACE eurjchem-91 32 122 140.4 140.4 NUM eurjchem-91 32 123     SPACE eurjchem-91 32 124 ( ( PUNCT eurjchem-91 32 125 chmethine chmethine PROPN eurjchem-91 32 126 ) ) PUNCT eurjchem-91 32 127 , , PUNCT eurjchem-91 32 128     SPACE eurjchem-91 32 129 153.3 153.3 NUM eurjchem-91 32 130     SPACE eurjchem-91 32 131 ( ( PUNCT eurjchem-91 32 132 c10b c10b NOUN eurjchem-91 32 133     SPACE eurjchem-91 32 134 as as ADP eurjchem-91 32 135     SPACE eurjchem-91 32 136 c‐o c‐o NOUN eurjchem-91 32 137 ) ) PUNCT eurjchem-91 32 138 , , PUNCT eurjchem-91 32 139     SPACE eurjchem-91 32 140 157.4 157.4 NUM eurjchem-91 32 141     SPACE eurjchem-91 32 142 ( ( PUNCT eurjchem-91 32 143 c2 c2 PROPN eurjchem-91 32 144 ` ` PUNCT eurjchem-91 32 145 ) ) PUNCT eurjchem-91 32 146 , , PUNCT eurjchem-91 32 147     SPACE eurjchem-91 32 148 168.9 168.9 NUM eurjchem-91 32 149     SPACE eurjchem-91 32 150 ( ( PUNCT eurjchem-91 32 151 c5 c5 PROPN eurjchem-91 32 152     SPACE eurjchem-91 32 153 as as ADP eurjchem-91 32 154     SPACE eurjchem-91 32 155 c c NOUN eurjchem-91 32 156 = = NOUN eurjchem-91 32 157 o o NOUN eurjchem-91 32 158 ) ) PUNCT eurjchem-91 32 159 , , PUNCT eurjchem-91 32 160     SPACE eurjchem-91 32 161 173.3 173.3 NUM eurjchem-91 32 162     SPACE eurjchem-91 32 163 ( ( PUNCT eurjchem-91 32 164 c2 c2 PROPN eurjchem-91 32 165     SPACE eurjchem-91 32 166 as as ADP eurjchem-91 32 167     SPACE eurjchem-91 32 168 c c NOUN eurjchem-91 32 169 = = NOUN eurjchem-91 32 170 o o NOUN eurjchem-91 32 171 ) ) PUNCT eurjchem-91 32 172 , , PUNCT eurjchem-91 32 173     SPACE eurjchem-91 32 174 201.5 201.5 NUM eurjchem-91 32 175     SPACE eurjchem-91 32 176 ( ( PUNCT eurjchem-91 32 177 c4 c4 NOUN eurjchem-91 32 178     SPACE eurjchem-91 32 179 as as ADP eurjchem-91 32 180     SPACE eurjchem-91 32 181 c c NOUN eurjchem-91 32 182 = = NOUN eurjchem-91 32 183 o o NOUN eurjchem-91 32 184 ) ) PUNCT eurjchem-91 32 185 . . PUNCT eurjchem-91 32 186     SPACE eurjchem-91 33 1 m m VERB eurjchem-91 33 2 / / SYM eurjchem-91 33 3 z z NOUN eurjchem-91 33 4     SPACE eurjchem-91 33 5 ( ( PUNCT eurjchem-91 33 6 relative relative ADJ eurjchem-91 33 7     SPACE eurjchem-91 33 8 intensity intensity NOUN eurjchem-91 33 9 ): ): PUNCT eurjchem-91 33 10     SPACE eurjchem-91 33 11 362 362 NUM eurjchem-91 33 12     SPACE eurjchem-91 33 13 ( ( PUNCT eurjchem-91 33 14 m+ m+ NOUN eurjchem-91 33 15     SPACE eurjchem-91 33 16 +1 +1 PROPN eurjchem-91 33 17 , , PUNCT eurjchem-91 33 18     SPACE eurjchem-91 33 19 28 28 NUM eurjchem-91 33 20 ) ) PUNCT eurjchem-91 33 21 , , PUNCT eurjchem-91 33 22     SPACE eurjchem-91 33 23 361 361 NUM eurjchem-91 33 24     SPACE eurjchem-91 33 25 ( ( PUNCT eurjchem-91 33 26 m+ m+ NUM eurjchem-91 33 27 , , PUNCT eurjchem-91 33 28     SPACE eurjchem-91 33 29 100 100 NUM eurjchem-91 33 30 ) ) PUNCT eurjchem-91 33 31 , , PUNCT eurjchem-91 33 32     SPACE eurjchem-91 33 33 332 332 NUM eurjchem-91 33 34     SPACE eurjchem-91 33 35 ( ( PUNCT eurjchem-91 33 36 22 22 NUM eurjchem-91 33 37 ) ) PUNCT eurjchem-91 33 38 , , PUNCT eurjchem-91 33 39     SPACE eurjchem-91 33 40 304 304 NUM eurjchem-91 33 41     SPACE eurjchem-91 33 42 ( ( PUNCT eurjchem-91 33 43 11 11 NUM eurjchem-91 33 44 ) ) PUNCT eurjchem-91 33 45 , , PUNCT eurjchem-91 33 46     SPACE eurjchem-91 33 47 288 288 NUM eurjchem-91 33 48     SPACE eurjchem-91 33 49 ( ( PUNCT eurjchem-91 33 50 67 67 NUM eurjchem-91 33 51 ) ) PUNCT eurjchem-91 33 52 , , PUNCT eurjchem-91 33 53     SPACE eurjchem-91 33 54 261 261 NUM eurjchem-91 33 55     SPACE eurjchem-91 33 56 ( ( PUNCT eurjchem-91 33 57 11 11 NUM eurjchem-91 33 58 ) ) PUNCT eurjchem-91 33 59 , , PUNCT eurjchem-91 33 60     SPACE eurjchem-91 33 61 188 188 NUM eurjchem-91 33 62     SPACE eurjchem-91 33 63 ( ( PUNCT eurjchem-91 33 64 25 25 NUM eurjchem-91 33 65 ) ) PUNCT eurjchem-91 33 66 , , PUNCT eurjchem-91 33 67     SPACE eurjchem-91 33 68 160 160 NUM eurjchem-91 33 69     SPACE eurjchem-91 33 70 ( ( PUNCT eurjchem-91 33 71 8) 8) NUM eurjchem-91 33 72 , , PUNCT eurjchem-91 33 73     SPACE eurjchem-91 33 74 132 132 NUM eurjchem-91 33 75     SPACE eurjchem-91 33 76 ( ( PUNCT eurjchem-91 33 77 10 10 NUM eurjchem-91 33 78 ) ) PUNCT eurjchem-91 33 79 , , PUNCT eurjchem-91 33 80     SPACE eurjchem-91 33 81 118 118 NUM eurjchem-91 33 82     SPACE eurjchem-91 33 83 ( ( PUNCT eurjchem-91 33 84 6 6 NUM eurjchem-91 33 85 ) ) PUNCT eurjchem-91 33 86 , , PUNCT eurjchem-91 33 87     SPACE eurjchem-91 33 88 101 101 NUM eurjchem-91 33 89     SPACE eurjchem-91 33 90 ( ( PUNCT eurjchem-91 33 91 3 3 NUM eurjchem-91 33 92 ) ) PUNCT eurjchem-91 33 93 , , PUNCT eurjchem-91 33 94     SPACE eurjchem-91 33 95 77 77 NUM eurjchem-91 33 96     SPACE eurjchem-91 33 97 ( ( PUNCT eurjchem-91 33 98 2 2 NUM eurjchem-91 33 99 ) ) PUNCT eurjchem-91 33 100 . . PUNCT eurjchem-91 33 101     SPACE eurjchem-91 34 1 anal anal ADJ eurjchem-91 34 2 . . PUNCT eurjchem-91 34 3     SPACE eurjchem-91 34 4 calcd calcd NOUN eurjchem-91 34 5     SPACE eurjchem-91 34 6 for for ADP eurjchem-91 34 7     SPACE eurjchem-91 34 8 c21h15no5 c21h15no5 NOUN eurjchem-91 34 9     SPACE eurjchem-91 34 10 ( ( PUNCT eurjchem-91 34 11 361.35 361.35 NUM eurjchem-91 34 12 ): ): PUNCT eurjchem-91 34 13     SPACE eurjchem-91 34 14 c c NOUN eurjchem-91 34 15 , , PUNCT eurjchem-91 34 16     SPACE eurjchem-91 34 17 69.80 69.80 NUM eurjchem-91 34 18 ; ; PUNCT eurjchem-91 34 19     SPACE eurjchem-91 34 20 h h NOUN eurjchem-91 34 21 , , PUNCT eurjchem-91 34 22     SPACE eurjchem-91 34 23 4.18 4.18 NUM eurjchem-91 34 24 ; ; PUNCT eurjchem-91 34 25     SPACE eurjchem-91 34 26 n n CCONJ eurjchem-91 34 27 , , PUNCT eurjchem-91 34 28     SPACE eurjchem-91 34 29 3.88 3.88 NUM eurjchem-91 34 30 % % NOUN eurjchem-91 34 31 . . PUNCT eurjchem-91 34 32     SPACE eurjchem-91 34 33 found find VERB eurjchem-91 34 34 : : PUNCT eurjchem-91 34 35     SPACE eurjchem-91 34 36 c c X eurjchem-91 34 37 , , PUNCT eurjchem-91 34 38     SPACE eurjchem-91 34 39 69.43 69.43 NUM eurjchem-91 34 40 ; ; PUNCT eurjchem-91 34 41     SPACE eurjchem-91 34 42 h h NOUN eurjchem-91 34 43 , , PUNCT eurjchem-91 34 44     SPACE eurjchem-91 34 45 4.26 4.26 NUM eurjchem-91 34 46 ; ; PUNCT eurjchem-91 34 47     SPACE eurjchem-91 34 48 n n CCONJ eurjchem-91 34 49 , , PUNCT eurjchem-91 34 50     SPACE eurjchem-91 34 51 3.79 3.79 NUM eurjchem-91 34 52 % % NOUN eurjchem-91 34 53 . . PUNCT eurjchem-91 34 54         SPACE eurjchem-91 35 1 2.5 2.5 NUM eurjchem-91 35 2 . . PUNCT eurjchem-91 35 3     SPACE eurjchem-91 36 1 2­[(1­ethyl­4­hydroxy­2­oxo­1,2­dihydro­quinolin­3­ 2­[(1­ethyl­4­hydroxy­2­oxo­1,2­dihydro­quinolin­3­ PROPN eurjchem-91 36 2 yl)carbonyl]­3­(1­hydroxy yl)carbonyl]­3­(1­hydroxy PROPN eurjchem-91 36 3     SPACE eurjchem-91 36 4 naphthalen­2­yl)­prop­2­enoic naphthalen­2­yl)­prop­2­enoic NOUN eurjchem-91 36 5     SPACE eurjchem-91 36 6 acid acid NOUN eurjchem-91 36 7     SPACE eurjchem-91 36 8 ( ( PUNCT eurjchem-91 36 9 6 6 NUM eurjchem-91 36 10 ) ) PUNCT eurjchem-91 36 11         SPACE eurjchem-91 36 12 a a DET eurjchem-91 36 13     SPACE eurjchem-91 36 14 mixture mixture NOUN eurjchem-91 36 15     SPACE eurjchem-91 36 16 of of ADP eurjchem-91 36 17     SPACE eurjchem-91 36 18 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 36 19     SPACE eurjchem-91 36 20 2 2 NUM eurjchem-91 36 21     SPACE eurjchem-91 36 22 ( ( PUNCT eurjchem-91 36 23 0.55 0.55 NUM eurjchem-91 36 24     SPACE eurjchem-91 36 25 g g NOUN eurjchem-91 36 26 , , PUNCT eurjchem-91 36 27     SPACE eurjchem-91 36 28 2 2 NUM eurjchem-91 36 29     SPACE eurjchem-91 36 30 mmol mmol NOUN eurjchem-91 36 31 ) ) PUNCT eurjchem-91 36 32     SPACE eurjchem-91 36 33 and and CCONJ eurjchem-91 36 34     SPACE eurjchem-91 36 35 2‐hydroxy‐ 2‐hydroxy‐ NUM eurjchem-91 36 36 1‐naphthaldehyde 1‐naphthaldehyde NUM eurjchem-91 36 37     SPACE eurjchem-91 36 38 ( ( PUNCT eurjchem-91 36 39 0.344 0.344 NOUN eurjchem-91 36 40     SPACE eurjchem-91 36 41 g g NOUN eurjchem-91 36 42 , , PUNCT eurjchem-91 36 43     SPACE eurjchem-91 36 44 2 2 NUM eurjchem-91 36 45     SPACE eurjchem-91 36 46 mmol mmol NOUN eurjchem-91 36 47 ) ) PUNCT eurjchem-91 36 48 , , PUNCT eurjchem-91 36 49     SPACE eurjchem-91 36 50 in in ADP eurjchem-91 36 51     SPACE eurjchem-91 36 52 glacial glacial ADJ eurjchem-91 36 53     SPACE eurjchem-91 36 54 acetic acetic ADJ eurjchem-91 36 55     SPACE eurjchem-91 36 56 acid acid NOUN eurjchem-91 36 57     SPACE eurjchem-91 36 58 ( ( PUNCT eurjchem-91 36 59 10 10 NUM eurjchem-91 36 60     SPACE eurjchem-91 36 61 ml ml NOUN eurjchem-91 36 62 ) ) PUNCT eurjchem-91 36 63     SPACE eurjchem-91 36 64 and and CCONJ eurjchem-91 36 65     SPACE eurjchem-91 36 66 freshly freshly ADV eurjchem-91 36 67     SPACE eurjchem-91 36 68 fused fuse VERB eurjchem-91 36 69     SPACE eurjchem-91 36 70 sodium sodium NOUN eurjchem-91 36 71     SPACE eurjchem-91 36 72 acetate acetate NOUN eurjchem-91 36 73     SPACE eurjchem-91 36 74 ( ( PUNCT eurjchem-91 36 75 0.2 0.2 NUM eurjchem-91 36 76     SPACE eurjchem-91 36 77 g g NOUN eurjchem-91 36 78 ) ) PUNCT eurjchem-91 36 79 , , PUNCT eurjchem-91 36 80     SPACE eurjchem-91 36 81 was be AUX eurjchem-91 36 82     SPACE eurjchem-91 36 83 heated heated ADJ eurjchem-91 36 84     SPACE eurjchem-91 36 85 under under ADP eurjchem-91 36 86     SPACE eurjchem-91 36 87 reflux reflux NOUN eurjchem-91 36 88     SPACE eurjchem-91 36 89 for for ADP eurjchem-91 36 90     SPACE eurjchem-91 36 91 4h 4h NOUN eurjchem-91 36 92     SPACE eurjchem-91 36 93 ( ( PUNCT eurjchem-91 36 94 scheme scheme NOUN eurjchem-91 36 95     SPACE eurjchem-91 36 96 3 3 NUM eurjchem-91 36 97 ) ) PUNCT eurjchem-91 36 98 . . PUNCT eurjchem-91 36 99     SPACE eurjchem-91 37 1 the the DET eurjchem-91 37 2     SPACE eurjchem-91 37 3 yellow yellow ADJ eurjchem-91 37 4     SPACE eurjchem-91 37 5 crystals crystal NOUN eurjchem-91 37 6     SPACE eurjchem-91 37 7 obtained obtain VERB eurjchem-91 37 8     SPACE eurjchem-91 37 9 after after SCONJ eurjchem-91 37 10     SPACE eurjchem-91 37 11 cooling cooling NOUN eurjchem-91 37 12     SPACE eurjchem-91 37 13 were be AUX eurjchem-91 37 14     SPACE eurjchem-91 37 15 filtered filter VERB eurjchem-91 37 16     SPACE eurjchem-91 37 17 and and CCONJ eurjchem-91 37 18     SPACE eurjchem-91 37 19 recrystallized recrystallize VERB eurjchem-91 37 20     SPACE eurjchem-91 37 21 from from ADP eurjchem-91 37 22     SPACE eurjchem-91 37 23 acetic acetic ADJ eurjchem-91 37 24     SPACE eurjchem-91 37 25 acid acid NOUN eurjchem-91 37 26     SPACE eurjchem-91 37 27 to to PART eurjchem-91 37 28     SPACE eurjchem-91 37 29 give give VERB eurjchem-91 37 30     SPACE eurjchem-91 37 31 6 6 NUM eurjchem-91 37 32     SPACE eurjchem-91 37 33 as as ADP eurjchem-91 37 34     SPACE eurjchem-91 37 35 yellow yellow ADJ eurjchem-91 37 36     SPACE eurjchem-91 37 37 crystals crystal NOUN eurjchem-91 37 38 . . PUNCT eurjchem-91 37 39     SPACE eurjchem-91 38 1 m.p m.p PROPN eurjchem-91 38 2 . . PROPN eurjchem-91 38 3 : : PUNCT eurjchem-91 38 4     SPACE eurjchem-91 38 5 280 280 NUM eurjchem-91 38 6     SPACE eurjchem-91 38 7 ºc ºc PROPN eurjchem-91 38 8 . . PUNCT eurjchem-91 38 9     SPACE eurjchem-91 38 10 yield yield NOUN eurjchem-91 38 11 : : PUNCT eurjchem-91 38 12     SPACE eurjchem-91 38 13 0.39 0.39 NUM eurjchem-91 38 14     SPACE eurjchem-91 38 15 g g NOUN eurjchem-91 38 16 , , PUNCT eurjchem-91 38 17     SPACE eurjchem-91 38 18 45 45 NUM eurjchem-91 38 19 % % NOUN eurjchem-91 38 20 . . PUNCT eurjchem-91 38 21     SPACE eurjchem-91 39 1 ir ir VERB eurjchem-91 39 2     SPACE eurjchem-91 39 3 ( ( PUNCT eurjchem-91 39 4 kbr kbr PROPN eurjchem-91 39 5 , , PUNCT eurjchem-91 39 6     SPACE eurjchem-91 39 7 cm‐1 cm‐1 NOUN eurjchem-91 39 8 ): ): PUNCT eurjchem-91 39 9     SPACE eurjchem-91 39 10 3496 3496 NUM eurjchem-91 39 11 , , PUNCT eurjchem-91 39 12     SPACE eurjchem-91 39 13 3350 3350 NUM eurjchem-91 39 14 , , PUNCT eurjchem-91 39 15     SPACE eurjchem-91 39 16 3200 3200 NUM eurjchem-91 39 17     SPACE eurjchem-91 39 18 ( ( PUNCT eurjchem-91 39 19 3oh 3oh NOUN eurjchem-91 39 20 ) ) PUNCT eurjchem-91 39 21 , , PUNCT eurjchem-91 39 22     SPACE eurjchem-91 39 23 3063 3063 NUM eurjchem-91 39 24     SPACE eurjchem-91 39 25 ( ( PUNCT eurjchem-91 39 26 charom charom NOUN eurjchem-91 39 27 . . PUNCT eurjchem-91 39 28 ) ) PUNCT eurjchem-91 39 29 , , PUNCT eurjchem-91 39 30     SPACE eurjchem-91 39 31 2979 2979 NUM eurjchem-91 39 32 , , PUNCT eurjchem-91 39 33     SPACE eurjchem-91 39 34 2885 2885 NUM eurjchem-91 39 35     SPACE eurjchem-91 39 36 ( ( PUNCT eurjchem-91 39 37 ch3 ch3 PROPN eurjchem-91 39 38 , , PUNCT eurjchem-91 39 39     SPACE eurjchem-91 39 40 ch2 ch2 PROPN eurjchem-91 39 41 ) ) PUNCT eurjchem-91 39 42 , , PUNCT eurjchem-91 39 43     SPACE eurjchem-91 39 44 1719 1719 NUM eurjchem-91 39 45     SPACE eurjchem-91 39 46 ( ( PUNCT eurjchem-91 39 47 c c NOUN eurjchem-91 39 48 = = NOUN eurjchem-91 39 49 ocarboxy ocarboxy ADJ eurjchem-91 39 50 ) ) PUNCT eurjchem-91 39 51 , , PUNCT eurjchem-91 39 52     SPACE eurjchem-91 39 53 1617 1617 NUM eurjchem-91 39 54     SPACE eurjchem-91 39 55 ( ( PUNCT eurjchem-91 39 56 c c NOUN eurjchem-91 39 57 = = NOUN eurjchem-91 39 58 oquinolinone oquinolinone NOUN eurjchem-91 39 59     SPACE eurjchem-91 39 60 and and CCONJ eurjchem-91 39 61     SPACE eurjchem-91 39 62 c c NOUN eurjchem-91 39 63 = = NOUN eurjchem-91 39 64 oketone oketone NOUN eurjchem-91 39 65 ) ) PUNCT eurjchem-91 39 66 . . PUNCT eurjchem-91 39 67     SPACE eurjchem-91 39 68 1h 1h NUM eurjchem-91 39 69     SPACE eurjchem-91 39 70 nmr nmr NOUN eurjchem-91 39 71     SPACE eurjchem-91 39 72 ( ( PUNCT eurjchem-91 39 73 dmso‐d6 dmso‐d6 PROPN eurjchem-91 39 74 , , PUNCT eurjchem-91 39 75     SPACE eurjchem-91 39 76 δ δ PROPN eurjchem-91 39 77 ): ): PUNCT eurjchem-91 39 78     SPACE eurjchem-91 39 79 1.13 1.13 NUM eurjchem-91 39 80     SPACE eurjchem-91 39 81 ( ( PUNCT eurjchem-91 39 82 t t PROPN eurjchem-91 39 83 , , PUNCT eurjchem-91 39 84     SPACE eurjchem-91 39 85 3h 3h NUM eurjchem-91 39 86 , , PUNCT eurjchem-91 39 87     SPACE eurjchem-91 39 88 j=7.8 j=7.8 NOUN eurjchem-91 39 89     SPACE eurjchem-91 39 90 hz hz VERB eurjchem-91 39 91 , , PUNCT eurjchem-91 39 92     SPACE eurjchem-91 39 93 ch3 ch3 PROPN eurjchem-91 39 94 ) ) PUNCT eurjchem-91 39 95 , , PUNCT eurjchem-91 39 96     SPACE eurjchem-91 39 97 4.14 4.14 NUM eurjchem-91 39 98     SPACE eurjchem-91 39 99 ( ( PUNCT eurjchem-91 39 100 q q ADJ eurjchem-91 39 101 , , PUNCT eurjchem-91 39 102     SPACE eurjchem-91 39 103 2h 2h NUM eurjchem-91 39 104 , , PUNCT eurjchem-91 39 105     SPACE eurjchem-91 39 106 j=7.8 j=7.8 NOUN eurjchem-91 39 107     SPACE eurjchem-91 39 108 hz hz VERB eurjchem-91 39 109 , , PUNCT eurjchem-91 39 110     SPACE eurjchem-91 39 111 ch2 ch2 PROPN eurjchem-91 39 112 ) ) PUNCT eurjchem-91 39 113 , , PUNCT eurjchem-91 39 114     SPACE eurjchem-91 39 115 5.60 5.60 NUM eurjchem-91 39 116     SPACE eurjchem-91 39 117 ( ( PUNCT eurjchem-91 39 118 s s PROPN eurjchem-91 39 119 , , PUNCT eurjchem-91 39 120     SPACE eurjchem-91 39 121 1h 1h NUM eurjchem-91 39 122 , , PUNCT eurjchem-91 39 123     SPACE eurjchem-91 39 124 chmethine chmethine NOUN eurjchem-91 39 125 ) ) PUNCT eurjchem-91 39 126 , , PUNCT eurjchem-91 39 127     SPACE eurjchem-91 39 128 7.33‐8.10 7.33‐8.10 NOUN eurjchem-91 39 129     SPACE eurjchem-91 39 130 ( ( PUNCT eurjchem-91 39 131 m m PROPN eurjchem-91 39 132 , , PUNCT eurjchem-91 39 133     SPACE eurjchem-91 39 134 8h 8h NUM eurjchem-91 39 135 , , PUNCT eurjchem-91 39 136     SPACE eurjchem-91 39 137 ar‐h ar‐h NOUN eurjchem-91 39 138 ) ) PUNCT eurjchem-91 39 139 , , PUNCT eurjchem-91 39 140     SPACE eurjchem-91 39 141 8.58‐8.91 8.58‐8.91 NOUN eurjchem-91 39 142     SPACE eurjchem-91 39 143 ( ( PUNCT eurjchem-91 39 144 m m PROPN eurjchem-91 39 145 , , PUNCT eurjchem-91 39 146     SPACE eurjchem-91 39 147 2h 2h NUM eurjchem-91 39 148 , , PUNCT eurjchem-91 39 149     SPACE eurjchem-91 39 150 chmethine chmethine NOUN eurjchem-91 39 151 ) ) PUNCT eurjchem-91 39 152 , , PUNCT eurjchem-91 39 153     SPACE eurjchem-91 39 154 10.81 10.81 NUM eurjchem-91 39 155     SPACE eurjchem-91 39 156 ( ( PUNCT eurjchem-91 39 157 br br PROPN eurjchem-91 39 158 , , PUNCT eurjchem-91 39 159     SPACE eurjchem-91 39 160 1h 1h NUM eurjchem-91 39 161     SPACE eurjchem-91 39 162 exchangeable exchangeable ADJ eurjchem-91 39 163     SPACE eurjchem-91 39 164 with with ADP eurjchem-91 39 165     SPACE eurjchem-91 39 166 d2o d2o NOUN eurjchem-91 39 167 , , PUNCT eurjchem-91 39 168     SPACE eurjchem-91 39 169 ohnaphthalene ohnaphthalene NOUN eurjchem-91 39 170 ) ) PUNCT eurjchem-91 39 171 , , PUNCT eurjchem-91 39 172     SPACE eurjchem-91 39 173 13.50 13.50 NUM eurjchem-91 39 174     SPACE eurjchem-91 39 175 ( ( PUNCT eurjchem-91 39 176 br br PROPN eurjchem-91 39 177 , , PUNCT eurjchem-91 39 178     SPACE eurjchem-91 39 179 2h 2h NUM eurjchem-91 39 180     SPACE eurjchem-91 39 181 exchangeable exchangeable ADJ eurjchem-91 39 182     SPACE eurjchem-91 39 183 with with ADP eurjchem-91 39 184     SPACE eurjchem-91 39 185 d2o d2o NOUN eurjchem-91 39 186 , , PUNCT eurjchem-91 39 187     SPACE eurjchem-91 39 188 ohquinolinone ohquinolinone NOUN eurjchem-91 39 189     SPACE eurjchem-91 39 190 and and CCONJ eurjchem-91 39 191     SPACE eurjchem-91 39 192 ohcarboxy ohcarboxy NOUN eurjchem-91 39 193 ) ) PUNCT eurjchem-91 39 194 . . PUNCT eurjchem-91 39 195     SPACE eurjchem-91 40 1 anal anal ADJ eurjchem-91 40 2 . . PUNCT eurjchem-91 40 3     SPACE eurjchem-91 40 4 calcd calcd NOUN eurjchem-91 40 5     SPACE eurjchem-91 40 6 for for ADP eurjchem-91 40 7     SPACE eurjchem-91 40 8 c25h19no6 c25h19no6 NOUN eurjchem-91 40 9     SPACE eurjchem-91 40 10 ( ( PUNCT eurjchem-91 40 11 429.43 429.43 NUM eurjchem-91 40 12 ): ): PUNCT eurjchem-91 40 13     SPACE eurjchem-91 40 14 c c NOUN eurjchem-91 40 15 , , PUNCT eurjchem-91 40 16     SPACE eurjchem-91 40 17 69.92 69.92 NUM eurjchem-91 40 18 ; ; PUNCT eurjchem-91 40 19     SPACE eurjchem-91 40 20 h h NOUN eurjchem-91 40 21 , , PUNCT eurjchem-91 40 22     SPACE eurjchem-91 40 23 4.46 4.46 NUM eurjchem-91 40 24 ; ; PUNCT eurjchem-91 40 25     SPACE eurjchem-91 40 26 n n CCONJ eurjchem-91 40 27 , , PUNCT eurjchem-91 40 28     SPACE eurjchem-91 40 29 3.26 3.26 NUM eurjchem-91 40 30 % % NOUN eurjchem-91 40 31 . . PUNCT eurjchem-91 40 32     SPACE eurjchem-91 40 33 found find VERB eurjchem-91 40 34 : : PUNCT eurjchem-91 40 35     SPACE eurjchem-91 40 36 c c X eurjchem-91 40 37 , , PUNCT eurjchem-91 40 38     SPACE eurjchem-91 40 39 69.60 69.60 NUM eurjchem-91 40 40 ; ; PUNCT eurjchem-91 40 41     SPACE eurjchem-91 40 42 h h NOUN eurjchem-91 40 43 , , PUNCT eurjchem-91 40 44     SPACE eurjchem-91 40 45 4.60 4.60 NUM eurjchem-91 40 46 ; ; PUNCT eurjchem-91 40 47     SPACE eurjchem-91 40 48 n n CCONJ eurjchem-91 40 49 , , PUNCT eurjchem-91 40 50     SPACE eurjchem-91 40 51 3.08 3.08 NUM eurjchem-91 40 52 % % NOUN eurjchem-91 40 53 . . PUNCT eurjchem-91 40 54         SPACE eurjchem-91 41 1 scheme scheme NOUN eurjchem-91 41 2     SPACE eurjchem-91 41 3 3 3 NUM eurjchem-91 41 4         SPACE eurjchem-91 41 5 2.6 2.6 NUM eurjchem-91 41 6 . . PUNCT eurjchem-91 41 7     SPACE eurjchem-91 41 8 6­ethyl­3­[(2­hydroxynaphthalen­1­yl)methylidene)]­ 6­ethyl­3­[(2­hydroxynaphthalen­1­yl)methylidene)]­ NUM eurjchem-91 41 9 2h­pyrano[3,2­c]quinoline­2,4,5(3h,6h)trione 2h­pyrano[3,2­c]quinoline­2,4,5(3h,6h)trione NUM eurjchem-91 41 10     SPACE eurjchem-91 41 11 ( ( PUNCT eurjchem-91 41 12 7 7 NUM eurjchem-91 41 13 ) ) PUNCT eurjchem-91 41 14         SPACE eurjchem-91 41 15 2.6.1 2.6.1 NUM eurjchem-91 41 16 . . PUNCT eurjchem-91 41 17     SPACE eurjchem-91 41 18 method method VERB eurjchem-91 41 19     SPACE eurjchem-91 41 20 a a DET eurjchem-91 41 21         SPACE eurjchem-91 41 22 compound compound NOUN eurjchem-91 41 23     SPACE eurjchem-91 41 24 6 6 NUM eurjchem-91 41 25     SPACE eurjchem-91 41 26 ( ( PUNCT eurjchem-91 41 27 0.429 0.429 NUM eurjchem-91 41 28     SPACE eurjchem-91 41 29 g g NOUN eurjchem-91 41 30 , , PUNCT eurjchem-91 41 31     SPACE eurjchem-91 41 32 1 1 NUM eurjchem-91 41 33     SPACE eurjchem-91 41 34 mmol mmol NOUN eurjchem-91 41 35 ) ) PUNCT eurjchem-91 41 36     SPACE eurjchem-91 41 37 in in ADP eurjchem-91 41 38     SPACE eurjchem-91 41 39 concentrated concentrate VERB eurjchem-91 41 40     SPACE eurjchem-91 41 41 h2so4 h2so4 PROPN eurjchem-91 41 42     SPACE eurjchem-91 41 43 ( ( PUNCT eurjchem-91 41 44 5 5 NUM eurjchem-91 41 45     SPACE eurjchem-91 41 46 ml ml NOUN eurjchem-91 41 47 ) ) PUNCT eurjchem-91 41 48     SPACE eurjchem-91 41 49 was be AUX eurjchem-91 41 50     SPACE eurjchem-91 41 51 heated heated ADJ eurjchem-91 41 52     SPACE eurjchem-91 41 53 on on ADP eurjchem-91 41 54     SPACE eurjchem-91 41 55 a a DET eurjchem-91 41 56     SPACE eurjchem-91 41 57 water water NOUN eurjchem-91 41 58     SPACE eurjchem-91 41 59 bath bath NOUN eurjchem-91 41 60     SPACE eurjchem-91 41 61 for for ADP eurjchem-91 41 62     SPACE eurjchem-91 41 63 2h 2h NUM eurjchem-91 41 64 . . PUNCT eurjchem-91 41 65     SPACE eurjchem-91 41 66 after after ADP eurjchem-91 41 67     SPACE eurjchem-91 41 68 cooling cool VERB eurjchem-91 41 69     SPACE eurjchem-91 41 70 the the DET eurjchem-91 41 71     SPACE eurjchem-91 41 72 reaction reaction NOUN eurjchem-91 41 73     SPACE eurjchem-91 41 74 mixture mixture NOUN eurjchem-91 41 75     SPACE eurjchem-91 41 76 was be AUX eurjchem-91 41 77     SPACE eurjchem-91 41 78 poured pour VERB eurjchem-91 41 79     SPACE eurjchem-91 41 80 onto onto ADP eurjchem-91 41 81     SPACE eurjchem-91 41 82 ice ice NOUN eurjchem-91 41 83 / / SYM eurjchem-91 41 84 water water NOUN eurjchem-91 41 85 , , PUNCT eurjchem-91 41 86     SPACE eurjchem-91 41 87 the the DET eurjchem-91 41 88     SPACE eurjchem-91 41 89 precipitate precipitate NOUN eurjchem-91 41 90     SPACE eurjchem-91 41 91 so so ADV eurjchem-91 41 92     SPACE eurjchem-91 41 93 formed form VERB eurjchem-91 41 94     SPACE eurjchem-91 41 95 was be AUX eurjchem-91 41 96     SPACE eurjchem-91 41 97 filtered filter VERB eurjchem-91 41 98 , , PUNCT eurjchem-91 41 99     SPACE eurjchem-91 41 100 washed wash VERB eurjchem-91 41 101     SPACE eurjchem-91 41 102 several several ADJ eurjchem-91 41 103     SPACE eurjchem-91 41 104 times time NOUN eurjchem-91 41 105     SPACE eurjchem-91 41 106 with with ADP eurjchem-91 41 107     SPACE eurjchem-91 41 108 h2o h2o NOUN eurjchem-91 41 109     SPACE eurjchem-91 41 110 and and CCONJ eurjchem-91 41 111     SPACE eurjchem-91 41 112 crystallized crystallize VERB eurjchem-91 41 113     SPACE eurjchem-91 41 114 from from ADP eurjchem-91 41 115     SPACE eurjchem-91 41 116 acetic acetic ADJ eurjchem-91 41 117     SPACE eurjchem-91 41 118 acid acid NOUN eurjchem-91 41 119     SPACE eurjchem-91 41 120 to to PART eurjchem-91 41 121     SPACE eurjchem-91 41 122 give give VERB eurjchem-91 41 123     SPACE eurjchem-91 41 124 7 7 NUM eurjchem-91 41 125     SPACE eurjchem-91 41 126 as as ADV eurjchem-91 41 127     SPACE eurjchem-91 41 128 yellow yellow ADJ eurjchem-91 41 129     SPACE eurjchem-91 41 130 crystals crystal NOUN eurjchem-91 41 131 . . PUNCT eurjchem-91 41 132     SPACE eurjchem-91 42 1 m.p m.p PROPN eurjchem-91 42 2 . . PROPN eurjchem-91 42 3 : : PUNCT eurjchem-91 42 4     SPACE eurjchem-91 42 5 177 177 NUM eurjchem-91 42 6     SPACE eurjchem-91 42 7 ºc ºc PROPN eurjchem-91 42 8 . . PUNCT eurjchem-91 42 9     SPACE eurjchem-91 42 10 yield yield NOUN eurjchem-91 42 11 : : PUNCT eurjchem-91 42 12     SPACE eurjchem-91 42 13 0.28 0.28 NUM eurjchem-91 42 14     SPACE eurjchem-91 42 15 g g NOUN eurjchem-91 42 16 , , PUNCT eurjchem-91 42 17     SPACE eurjchem-91 42 18 68 68 NUM eurjchem-91 42 19 % % NOUN eurjchem-91 42 20     SPACE eurjchem-91 42 21 ( ( PUNCT eurjchem-91 42 22 scheme scheme NOUN eurjchem-91 42 23     SPACE eurjchem-91 42 24 3 3 NUM eurjchem-91 42 25 ) ) PUNCT eurjchem-91 42 26 . . PUNCT eurjchem-91 42 27         SPACE eurjchem-91 43 1 2.6.2 2.6.2 PROPN eurjchem-91 43 2 . . PUNCT eurjchem-91 43 3     SPACE eurjchem-91 43 4 method method VERB eurjchem-91 43 5     SPACE eurjchem-91 43 6 b b NOUN eurjchem-91 43 7         SPACE eurjchem-91 43 8 a a DET eurjchem-91 43 9     SPACE eurjchem-91 43 10 mixture mixture NOUN eurjchem-91 43 11     SPACE eurjchem-91 43 12 of of ADP eurjchem-91 43 13     SPACE eurjchem-91 43 14 compound compound NOUN eurjchem-91 43 15     SPACE eurjchem-91 43 16 1 1 NUM eurjchem-91 43 17     SPACE eurjchem-91 43 18 ( ( PUNCT eurjchem-91 43 19 0.514 0.514 NUM eurjchem-91 43 20     SPACE eurjchem-91 43 21 g g NOUN eurjchem-91 43 22 , , PUNCT eurjchem-91 43 23     SPACE eurjchem-91 43 24 2 2 NUM eurjchem-91 43 25     SPACE eurjchem-91 43 26 mmol mmol NOUN eurjchem-91 43 27 ) ) PUNCT eurjchem-91 43 28     SPACE eurjchem-91 43 29 and and CCONJ eurjchem-91 43 30     SPACE eurjchem-91 43 31 2‐hydroxy‐ 2‐hydroxy‐ NUM eurjchem-91 43 32 1‐naphthaldehyde 1‐naphthaldehyde NUM eurjchem-91 43 33     SPACE eurjchem-91 43 34 ( ( PUNCT eurjchem-91 43 35 0.34 0.34 NUM eurjchem-91 43 36     SPACE eurjchem-91 43 37 g g NOUN eurjchem-91 43 38 , , PUNCT eurjchem-91 43 39     SPACE eurjchem-91 43 40 2 2 NUM eurjchem-91 43 41     SPACE eurjchem-91 43 42 mmol mmol NOUN eurjchem-91 43 43 ) ) PUNCT eurjchem-91 43 44 , , PUNCT eurjchem-91 43 45     SPACE eurjchem-91 43 46 in in ADP eurjchem-91 43 47     SPACE eurjchem-91 43 48 glacial glacial ADJ eurjchem-91 43 49     SPACE eurjchem-91 43 50 acetic acetic ADJ eurjchem-91 43 51     SPACE eurjchem-91 43 52 acid acid NOUN eurjchem-91 43 53     SPACE eurjchem-91 43 54 ( ( PUNCT eurjchem-91 43 55 10 10 NUM eurjchem-91 43 56     SPACE eurjchem-91 43 57 ml ml NOUN eurjchem-91 43 58 ) ) PUNCT eurjchem-91 43 59     SPACE eurjchem-91 43 60 and and CCONJ eurjchem-91 43 61     SPACE eurjchem-91 43 62 freshly freshly ADV eurjchem-91 43 63     SPACE eurjchem-91 43 64 fused fuse VERB eurjchem-91 43 65     SPACE eurjchem-91 43 66 sodium sodium NOUN eurjchem-91 43 67     SPACE eurjchem-91 43 68 acetate acetate NOUN eurjchem-91 43 69     SPACE eurjchem-91 43 70 ( ( PUNCT eurjchem-91 43 71 0.2 0.2 NUM eurjchem-91 43 72     SPACE eurjchem-91 43 73 g g NOUN eurjchem-91 43 74 ) ) PUNCT eurjchem-91 43 75 , , PUNCT eurjchem-91 43 76     SPACE eurjchem-91 43 77 was be AUX eurjchem-91 43 78     SPACE eurjchem-91 43 79 heated heated ADJ eurjchem-91 43 80     SPACE eurjchem-91 43 81 under under ADP eurjchem-91 43 82     SPACE eurjchem-91 43 83 reflux reflux NOUN eurjchem-91 43 84     SPACE eurjchem-91 43 85 for for ADP eurjchem-91 43 86     SPACE eurjchem-91 43 87 4 4 NUM eurjchem-91 43 88     SPACE eurjchem-91 43 89 h. h. NOUN eurjchem-91 43 90     SPACE eurjchem-91 43 91 the the DET eurjchem-91 43 92     SPACE eurjchem-91 43 93 yellow yellow ADJ eurjchem-91 43 94     SPACE eurjchem-91 43 95 crystals crystal NOUN eurjchem-91 43 96     SPACE eurjchem-91 43 97 obtained obtain VERB eurjchem-91 43 98     SPACE eurjchem-91 43 99 after after SCONJ eurjchem-91 43 100     SPACE eurjchem-91 43 101 cooling cooling NOUN eurjchem-91 43 102     SPACE eurjchem-91 43 103 were be AUX eurjchem-91 43 104     SPACE eurjchem-91 43 105 filtered filter VERB eurjchem-91 43 106     SPACE eurjchem-91 43 107 and and CCONJ eurjchem-91 43 108     SPACE eurjchem-91 43 109 recrystallized recrystallize VERB eurjchem-91 43 110     SPACE eurjchem-91 43 111 from from ADP eurjchem-91 43 112     SPACE eurjchem-91 43 113 dmf dmf PROPN eurjchem-91 43 114     SPACE eurjchem-91 43 115 to to PART eurjchem-91 43 116     SPACE eurjchem-91 43 117 give give VERB eurjchem-91 43 118     SPACE eurjchem-91 43 119 7 7 NUM eurjchem-91 43 120     SPACE eurjchem-91 43 121 as as ADP eurjchem-91 43 122     SPACE eurjchem-91 43 123 white white ADJ eurjchem-91 43 124     SPACE eurjchem-91 43 125 crystals crystal NOUN eurjchem-91 43 126     SPACE eurjchem-91 43 127 ( ( PUNCT eurjchem-91 43 128 scheme scheme NOUN eurjchem-91 43 129     SPACE eurjchem-91 43 130 3 3 NUM eurjchem-91 43 131 ) ) PUNCT eurjchem-91 43 132 . . PUNCT eurjchem-91 43 133     SPACE eurjchem-91 44 1 m.p m.p PROPN eurjchem-91 44 2 . . PROPN eurjchem-91 44 3 : : PUNCT eurjchem-91 44 4     SPACE eurjchem-91 44 5 177 177 NUM eurjchem-91 44 6     SPACE eurjchem-91 44 7 ºc ºc PROPN eurjchem-91 44 8 . . PUNCT eurjchem-91 44 9     SPACE eurjchem-91 44 10 yield yield NOUN eurjchem-91 44 11 : : PUNCT eurjchem-91 44 12     SPACE eurjchem-91 44 13 0.46 0.46 NUM eurjchem-91 44 14     SPACE eurjchem-91 44 15 g g NOUN eurjchem-91 44 16 , , PUNCT eurjchem-91 44 17     SPACE eurjchem-91 44 18 56 56 NUM eurjchem-91 44 19 % % NOUN eurjchem-91 44 20 . . PUNCT eurjchem-91 44 21     SPACE eurjchem-91 45 1 ir ir VERB eurjchem-91 45 2     SPACE eurjchem-91 45 3 ( ( PUNCT eurjchem-91 45 4 kbr kbr PROPN eurjchem-91 45 5 , , PUNCT eurjchem-91 45 6     SPACE eurjchem-91 45 7 cm‐1 cm‐1 NOUN eurjchem-91 45 8 ): ): PUNCT eurjchem-91 45 9     SPACE eurjchem-91 45 10 3432 3432 NUM eurjchem-91 45 11     SPACE eurjchem-91 45 12 ( ( PUNCT eurjchem-91 45 13 oh oh INTJ eurjchem-91 45 14 ) ) PUNCT eurjchem-91 45 15 , , PUNCT eurjchem-91 45 16     SPACE eurjchem-91 45 17 3055 3055 NUM eurjchem-91 45 18     SPACE eurjchem-91 45 19 ( ( PUNCT eurjchem-91 45 20 charom charom NOUN eurjchem-91 45 21 . . PUNCT eurjchem-91 45 22 ) ) PUNCT eurjchem-91 45 23 , , PUNCT eurjchem-91 45 24     SPACE eurjchem-91 45 25 2976 2976 NUM eurjchem-91 45 26 , , PUNCT eurjchem-91 45 27     SPACE eurjchem-91 45 28 2927 2927 NUM eurjchem-91 45 29     SPACE eurjchem-91 45 30 ( ( PUNCT eurjchem-91 45 31 ch3 ch3 PROPN eurjchem-91 45 32 , , PUNCT eurjchem-91 45 33     SPACE eurjchem-91 45 34 ch2 ch2 PROPN eurjchem-91 45 35 ) ) PUNCT eurjchem-91 45 36 , , PUNCT eurjchem-91 45 37     SPACE eurjchem-91 45 38 1715 1715 NUM eurjchem-91 45 39     SPACE eurjchem-91 45 40 ( ( PUNCT eurjchem-91 45 41 oc oc PROPN eurjchem-91 45 42 = = NOUN eurjchem-91 45 43 o o NOUN eurjchem-91 45 44 ) ) PUNCT eurjchem-91 45 45 , , PUNCT eurjchem-91 45 46     SPACE eurjchem-91 45 47 1673 1673 NUM eurjchem-91 45 48     SPACE eurjchem-91 45 49 ( ( PUNCT eurjchem-91 45 50 c c NOUN eurjchem-91 45 51 = = NOUN eurjchem-91 45 52 oquinolinone oquinolinone NOUN eurjchem-91 45 53 ) ) PUNCT eurjchem-91 45 54 , , PUNCT eurjchem-91 45 55     SPACE eurjchem-91 45 56 1619 1619 NUM eurjchem-91 45 57     SPACE eurjchem-91 45 58 ( ( PUNCT eurjchem-91 45 59 c c NOUN eurjchem-91 45 60 = = NOUN eurjchem-91 45 61 oketone oketone NOUN eurjchem-91 45 62 ) ) PUNCT eurjchem-91 45 63 . . PUNCT eurjchem-91 45 64     SPACE eurjchem-91 45 65 1h 1h NUM eurjchem-91 45 66     SPACE eurjchem-91 45 67 nmr nmr NOUN eurjchem-91 45 68     SPACE eurjchem-91 45 69 ( ( PUNCT eurjchem-91 45 70 dmso‐d6 dmso‐d6 PROPN eurjchem-91 45 71 , , PUNCT eurjchem-91 45 72     SPACE eurjchem-91 45 73 δ δ PROPN eurjchem-91 45 74 ): ): PROPN eurjchem-91 45 75     SPACE eurjchem-91 45 76 1.24 1.24 NUM eurjchem-91 45 77     SPACE eurjchem-91 45 78 ( ( PUNCT eurjchem-91 45 79 t t PROPN eurjchem-91 45 80 , , PUNCT eurjchem-91 45 81     SPACE eurjchem-91 45 82 3h 3h NUM eurjchem-91 45 83 , , PUNCT eurjchem-91 45 84     SPACE eurjchem-91 45 85 j=7.4 j=7.4 NOUN eurjchem-91 45 86     SPACE eurjchem-91 45 87 hz hz VERB eurjchem-91 45 88 , , PUNCT eurjchem-91 45 89     SPACE eurjchem-91 45 90 ch3 ch3 PROPN eurjchem-91 45 91 ) ) PUNCT eurjchem-91 45 92 , , PUNCT eurjchem-91 45 93     SPACE eurjchem-91 45 94 4.36 4.36 NUM eurjchem-91 45 95     SPACE eurjchem-91 45 96 ( ( PUNCT eurjchem-91 45 97 q q NOUN eurjchem-91 45 98 , , PUNCT eurjchem-91 45 99     SPACE eurjchem-91 45 100 2h 2h NUM eurjchem-91 45 101 , , PUNCT eurjchem-91 45 102     SPACE eurjchem-91 45 103 j=7.4 j=7.4 NOUN eurjchem-91 45 104     SPACE eurjchem-91 45 105 hz hz VERB eurjchem-91 45 106 , , PUNCT eurjchem-91 45 107     SPACE eurjchem-91 45 108 ch2 ch2 PROPN eurjchem-91 45 109 ) ) PUNCT eurjchem-91 45 110 , , PUNCT eurjchem-91 45 111     SPACE eurjchem-91 45 112 7.48‐7.99 7.48‐7.99 NOUN eurjchem-91 45 113     SPACE eurjchem-91 45 114 ( ( PUNCT eurjchem-91 45 115 m m PROPN eurjchem-91 45 116 , , PUNCT eurjchem-91 45 117     SPACE eurjchem-91 45 118 10h 10h NUM eurjchem-91 45 119 , , PUNCT eurjchem-91 45 120     SPACE eurjchem-91 45 121 ar‐h ar‐h NOUN eurjchem-91 45 122 ) ) PUNCT eurjchem-91 45 123 , , PUNCT eurjchem-91 45 124     SPACE eurjchem-91 45 125 8.23 8.23 NUM eurjchem-91 45 126     SPACE eurjchem-91 45 127 ( ( PUNCT eurjchem-91 45 128 s s PROPN eurjchem-91 45 129 , , PUNCT eurjchem-91 45 130     SPACE eurjchem-91 45 131 1h 1h NUM eurjchem-91 45 132 , , PUNCT eurjchem-91 45 133     SPACE eurjchem-91 45 134 chmethine chmethine NOUN eurjchem-91 45 135 ) ) PUNCT eurjchem-91 45 136 , , PUNCT eurjchem-91 45 137     SPACE eurjchem-91 45 138 14.45 14.45 NUM eurjchem-91 45 139     SPACE eurjchem-91 45 140 ( ( PUNCT eurjchem-91 45 141 br br PROPN eurjchem-91 45 142 , , PUNCT eurjchem-91 45 143     SPACE eurjchem-91 45 144 1h 1h NUM eurjchem-91 45 145     SPACE eurjchem-91 45 146 exchangeable exchangeable ADJ eurjchem-91 45 147     SPACE eurjchem-91 45 148 with with ADP eurjchem-91 45 149     SPACE eurjchem-91 45 150 d2o d2o NOUN eurjchem-91 45 151 , , PUNCT eurjchem-91 45 152     SPACE eurjchem-91 45 153 ohnaphthalene ohnaphthalene NOUN eurjchem-91 45 154 ) ) PUNCT eurjchem-91 45 155 . . PUNCT eurjchem-91 45 156     SPACE eurjchem-91 46 1 anal anal ADJ eurjchem-91 46 2 . . PUNCT eurjchem-91 46 3     SPACE eurjchem-91 46 4 calcd calcd NOUN eurjchem-91 46 5     SPACE eurjchem-91 46 6 ( ( PUNCT eurjchem-91 46 7 c25h17no5 c25h17no5 PROPN eurjchem-91 46 8     SPACE eurjchem-91 46 9 ( ( PUNCT eurjchem-91 46 10 411.41 411.41 NUM eurjchem-91 46 11 ): ): PUNCT eurjchem-91 46 12     SPACE eurjchem-91 46 13 c c NOUN eurjchem-91 46 14 , , PUNCT eurjchem-91 46 15     SPACE eurjchem-91 46 16 72.99 72.99 NUM eurjchem-91 46 17 ; ; PUNCT eurjchem-91 46 18     SPACE eurjchem-91 46 19 h h NOUN eurjchem-91 46 20 , , PUNCT eurjchem-91 46 21     SPACE eurjchem-91 46 22 4.16 4.16 NUM eurjchem-91 46 23 ; ; PUNCT eurjchem-91 46 24     SPACE eurjchem-91 46 25 n n CCONJ eurjchem-91 46 26 , , PUNCT eurjchem-91 46 27     SPACE eurjchem-91 46 28 3.40 3.40 NUM eurjchem-91 46 29 % % NOUN eurjchem-91 46 30 . . PUNCT eurjchem-91 46 31     SPACE eurjchem-91 46 32 found find VERB eurjchem-91 46 33 : : PUNCT eurjchem-91 46 34     SPACE eurjchem-91 46 35 c c X eurjchem-91 46 36 , , PUNCT eurjchem-91 46 37     SPACE eurjchem-91 46 38 72.52 72.52 NUM eurjchem-91 46 39 ; ; PUNCT eurjchem-91 46 40     SPACE eurjchem-91 46 41 h h NOUN eurjchem-91 46 42 , , PUNCT eurjchem-91 46 43     SPACE eurjchem-91 46 44 4.08 4.08 NUM eurjchem-91 46 45 ; ; PUNCT eurjchem-91 46 46     SPACE eurjchem-91 46 47 n n CCONJ eurjchem-91 46 48 , , PUNCT eurjchem-91 46 49     SPACE eurjchem-91 46 50 3.28 3.28 NUM eurjchem-91 46 51 % % NOUN eurjchem-91 46 52 . . PUNCT eurjchem-91 46 53         SPACE eurjchem-91 47 1 ibrahim ibrahim PROPN eurjchem-91 47 2     SPACE eurjchem-91 47 3 et et PROPN eurjchem-91 47 4     SPACE eurjchem-91 47 5 al al PROPN eurjchem-91 47 6 . . PROPN eurjchem-91 47 7     SPACE eurjchem-91 47 8 / / SYM eurjchem-91 47 9     SPACE eurjchem-91 47 10 european european ADJ eurjchem-91 47 11     SPACE eurjchem-91 47 12 journal journal NOUN eurjchem-91 47 13     SPACE eurjchem-91 47 14 of of ADP eurjchem-91 47 15     SPACE eurjchem-91 47 16 chemistry chemistry NOUN eurjchem-91 47 17     SPACE eurjchem-91 47 18 1 1 NUM eurjchem-91 47 19     SPACE eurjchem-91 47 20 ( ( PUNCT eurjchem-91 47 21 3 3 NUM eurjchem-91 47 22 ) ) PUNCT eurjchem-91 47 23     SPACE eurjchem-91 47 24 ( ( PUNCT eurjchem-91 47 25 2010 2010 NUM eurjchem-91 47 26 ) ) PUNCT eurjchem-91 47 27     SPACE eurjchem-91 47 28 195­199 195­199 NUM eurjchem-91 47 29     SPACE eurjchem-91 47 30 197 197 NUM eurjchem-91 47 31     SPACE eurjchem-91 47 32 2.7 2.7 NUM eurjchem-91 47 33 . . PUNCT eurjchem-91 47 34     SPACE eurjchem-91 48 1 6­ethyl­3­(4­hydroxy­1­phenyl­2­oxo­1,2­dihydro­ 6­ethyl­3­(4­hydroxy­1­phenyl­2­oxo­1,2­dihydro­ NUM eurjchem-91 48 2 quinolin­3­yl)methylidene)2h­pyrano[3,2­c]quinoline­ quinolin­3­yl)methylidene)2h­pyrano[3,2­c]quinoline­ NOUN eurjchem-91 48 3 2,4,5(3h,6h)trione 2,4,5(3h,6h)trione NUM eurjchem-91 48 4     SPACE eurjchem-91 48 5 ( ( PUNCT eurjchem-91 48 6 10 10 NUM eurjchem-91 48 7 ) ) PUNCT eurjchem-91 48 8         SPACE eurjchem-91 48 9 a a DET eurjchem-91 48 10     SPACE eurjchem-91 48 11 mixture mixture NOUN eurjchem-91 48 12     SPACE eurjchem-91 48 13 of of ADP eurjchem-91 48 14     SPACE eurjchem-91 48 15 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 48 16     SPACE eurjchem-91 48 17 2 2 NUM eurjchem-91 48 18     SPACE eurjchem-91 48 19 ( ( PUNCT eurjchem-91 48 20 0.275 0.275 NUM eurjchem-91 48 21     SPACE eurjchem-91 48 22 g g NOUN eurjchem-91 48 23 , , PUNCT eurjchem-91 48 24     SPACE eurjchem-91 48 25 1 1 NUM eurjchem-91 48 26     SPACE eurjchem-91 48 27 mmol mmol NOUN eurjchem-91 48 28 ) ) PUNCT eurjchem-91 48 29     SPACE eurjchem-91 48 30 and and CCONJ eurjchem-91 48 31     SPACE eurjchem-91 48 32 4‐hydroxy‐ 4‐hydroxy‐ NUM eurjchem-91 48 33 2‐oxo‐1‐phenyl‐1,2‐dihydroquinoline‐3‐carboxaldehyde 2‐oxo‐1‐phenyl‐1,2‐dihydroquinoline‐3‐carboxaldehyde NUM eurjchem-91 48 34     SPACE eurjchem-91 48 35 ( ( PUNCT eurjchem-91 48 36 8) 8) NOUN eurjchem-91 48 37     SPACE eurjchem-91 48 38 ( ( PUNCT eurjchem-91 48 39 0.265 0.265 NOUN eurjchem-91 48 40     SPACE eurjchem-91 48 41 g g NOUN eurjchem-91 48 42 , , PUNCT eurjchem-91 48 43     SPACE eurjchem-91 48 44 1 1 NUM eurjchem-91 48 45     SPACE eurjchem-91 48 46 mmol mmol NOUN eurjchem-91 48 47 ) ) PUNCT eurjchem-91 48 48     SPACE eurjchem-91 48 49 in in ADP eurjchem-91 48 50     SPACE eurjchem-91 48 51 dmf dmf PROPN eurjchem-91 48 52     SPACE eurjchem-91 48 53 ( ( PUNCT eurjchem-91 48 54 5 5 NUM eurjchem-91 48 55     SPACE eurjchem-91 48 56 ml ml NOUN eurjchem-91 48 57 ) ) PUNCT eurjchem-91 48 58     SPACE eurjchem-91 48 59 containing contain VERB eurjchem-91 48 60     SPACE eurjchem-91 48 61 few few ADJ eurjchem-91 48 62     SPACE eurjchem-91 48 63 drops drop VERB eurjchem-91 48 64     SPACE eurjchem-91 48 65 of of ADP eurjchem-91 48 66     SPACE eurjchem-91 48 67 piperidine piperidine NOUN eurjchem-91 48 68     SPACE eurjchem-91 48 69 was be AUX eurjchem-91 48 70     SPACE eurjchem-91 48 71 heated heated ADJ eurjchem-91 48 72     SPACE eurjchem-91 48 73 at at ADP eurjchem-91 48 74     SPACE eurjchem-91 48 75 reflux reflux NOUN eurjchem-91 48 76     SPACE eurjchem-91 48 77 for for ADP eurjchem-91 48 78     SPACE eurjchem-91 48 79 2h 2h NUM eurjchem-91 48 80 . . PUNCT eurjchem-91 48 81     SPACE eurjchem-91 49 1 the the DET eurjchem-91 49 2     SPACE eurjchem-91 49 3 solid solid NOUN eurjchem-91 49 4     SPACE eurjchem-91 49 5 deposited deposit VERB eurjchem-91 49 6     SPACE eurjchem-91 49 7 after after SCONJ eurjchem-91 49 8     SPACE eurjchem-91 49 9 cooling cooling NOUN eurjchem-91 49 10     SPACE eurjchem-91 49 11 was be AUX eurjchem-91 49 12     SPACE eurjchem-91 49 13 filtered filter VERB eurjchem-91 49 14     SPACE eurjchem-91 49 15 and and CCONJ eurjchem-91 49 16     SPACE eurjchem-91 49 17 recrystallized recrystallize VERB eurjchem-91 49 18     SPACE eurjchem-91 49 19 from from ADP eurjchem-91 49 20     SPACE eurjchem-91 49 21 dmf dmf PROPN eurjchem-91 49 22     SPACE eurjchem-91 49 23 to to PART eurjchem-91 49 24     SPACE eurjchem-91 49 25 give give VERB eurjchem-91 49 26     SPACE eurjchem-91 49 27 10 10 NUM eurjchem-91 49 28     SPACE eurjchem-91 49 29 as as ADP eurjchem-91 49 30     SPACE eurjchem-91 49 31 yellow yellow ADJ eurjchem-91 49 32     SPACE eurjchem-91 49 33 crystals crystal NOUN eurjchem-91 49 34     SPACE eurjchem-91 49 35 ( ( PUNCT eurjchem-91 49 36 scheme scheme NOUN eurjchem-91 49 37     SPACE eurjchem-91 49 38 4 4 NUM eurjchem-91 49 39 ) ) PUNCT eurjchem-91 49 40 . . PUNCT eurjchem-91 49 41     SPACE eurjchem-91 50 1 m.p m.p PROPN eurjchem-91 50 2 . . PROPN eurjchem-91 50 3 : : PUNCT eurjchem-91 50 4     SPACE eurjchem-91 50 5 265 265 NUM eurjchem-91 50 6     SPACE eurjchem-91 50 7 ºc ºc PROPN eurjchem-91 50 8 . . PUNCT eurjchem-91 50 9     SPACE eurjchem-91 50 10 yield yield NOUN eurjchem-91 50 11 : : PUNCT eurjchem-91 50 12     SPACE eurjchem-91 50 13 0.21 0.21 NUM eurjchem-91 50 14     SPACE eurjchem-91 50 15 g g NOUN eurjchem-91 50 16 , , PUNCT eurjchem-91 50 17     SPACE eurjchem-91 50 18 42 42 NUM eurjchem-91 50 19 % % NOUN eurjchem-91 50 20 . . PUNCT eurjchem-91 50 21     SPACE eurjchem-91 51 1 ir ir VERB eurjchem-91 51 2     SPACE eurjchem-91 51 3 ( ( PUNCT eurjchem-91 51 4 kbr kbr PROPN eurjchem-91 51 5 , , PUNCT eurjchem-91 51 6     SPACE eurjchem-91 51 7 cm‐1 cm‐1 NOUN eurjchem-91 51 8 ): ): PUNCT eurjchem-91 51 9     SPACE eurjchem-91 51 10 3445 3445 NUM eurjchem-91 51 11     SPACE eurjchem-91 51 12 ( ( PUNCT eurjchem-91 51 13 oh oh INTJ eurjchem-91 51 14 ) ) PUNCT eurjchem-91 51 15 , , PUNCT eurjchem-91 51 16     SPACE eurjchem-91 51 17 3058 3058 NUM eurjchem-91 51 18     SPACE eurjchem-91 51 19 ( ( PUNCT eurjchem-91 51 20 charom charom NOUN eurjchem-91 51 21 . . PUNCT eurjchem-91 51 22 ) ) PUNCT eurjchem-91 51 23 , , PUNCT eurjchem-91 51 24     SPACE eurjchem-91 51 25 2934 2934 NUM eurjchem-91 51 26 , , PUNCT eurjchem-91 51 27     SPACE eurjchem-91 51 28 2859 2859 NUM eurjchem-91 51 29     SPACE eurjchem-91 51 30 ( ( PUNCT eurjchem-91 51 31 ch2 ch2 PROPN eurjchem-91 51 32 , , PUNCT eurjchem-91 51 33     SPACE eurjchem-91 51 34 ch3 ch3 PROPN eurjchem-91 51 35 ) ) PUNCT eurjchem-91 51 36 , , PUNCT eurjchem-91 51 37     SPACE eurjchem-91 51 38 1746 1746 NUM eurjchem-91 51 39     SPACE eurjchem-91 51 40 ( ( PUNCT eurjchem-91 51 41 oc oc PROPN eurjchem-91 51 42 = = NOUN eurjchem-91 51 43 o o NOUN eurjchem-91 51 44 ) ) PUNCT eurjchem-91 51 45 , , PUNCT eurjchem-91 51 46     SPACE eurjchem-91 51 47 1661 1661 NUM eurjchem-91 51 48     SPACE eurjchem-91 51 49 ( ( PUNCT eurjchem-91 51 50 2c 2c NOUN eurjchem-91 51 51 = = NOUN eurjchem-91 51 52 oquinolinone oquinolinone NOUN eurjchem-91 51 53 ) ) PUNCT eurjchem-91 51 54 , , PUNCT eurjchem-91 51 55     SPACE eurjchem-91 51 56 1636 1636 NUM eurjchem-91 51 57     SPACE eurjchem-91 51 58 ( ( PUNCT eurjchem-91 51 59 c c NOUN eurjchem-91 51 60 = = NOUN eurjchem-91 51 61 oketone oketone NOUN eurjchem-91 51 62 ) ) PUNCT eurjchem-91 51 63 . . PUNCT eurjchem-91 51 64     SPACE eurjchem-91 51 65 1h 1h NUM eurjchem-91 51 66     SPACE eurjchem-91 51 67 nmr nmr NOUN eurjchem-91 51 68     SPACE eurjchem-91 51 69 ( ( PUNCT eurjchem-91 51 70 dmso‐d6 dmso‐d6 PROPN eurjchem-91 51 71 , , PUNCT eurjchem-91 51 72     SPACE eurjchem-91 51 73 δ δ PROPN eurjchem-91 51 74 ): ): PUNCT eurjchem-91 51 75     SPACE eurjchem-91 51 76 1.22 1.22 NUM eurjchem-91 51 77     SPACE eurjchem-91 51 78 ( ( PUNCT eurjchem-91 51 79 t t PROPN eurjchem-91 51 80 , , PUNCT eurjchem-91 51 81     SPACE eurjchem-91 51 82 3h 3h NUM eurjchem-91 51 83 , , PUNCT eurjchem-91 51 84     SPACE eurjchem-91 51 85 ch3 ch3 PROPN eurjchem-91 51 86 ) ) PUNCT eurjchem-91 51 87 , , PUNCT eurjchem-91 51 88     SPACE eurjchem-91 51 89 4.34 4.34 NUM eurjchem-91 51 90     SPACE eurjchem-91 51 91 ( ( PUNCT eurjchem-91 51 92 q q NOUN eurjchem-91 51 93 , , PUNCT eurjchem-91 51 94     SPACE eurjchem-91 51 95 2h 2h NUM eurjchem-91 51 96 , , PUNCT eurjchem-91 51 97     SPACE eurjchem-91 51 98 ch2 ch2 NOUN eurjchem-91 51 99 ) ) PUNCT eurjchem-91 51 100 , , PUNCT eurjchem-91 51 101     SPACE eurjchem-91 51 102 6.61‐6.64 6.61‐6.64 NOUN eurjchem-91 51 103     SPACE eurjchem-91 51 104 ( ( PUNCT eurjchem-91 51 105 m m PROPN eurjchem-91 51 106 , , PUNCT eurjchem-91 51 107     SPACE eurjchem-91 51 108 2h 2h NUM eurjchem-91 51 109 , , PUNCT eurjchem-91 51 110     SPACE eurjchem-91 51 111 ar‐h ar‐h NOUN eurjchem-91 51 112 ) ) PUNCT eurjchem-91 51 113 , , PUNCT eurjchem-91 51 114     SPACE eurjchem-91 51 115 7.35‐7.45 7.35‐7.45 NUM eurjchem-91 51 116     SPACE eurjchem-91 51 117 ( ( PUNCT eurjchem-91 51 118 m m PROPN eurjchem-91 51 119 , , PUNCT eurjchem-91 51 120     SPACE eurjchem-91 51 121 4h 4h NOUN eurjchem-91 51 122 , , PUNCT eurjchem-91 51 123     SPACE eurjchem-91 51 124 ar‐h ar‐h NOUN eurjchem-91 51 125 ) ) PUNCT eurjchem-91 51 126 , , PUNCT eurjchem-91 51 127     SPACE eurjchem-91 51 128 7.59‐7.65 7.59‐7.65 NUM eurjchem-91 51 129     SPACE eurjchem-91 51 130 ( ( PUNCT eurjchem-91 51 131 m m PROPN eurjchem-91 51 132 , , PUNCT eurjchem-91 51 133     SPACE eurjchem-91 51 134 5h 5h NUM eurjchem-91 51 135 , , PUNCT eurjchem-91 51 136     SPACE eurjchem-91 51 137 ar‐h ar‐h NOUN eurjchem-91 51 138 ) ) PUNCT eurjchem-91 51 139 , , PUNCT eurjchem-91 51 140     SPACE eurjchem-91 51 141 8.05 8.05 NUM eurjchem-91 51 142     SPACE eurjchem-91 51 143 ( ( PUNCT eurjchem-91 51 144 s s PROPN eurjchem-91 51 145 , , PUNCT eurjchem-91 51 146     SPACE eurjchem-91 51 147 1h 1h NUM eurjchem-91 51 148 , , PUNCT eurjchem-91 51 149     SPACE eurjchem-91 51 150 chmethine chmethine NOUN eurjchem-91 51 151 ) ) PUNCT eurjchem-91 51 152 , , PUNCT eurjchem-91 51 153     SPACE eurjchem-91 51 154 8.09‐8.14 8.09‐8.14 NUM eurjchem-91 51 155     SPACE eurjchem-91 51 156 ( ( PUNCT eurjchem-91 51 157 m m PROPN eurjchem-91 51 158 , , PUNCT eurjchem-91 51 159     SPACE eurjchem-91 51 160 2h 2h NUM eurjchem-91 51 161 , , PUNCT eurjchem-91 51 162     SPACE eurjchem-91 51 163 ar‐h ar‐h NOUN eurjchem-91 51 164 ) ) PUNCT eurjchem-91 51 165 . . PUNCT eurjchem-91 51 166     SPACE eurjchem-91 51 167 13c 13c NOUN eurjchem-91 51 168     SPACE eurjchem-91 51 169 nmr nmr NOUN eurjchem-91 51 170     SPACE eurjchem-91 51 171 ( ( PUNCT eurjchem-91 51 172 dmso‐ dmso‐ PROPN eurjchem-91 51 173 d6 d6 NOUN eurjchem-91 51 174 , , PUNCT eurjchem-91 51 175     SPACE eurjchem-91 51 176 δ δ PROPN eurjchem-91 51 177 ): ): PUNCT eurjchem-91 51 178     SPACE eurjchem-91 51 179 14.2 14.2 NUM eurjchem-91 51 180     SPACE eurjchem-91 51 181 ( ( PUNCT eurjchem-91 51 182 ch3 ch3 PROPN eurjchem-91 51 183 ) ) PUNCT eurjchem-91 51 184 , , PUNCT eurjchem-91 51 185     SPACE eurjchem-91 51 186 42.3 42.3 NUM eurjchem-91 51 187     SPACE eurjchem-91 51 188 ( ( PUNCT eurjchem-91 51 189 ch2 ch2 PROPN eurjchem-91 51 190 ) ) PUNCT eurjchem-91 51 191 , , PUNCT eurjchem-91 51 192     SPACE eurjchem-91 51 193 110.2 110.2 NUM eurjchem-91 51 194 , , PUNCT eurjchem-91 51 195     SPACE eurjchem-91 51 196 113.7 113.7 NUM eurjchem-91 51 197 , , PUNCT eurjchem-91 51 198     SPACE eurjchem-91 51 199 115.1 115.1 NUM eurjchem-91 51 200 , , PUNCT eurjchem-91 51 201     SPACE eurjchem-91 51 202 115.6 115.6 NUM eurjchem-91 51 203 , , PUNCT eurjchem-91 51 204     SPACE eurjchem-91 51 205 115.7 115.7 NUM eurjchem-91 51 206 , , PUNCT eurjchem-91 51 207     SPACE eurjchem-91 51 208 116.2 116.2 NUM eurjchem-91 51 209 , , PUNCT eurjchem-91 51 210     SPACE eurjchem-91 51 211 118.6 118.6 NUM eurjchem-91 51 212 , , PUNCT eurjchem-91 51 213     SPACE eurjchem-91 51 214 118.8 118.8 NUM eurjchem-91 51 215 , , PUNCT eurjchem-91 51 216     SPACE eurjchem-91 51 217 120.5 120.5 NUM eurjchem-91 51 218 , , PUNCT eurjchem-91 51 219     SPACE eurjchem-91 51 220 120.9 120.9 NUM eurjchem-91 51 221 , , PUNCT eurjchem-91 51 222     SPACE eurjchem-91 51 223 127.0 127.0 NUM eurjchem-91 51 224 , , PUNCT eurjchem-91 51 225     SPACE eurjchem-91 51 226 129.6 129.6 NUM eurjchem-91 51 227 , , PUNCT eurjchem-91 51 228     SPACE eurjchem-91 51 229 130.2 130.2 NUM eurjchem-91 51 230 , , PUNCT eurjchem-91 51 231     SPACE eurjchem-91 51 232 130.3 130.3 NUM eurjchem-91 51 233 , , PUNCT eurjchem-91 51 234     SPACE eurjchem-91 51 235 130.6 130.6 NUM eurjchem-91 51 236 , , PUNCT eurjchem-91 51 237     SPACE eurjchem-91 51 238 131.7 131.7 NUM eurjchem-91 51 239 , , PUNCT eurjchem-91 51 240     SPACE eurjchem-91 51 241 136.0 136.0 NUM eurjchem-91 51 242 , , PUNCT eurjchem-91 51 243     SPACE eurjchem-91 51 244 139.5 139.5 NUM eurjchem-91 51 245 , , PUNCT eurjchem-91 51 246     SPACE eurjchem-91 51 247 143.5 143.5 NUM eurjchem-91 51 248     SPACE eurjchem-91 51 249 ( ( PUNCT eurjchem-91 51 250 chmethine chmethine PROPN eurjchem-91 51 251 ) ) PUNCT eurjchem-91 51 252 , , PUNCT eurjchem-91 51 253     SPACE eurjchem-91 51 254 153.4 153.4 NUM eurjchem-91 51 255 , , PUNCT eurjchem-91 51 256     SPACE eurjchem-91 51 257 154.7 154.7 NUM eurjchem-91 51 258 , , PUNCT eurjchem-91 51 259     SPACE eurjchem-91 51 260 163.0 163.0 NUM eurjchem-91 51 261     SPACE eurjchem-91 51 262 ( ( PUNCT eurjchem-91 51 263 c2 c2 PROPN eurjchem-91 51 264 ` ` PUNCT eurjchem-91 51 265     SPACE eurjchem-91 51 266 as as ADP eurjchem-91 51 267     SPACE eurjchem-91 51 268 c c NOUN eurjchem-91 51 269 = = NOUN eurjchem-91 51 270 o o NOUN eurjchem-91 51 271 ) ) PUNCT eurjchem-91 51 272 , , PUNCT eurjchem-91 51 273     SPACE eurjchem-91 51 274 165.3 165.3 NUM eurjchem-91 51 275     SPACE eurjchem-91 51 276 ( ( PUNCT eurjchem-91 51 277 c5 c5 PROPN eurjchem-91 51 278     SPACE eurjchem-91 51 279 as as ADP eurjchem-91 51 280     SPACE eurjchem-91 51 281 c c NOUN eurjchem-91 51 282 = = NOUN eurjchem-91 51 283 o o NOUN eurjchem-91 51 284 ) ) PUNCT eurjchem-91 51 285 , , PUNCT eurjchem-91 51 286     SPACE eurjchem-91 51 287 167.9 167.9 NUM eurjchem-91 51 288     SPACE eurjchem-91 51 289 ( ( PUNCT eurjchem-91 51 290 c2 c2 PROPN eurjchem-91 51 291     SPACE eurjchem-91 51 292 as as ADP eurjchem-91 51 293     SPACE eurjchem-91 51 294 c c NOUN eurjchem-91 51 295 = = NOUN eurjchem-91 51 296 o o NOUN eurjchem-91 51 297 ) ) PUNCT eurjchem-91 51 298 , , PUNCT eurjchem-91 51 299     SPACE eurjchem-91 51 300 194.5 194.5 NUM eurjchem-91 51 301     SPACE eurjchem-91 51 302 ( ( PUNCT eurjchem-91 51 303 c4 c4 NOUN eurjchem-91 51 304     SPACE eurjchem-91 51 305 as as ADP eurjchem-91 51 306     SPACE eurjchem-91 51 307 c c NOUN eurjchem-91 51 308 = = NOUN eurjchem-91 51 309 o o NOUN eurjchem-91 51 310 ) ) PUNCT eurjchem-91 51 311 . . PUNCT eurjchem-91 51 312     SPACE eurjchem-91 52 1 anal anal ADJ eurjchem-91 52 2 . . PUNCT eurjchem-91 52 3     SPACE eurjchem-91 52 4 calcd calcd NOUN eurjchem-91 52 5     SPACE eurjchem-91 52 6 for for ADP eurjchem-91 52 7     SPACE eurjchem-91 52 8 c30h20n2o6 c30h20n2o6 PROPN eurjchem-91 52 9     SPACE eurjchem-91 52 10 ( ( PUNCT eurjchem-91 52 11 504.49 504.49 NUM eurjchem-91 52 12 ): ): PUNCT eurjchem-91 52 13     SPACE eurjchem-91 52 14 c c NOUN eurjchem-91 52 15 , , PUNCT eurjchem-91 52 16     SPACE eurjchem-91 52 17 71.36 71.36 NUM eurjchem-91 52 18 ; ; PUNCT eurjchem-91 52 19     SPACE eurjchem-91 52 20 h h NOUN eurjchem-91 52 21 , , PUNCT eurjchem-91 52 22     SPACE eurjchem-91 52 23 3.96 3.96 NUM eurjchem-91 52 24 , , PUNCT eurjchem-91 52 25     SPACE eurjchem-91 52 26 n n CCONJ eurjchem-91 52 27 , , PUNCT eurjchem-91 52 28     SPACE eurjchem-91 52 29 5.55 5.55 NUM eurjchem-91 52 30 % % NOUN eurjchem-91 52 31 . . PUNCT eurjchem-91 52 32     SPACE eurjchem-91 52 33 found find VERB eurjchem-91 52 34 : : PUNCT eurjchem-91 52 35     SPACE eurjchem-91 52 36 c c X eurjchem-91 52 37 , , PUNCT eurjchem-91 52 38     SPACE eurjchem-91 52 39 71.32 71.32 NUM eurjchem-91 52 40 ; ; PUNCT eurjchem-91 52 41     SPACE eurjchem-91 52 42 h h NOUN eurjchem-91 52 43 , , PUNCT eurjchem-91 52 44     SPACE eurjchem-91 52 45 3.87 3.87 NUM eurjchem-91 52 46 ; ; PUNCT eurjchem-91 52 47     SPACE eurjchem-91 52 48 n n CCONJ eurjchem-91 52 49 , , PUNCT eurjchem-91 52 50     SPACE eurjchem-91 52 51 5.90 5.90 NUM eurjchem-91 52 52 % % NOUN eurjchem-91 52 53 . . PUNCT eurjchem-91 52 54         SPACE eurjchem-91 53 1 n n PRON eurjchem-91 53 2 o o NOUN eurjchem-91 53 3 oh oh INTJ eurjchem-91 53 4 ph ph PROPN eurjchem-91 53 5 cho cho NOUN eurjchem-91 53 6 2 2 NUM eurjchem-91 53 7 dmf/ dmf/ PROPN eurjchem-91 53 8 pip pip NOUN eurjchem-91 53 9 . . PUNCT eurjchem-91 54 1 o o X eurjchem-91 55 1 o o X eurjchem-91 55 2 o o NOUN eurjchem-91 55 3 n n CCONJ eurjchem-91 55 4 o o NOUN eurjchem-91 55 5 n n ADP eurjchem-91 55 6 o o X eurjchem-91 55 7 et et NOUN eurjchem-91 55 8 ho ho PROPN eurjchem-91 55 9 ph ph PROPN eurjchem-91 55 10 8 8 NUM eurjchem-91 55 11 n n NUM eurjchem-91 55 12 n n NOUN eurjchem-91 55 13 o o NOUN eurjchem-91 56 1 oh oh INTJ eurjchem-91 56 2 cho cho NOUN eurjchem-91 57 1 9 9 NUM eurjchem-91 57 2 o o NOUN eurjchem-91 58 1 o o X eurjchem-91 59 1 o o NOUN eurjchem-91 60 1 n n CCONJ eurjchem-91 61 1 n n ADV eurjchem-91 62 1 oh oh INTJ eurjchem-91 62 2 n n CCONJ eurjchem-91 62 3 o o INTJ eurjchem-91 62 4 et et NOUN eurjchem-91 62 5 o o NOUN eurjchem-91 62 6 11 11 NUM eurjchem-91 62 7 dmf/ dmf/ PROPN eurjchem-91 62 8 pip pip NOUN eurjchem-91 62 9 . . PUNCT eurjchem-91 63 1 10 10 NUM eurjchem-91 63 2 42%47 42%47 NUM eurjchem-91 63 3 % % NOUN eurjchem-91 63 4 scheme scheme NOUN eurjchem-91 63 5     SPACE eurjchem-91 63 6 4 4 NUM eurjchem-91 63 7         SPACE eurjchem-91 63 8 2.8 2.8 NUM eurjchem-91 63 9 . . PUNCT eurjchem-91 63 10     SPACE eurjchem-91 64 1 6­ethyl­3­[(2­hydroxy­4­oxo­4h­pyrido[1,2­a]pyrimidin­ 6­ethyl­3­[(2­hydroxy­4­oxo­4h­pyrido[1,2­a]pyrimidin­ NUM eurjchem-91 64 2 3­yl)methylidene]­2h­pyrano[3,2­c]quinoline­2,4,5(3h,6h)­ 3­yl)methylidene]­2h­pyrano[3,2­c]quinoline­2,4,5(3h,6h)­ NUM eurjchem-91 64 3 trione trione NOUN eurjchem-91 64 4     SPACE eurjchem-91 64 5 ( ( PUNCT eurjchem-91 64 6 11 11 NUM eurjchem-91 64 7 ) ) PUNCT eurjchem-91 64 8         SPACE eurjchem-91 64 9 a a DET eurjchem-91 64 10     SPACE eurjchem-91 64 11 mixture mixture NOUN eurjchem-91 64 12     SPACE eurjchem-91 64 13 of of ADP eurjchem-91 64 14     SPACE eurjchem-91 64 15 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 64 16     SPACE eurjchem-91 64 17 2 2 NUM eurjchem-91 64 18     SPACE eurjchem-91 64 19 ( ( PUNCT eurjchem-91 64 20 0.275 0.275 NUM eurjchem-91 64 21     SPACE eurjchem-91 64 22 g g NOUN eurjchem-91 64 23 , , PUNCT eurjchem-91 64 24     SPACE eurjchem-91 64 25 1 1 NUM eurjchem-91 64 26     SPACE eurjchem-91 64 27 mmol mmol NOUN eurjchem-91 64 28 ) ) PUNCT eurjchem-91 64 29     SPACE eurjchem-91 64 30 and and CCONJ eurjchem-91 64 31     SPACE eurjchem-91 64 32 2‐hydroxy‐ 2‐hydroxy‐ NUM eurjchem-91 64 33 4‐oxo‐4h‐pyrido[1,2‐a]pyrimidine‐3‐carboxaldehyde 4‐oxo‐4h‐pyrido[1,2‐a]pyrimidine‐3‐carboxaldehyde NUM eurjchem-91 64 34     SPACE eurjchem-91 64 35 ( ( PUNCT eurjchem-91 64 36 9 9 NUM eurjchem-91 64 37 ) ) PUNCT eurjchem-91 64 38     SPACE eurjchem-91 64 39 ( ( PUNCT eurjchem-91 64 40 0.19 0.19 NUM eurjchem-91 64 41     SPACE eurjchem-91 64 42 g g NOUN eurjchem-91 64 43 , , PUNCT eurjchem-91 64 44     SPACE eurjchem-91 64 45 1 1 NUM eurjchem-91 64 46     SPACE eurjchem-91 64 47 mmol mmol NOUN eurjchem-91 64 48 ) ) PUNCT eurjchem-91 64 49     SPACE eurjchem-91 64 50 in in ADP eurjchem-91 64 51     SPACE eurjchem-91 64 52 dmf dmf PROPN eurjchem-91 64 53     SPACE eurjchem-91 64 54 ( ( PUNCT eurjchem-91 64 55 5 5 NUM eurjchem-91 64 56     SPACE eurjchem-91 64 57 ml ml NOUN eurjchem-91 64 58 ) ) PUNCT eurjchem-91 64 59     SPACE eurjchem-91 64 60 containing contain VERB eurjchem-91 64 61     SPACE eurjchem-91 64 62 few few ADJ eurjchem-91 64 63     SPACE eurjchem-91 64 64 drops drop VERB eurjchem-91 64 65     SPACE eurjchem-91 64 66 of of ADP eurjchem-91 64 67     SPACE eurjchem-91 64 68 piperidine piperidine NOUN eurjchem-91 64 69     SPACE eurjchem-91 64 70 was be AUX eurjchem-91 64 71     SPACE eurjchem-91 64 72 heated heated ADJ eurjchem-91 64 73     SPACE eurjchem-91 64 74 at at ADP eurjchem-91 64 75     SPACE eurjchem-91 64 76 reflux reflux NOUN eurjchem-91 64 77     SPACE eurjchem-91 64 78 for for ADP eurjchem-91 64 79     SPACE eurjchem-91 64 80 2h 2h NUM eurjchem-91 64 81 . . PUNCT eurjchem-91 64 82     SPACE eurjchem-91 65 1 the the DET eurjchem-91 65 2     SPACE eurjchem-91 65 3 solid solid NOUN eurjchem-91 65 4     SPACE eurjchem-91 65 5 deposited deposit VERB eurjchem-91 65 6     SPACE eurjchem-91 65 7 after after ADP eurjchem-91 65 8     SPACE eurjchem-91 65 9 cooling cooling NOUN eurjchem-91 65 10     SPACE eurjchem-91 65 11 was be AUX eurjchem-91 65 12     SPACE eurjchem-91 65 13 filtered filter VERB eurjchem-91 65 14     SPACE eurjchem-91 65 15 and and CCONJ eurjchem-91 65 16     SPACE eurjchem-91 65 17 recrystallized recrystallize VERB eurjchem-91 65 18     SPACE eurjchem-91 65 19 from from ADP eurjchem-91 65 20     SPACE eurjchem-91 65 21 dmf dmf PROPN eurjchem-91 65 22     SPACE eurjchem-91 65 23 to to PART eurjchem-91 65 24     SPACE eurjchem-91 65 25 give give VERB eurjchem-91 65 26     SPACE eurjchem-91 65 27 11 11 NUM eurjchem-91 65 28     SPACE eurjchem-91 65 29 as as ADP eurjchem-91 65 30     SPACE eurjchem-91 65 31 orange orange ADJ eurjchem-91 65 32     SPACE eurjchem-91 65 33 crystals crystal NOUN eurjchem-91 65 34     SPACE eurjchem-91 65 35 ( ( PUNCT eurjchem-91 65 36 scheme scheme NOUN eurjchem-91 65 37     SPACE eurjchem-91 65 38 4 4 NUM eurjchem-91 65 39 ) ) PUNCT eurjchem-91 65 40 . . PUNCT eurjchem-91 65 41     SPACE eurjchem-91 66 1 m.p m.p PROPN eurjchem-91 66 2 . . PROPN eurjchem-91 66 3 : : PUNCT eurjchem-91 66 4     SPACE eurjchem-91 66 5 215 215 NUM eurjchem-91 66 6     SPACE eurjchem-91 66 7 ºc ºc PROPN eurjchem-91 66 8 . . PUNCT eurjchem-91 66 9     SPACE eurjchem-91 66 10 yield yield NOUN eurjchem-91 66 11 : : PUNCT eurjchem-91 66 12     SPACE eurjchem-91 66 13 0.20 0.20 NUM eurjchem-91 66 14     SPACE eurjchem-91 66 15 g g NOUN eurjchem-91 66 16 , , PUNCT eurjchem-91 66 17     SPACE eurjchem-91 66 18 47 47 NUM eurjchem-91 66 19 % % NOUN eurjchem-91 66 20 . . PUNCT eurjchem-91 66 21     SPACE eurjchem-91 67 1 ir ir VERB eurjchem-91 67 2     SPACE eurjchem-91 67 3 ( ( PUNCT eurjchem-91 67 4 kbr kbr PROPN eurjchem-91 67 5 , , PUNCT eurjchem-91 67 6     SPACE eurjchem-91 67 7 cm‐1 cm‐1 NOUN eurjchem-91 67 8 ): ): PUNCT eurjchem-91 67 9     SPACE eurjchem-91 67 10 3407 3407 NUM eurjchem-91 67 11     SPACE eurjchem-91 67 12 ( ( PUNCT eurjchem-91 67 13 oh oh INTJ eurjchem-91 67 14 ) ) PUNCT eurjchem-91 67 15 , , PUNCT eurjchem-91 67 16     SPACE eurjchem-91 67 17 3060 3060 NUM eurjchem-91 67 18     SPACE eurjchem-91 67 19 ( ( PUNCT eurjchem-91 67 20 charom charom NOUN eurjchem-91 67 21 . . PUNCT eurjchem-91 67 22 ) ) PUNCT eurjchem-91 67 23 , , PUNCT eurjchem-91 67 24     SPACE eurjchem-91 67 25 2978 2978 NUM eurjchem-91 67 26 , , PUNCT eurjchem-91 67 27     SPACE eurjchem-91 67 28 2927 2927 NUM eurjchem-91 67 29     SPACE eurjchem-91 67 30 ( ( PUNCT eurjchem-91 67 31 ch2 ch2 PROPN eurjchem-91 67 32 , , PUNCT eurjchem-91 67 33     SPACE eurjchem-91 67 34 ch3 ch3 PROPN eurjchem-91 67 35 ) ) PUNCT eurjchem-91 67 36 , , PUNCT eurjchem-91 67 37     SPACE eurjchem-91 67 38 1732 1732 NUM eurjchem-91 67 39     SPACE eurjchem-91 67 40 ( ( PUNCT eurjchem-91 67 41 oc oc PROPN eurjchem-91 67 42 = = NOUN eurjchem-91 67 43 o o NOUN eurjchem-91 67 44 ) ) PUNCT eurjchem-91 67 45 , , PUNCT eurjchem-91 67 46     SPACE eurjchem-91 67 47 1671 1671 NUM eurjchem-91 67 48     SPACE eurjchem-91 67 49 ( ( PUNCT eurjchem-91 67 50 2c 2c NOUN eurjchem-91 67 51 = = SYM eurjchem-91 67 52 o o NOUN eurjchem-91 67 53 ) ) PUNCT eurjchem-91 67 54 , , PUNCT eurjchem-91 67 55     SPACE eurjchem-91 67 56 1623 1623 NUM eurjchem-91 67 57     SPACE eurjchem-91 67 58 ( ( PUNCT eurjchem-91 67 59 c c NOUN eurjchem-91 67 60 = = NOUN eurjchem-91 67 61 oketone oketone NOUN eurjchem-91 67 62 ) ) PUNCT eurjchem-91 67 63 . . PUNCT eurjchem-91 67 64     SPACE eurjchem-91 67 65 1h 1h NUM eurjchem-91 67 66     SPACE eurjchem-91 67 67 nmr nmr NOUN eurjchem-91 67 68     SPACE eurjchem-91 67 69 ( ( PUNCT eurjchem-91 67 70 dmso‐d6 dmso‐d6 PROPN eurjchem-91 67 71 , , PUNCT eurjchem-91 67 72     SPACE eurjchem-91 67 73 δ δ PROPN eurjchem-91 67 74 ): ): PUNCT eurjchem-91 67 75     SPACE eurjchem-91 67 76 1.29 1.29 NUM eurjchem-91 67 77     SPACE eurjchem-91 67 78 ( ( PUNCT eurjchem-91 67 79 t t PROPN eurjchem-91 67 80 , , PUNCT eurjchem-91 67 81     SPACE eurjchem-91 67 82 3h 3h NUM eurjchem-91 67 83 , , PUNCT eurjchem-91 67 84     SPACE eurjchem-91 67 85 j=7 j=7 NOUN eurjchem-91 67 86     SPACE eurjchem-91 67 87 hz hz VERB eurjchem-91 67 88 , , PUNCT eurjchem-91 67 89     SPACE eurjchem-91 67 90 ch3 ch3 PROPN eurjchem-91 67 91 ) ) PUNCT eurjchem-91 67 92 , , PUNCT eurjchem-91 67 93     SPACE eurjchem-91 67 94 4.39 4.39 NUM eurjchem-91 67 95     SPACE eurjchem-91 67 96 ( ( PUNCT eurjchem-91 67 97 q q NOUN eurjchem-91 67 98 , , PUNCT eurjchem-91 67 99     SPACE eurjchem-91 67 100 2h 2h NUM eurjchem-91 67 101 , , PUNCT eurjchem-91 67 102     SPACE eurjchem-91 67 103 j=7 j=7 NOUN eurjchem-91 67 104     SPACE eurjchem-91 67 105 hz hz VERB eurjchem-91 67 106 , , PUNCT eurjchem-91 67 107     SPACE eurjchem-91 67 108 ch2 ch2 PROPN eurjchem-91 67 109 ) ) PUNCT eurjchem-91 67 110 , , PUNCT eurjchem-91 67 111     SPACE eurjchem-91 67 112 7.30‐7.92 7.30‐7.92 NUM eurjchem-91 67 113     SPACE eurjchem-91 67 114 ( ( PUNCT eurjchem-91 67 115 m m PROPN eurjchem-91 67 116 , , PUNCT eurjchem-91 67 117     SPACE eurjchem-91 67 118 7h 7h NUM eurjchem-91 67 119 , , PUNCT eurjchem-91 67 120     SPACE eurjchem-91 67 121 ar‐h ar‐h NOUN eurjchem-91 67 122 ) ) PUNCT eurjchem-91 67 123 , , PUNCT eurjchem-91 67 124     SPACE eurjchem-91 67 125 8.02 8.02 NUM eurjchem-91 67 126     SPACE eurjchem-91 67 127 ( ( PUNCT eurjchem-91 67 128 s s PROPN eurjchem-91 67 129 , , PUNCT eurjchem-91 67 130     SPACE eurjchem-91 67 131 1h 1h NUM eurjchem-91 67 132 , , PUNCT eurjchem-91 67 133     SPACE eurjchem-91 67 134 chmethine chmethine NOUN eurjchem-91 67 135 ) ) PUNCT eurjchem-91 67 136 , , PUNCT eurjchem-91 67 137     SPACE eurjchem-91 67 138 8.08 8.08 NUM eurjchem-91 67 139     SPACE eurjchem-91 67 140 ( ( PUNCT eurjchem-91 67 141 d d PROPN eurjchem-91 67 142 , , PUNCT eurjchem-91 67 143     SPACE eurjchem-91 67 144 1h 1h NUM eurjchem-91 67 145 , , PUNCT eurjchem-91 67 146     SPACE eurjchem-91 67 147 j=7.2 j=7.2 NOUN eurjchem-91 67 148     SPACE eurjchem-91 67 149 hz hz VERB eurjchem-91 67 150 , , PUNCT eurjchem-91 67 151     SPACE eurjchem-91 67 152 ar‐h ar‐h NOUN eurjchem-91 67 153 ) ) PUNCT eurjchem-91 67 154 , , PUNCT eurjchem-91 67 155     SPACE eurjchem-91 67 156 14.14 14.14 NUM eurjchem-91 67 157     SPACE eurjchem-91 67 158 ( ( PUNCT eurjchem-91 67 159 bs bs PROPN eurjchem-91 67 160 , , PUNCT eurjchem-91 67 161     SPACE eurjchem-91 67 162 1h 1h NUM eurjchem-91 67 163     SPACE eurjchem-91 67 164 exchangeable exchangeable ADJ eurjchem-91 67 165     SPACE eurjchem-91 67 166 with with ADP eurjchem-91 67 167     SPACE eurjchem-91 67 168 d2o d2o NOUN eurjchem-91 67 169 , , PUNCT eurjchem-91 67 170     SPACE eurjchem-91 67 171 oh oh INTJ eurjchem-91 67 172 ) ) PUNCT eurjchem-91 67 173 . . PUNCT eurjchem-91 67 174     SPACE eurjchem-91 68 1 anal anal ADJ eurjchem-91 68 2 . . PUNCT eurjchem-91 68 3     SPACE eurjchem-91 68 4 calcd calcd NOUN eurjchem-91 68 5     SPACE eurjchem-91 68 6 for for ADP eurjchem-91 68 7     SPACE eurjchem-91 68 8 c23h15n3o6 c23h15n3o6 NOUN eurjchem-91 68 9     SPACE eurjchem-91 68 10 ( ( PUNCT eurjchem-91 68 11 429.38 429.38 NUM eurjchem-91 68 12 ): ): PUNCT eurjchem-91 68 13     SPACE eurjchem-91 68 14 c c NOUN eurjchem-91 68 15 , , PUNCT eurjchem-91 68 16     SPACE eurjchem-91 68 17 64.33 64.33 NUM eurjchem-91 68 18 ; ; PUNCT eurjchem-91 68 19     SPACE eurjchem-91 68 20 h h NOUN eurjchem-91 68 21 , , PUNCT eurjchem-91 68 22     SPACE eurjchem-91 68 23 3.51 3.51 NUM eurjchem-91 68 24 , , PUNCT eurjchem-91 68 25     SPACE eurjchem-91 68 26 n n CCONJ eurjchem-91 68 27 , , PUNCT eurjchem-91 68 28     SPACE eurjchem-91 68 29 9.79 9.79 NUM eurjchem-91 68 30 % % NOUN eurjchem-91 68 31 . . PUNCT eurjchem-91 68 32     SPACE eurjchem-91 68 33 found find VERB eurjchem-91 68 34 : : PUNCT eurjchem-91 68 35     SPACE eurjchem-91 68 36 c c X eurjchem-91 68 37 , , PUNCT eurjchem-91 68 38     SPACE eurjchem-91 68 39 64.33 64.33 NUM eurjchem-91 68 40 ; ; PUNCT eurjchem-91 68 41     SPACE eurjchem-91 68 42 h h NOUN eurjchem-91 68 43 , , PUNCT eurjchem-91 68 44     SPACE eurjchem-91 68 45 3.70 3.70 NUM eurjchem-91 68 46 ; ; PUNCT eurjchem-91 68 47     SPACE eurjchem-91 68 48 n n CCONJ eurjchem-91 68 49 , , PUNCT eurjchem-91 68 50     SPACE eurjchem-91 68 51 9.71 9.71 NUM eurjchem-91 68 52 % % NOUN eurjchem-91 68 53 . . PUNCT eurjchem-91 68 54         SPACE eurjchem-91 68 55 2.9 2.9 NUM eurjchem-91 68 56 . . PUNCT eurjchem-91 68 57     SPACE eurjchem-91 68 58 3­(2­amino­4­oxo­4h­chromen­3­yl)methylidene)­6­ 3­(2­amino­4­oxo­4h­chromen­3­yl)methylidene)­6­ NUM eurjchem-91 68 59 ethyl­2h­pyrano[3,2­c]quinoline­2,4,5(3h,6h)­trione ethyl­2h­pyrano[3,2­c]quinoline­2,4,5(3h,6h)­trione PROPN eurjchem-91 68 60     SPACE eurjchem-91 68 61 ( ( PUNCT eurjchem-91 68 62 14a 14a NOUN eurjchem-91 68 63 , , PUNCT eurjchem-91 68 64 b b NOUN eurjchem-91 68 65 ) ) PUNCT eurjchem-91 68 66         SPACE eurjchem-91 68 67 2.9.1 2.9.1 NUM eurjchem-91 68 68 . . PUNCT eurjchem-91 68 69     SPACE eurjchem-91 68 70 method method VERB eurjchem-91 68 71     SPACE eurjchem-91 68 72 a a DET eurjchem-91 68 73         SPACE eurjchem-91 68 74 a a DET eurjchem-91 68 75     SPACE eurjchem-91 68 76 mixture mixture NOUN eurjchem-91 68 77     SPACE eurjchem-91 68 78 of of ADP eurjchem-91 68 79     SPACE eurjchem-91 68 80 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 68 81     SPACE eurjchem-91 68 82 2 2 NUM eurjchem-91 68 83     SPACE eurjchem-91 68 84 ( ( PUNCT eurjchem-91 68 85 0.55 0.55 NUM eurjchem-91 68 86     SPACE eurjchem-91 68 87 g g NOUN eurjchem-91 68 88 , , PUNCT eurjchem-91 68 89     SPACE eurjchem-91 68 90 2 2 NUM eurjchem-91 68 91     SPACE eurjchem-91 68 92 mmol mmol NOUN eurjchem-91 68 93 ) ) PUNCT eurjchem-91 68 94     SPACE eurjchem-91 68 95 and and CCONJ eurjchem-91 68 96     SPACE eurjchem-91 68 97 2‐amino‐3‐ 2‐amino‐3‐ NUM eurjchem-91 68 98 formyl formyl NOUN eurjchem-91 68 99     SPACE eurjchem-91 68 100 chromones chromone NOUN eurjchem-91 68 101     SPACE eurjchem-91 68 102 12a 12a NOUN eurjchem-91 68 103 , , PUNCT eurjchem-91 68 104     SPACE eurjchem-91 68 105 b b NOUN eurjchem-91 68 106     SPACE eurjchem-91 68 107 ( ( PUNCT eurjchem-91 68 108 2 2 NUM eurjchem-91 68 109     SPACE eurjchem-91 68 110 mmol mmol NOUN eurjchem-91 68 111 ) ) PUNCT eurjchem-91 68 112     SPACE eurjchem-91 68 113 in in ADP eurjchem-91 68 114     SPACE eurjchem-91 68 115 dmf dmf PROPN eurjchem-91 68 116     SPACE eurjchem-91 68 117 ( ( PUNCT eurjchem-91 68 118 10 10 NUM eurjchem-91 68 119     SPACE eurjchem-91 68 120 ml ml NOUN eurjchem-91 68 121 ) ) PUNCT eurjchem-91 68 122     SPACE eurjchem-91 68 123 containing contain VERB eurjchem-91 68 124     SPACE eurjchem-91 68 125 few few ADJ eurjchem-91 68 126     SPACE eurjchem-91 68 127 drops drop VERB eurjchem-91 68 128     SPACE eurjchem-91 68 129 of of ADP eurjchem-91 68 130     SPACE eurjchem-91 68 131 piperidine piperidine NOUN eurjchem-91 68 132     SPACE eurjchem-91 68 133 was be AUX eurjchem-91 68 134     SPACE eurjchem-91 68 135 heated heat VERB eurjchem-91 68 136     SPACE eurjchem-91 68 137 at at ADP eurjchem-91 68 138     SPACE eurjchem-91 68 139 reflux reflux NOUN eurjchem-91 68 140     SPACE eurjchem-91 68 141 for for ADP eurjchem-91 68 142     SPACE eurjchem-91 68 143 2h 2h NUM eurjchem-91 68 144 . . PUNCT eurjchem-91 68 145     SPACE eurjchem-91 69 1 the the DET eurjchem-91 69 2     SPACE eurjchem-91 69 3 solid solid NOUN eurjchem-91 69 4     SPACE eurjchem-91 69 5 deposited deposit VERB eurjchem-91 69 6     SPACE eurjchem-91 69 7 after after SCONJ eurjchem-91 69 8     SPACE eurjchem-91 69 9 cooling cooling NOUN eurjchem-91 69 10     SPACE eurjchem-91 69 11 was be AUX eurjchem-91 69 12     SPACE eurjchem-91 69 13 filtered filter VERB eurjchem-91 69 14     SPACE eurjchem-91 69 15 and and CCONJ eurjchem-91 69 16     SPACE eurjchem-91 69 17 recrystallized recrystallize VERB eurjchem-91 69 18     SPACE eurjchem-91 69 19 from from ADP eurjchem-91 69 20     SPACE eurjchem-91 69 21 dmf dmf NOUN eurjchem-91 69 22     SPACE eurjchem-91 69 23 to to PART eurjchem-91 69 24     SPACE eurjchem-91 69 25 give give VERB eurjchem-91 69 26     SPACE eurjchem-91 69 27 14a 14a NOUN eurjchem-91 69 28 , , PUNCT eurjchem-91 69 29     SPACE eurjchem-91 69 30 b b NOUN eurjchem-91 69 31     SPACE eurjchem-91 69 32 as as ADV eurjchem-91 69 33     SPACE eurjchem-91 69 34 yellow yellow ADJ eurjchem-91 69 35     SPACE eurjchem-91 69 36 crystals crystal NOUN eurjchem-91 69 37     SPACE eurjchem-91 69 38 ( ( PUNCT eurjchem-91 69 39 scheme scheme NOUN eurjchem-91 69 40     SPACE eurjchem-91 69 41 5 5 NUM eurjchem-91 69 42 ) ) PUNCT eurjchem-91 69 43 . . PUNCT eurjchem-91 69 44         SPACE eurjchem-91 70 1 2.9.2 2.9.2 NUM eurjchem-91 70 2 . . PUNCT eurjchem-91 70 3     SPACE eurjchem-91 70 4 method method NOUN eurjchem-91 70 5     SPACE eurjchem-91 70 6 b b NOUN eurjchem-91 70 7         SPACE eurjchem-91 70 8 a a DET eurjchem-91 70 9     SPACE eurjchem-91 70 10 mixture mixture NOUN eurjchem-91 70 11     SPACE eurjchem-91 70 12 of of ADP eurjchem-91 70 13     SPACE eurjchem-91 70 14 compound compound NOUN eurjchem-91 70 15     SPACE eurjchem-91 70 16 1 1 NUM eurjchem-91 70 17     SPACE eurjchem-91 70 18 ( ( PUNCT eurjchem-91 70 19 0.514 0.514 NUM eurjchem-91 70 20     SPACE eurjchem-91 70 21 g g NOUN eurjchem-91 70 22 , , PUNCT eurjchem-91 70 23     SPACE eurjchem-91 70 24 2 2 NUM eurjchem-91 70 25     SPACE eurjchem-91 70 26 mmol mmol NOUN eurjchem-91 70 27 ) ) PUNCT eurjchem-91 70 28     SPACE eurjchem-91 70 29 and and CCONJ eurjchem-91 70 30     SPACE eurjchem-91 70 31 2‐amino‐3‐ 2‐amino‐3‐ NUM eurjchem-91 70 32 formylchromones formylchromone NOUN eurjchem-91 70 33     SPACE eurjchem-91 70 34 12a 12a NOUN eurjchem-91 70 35 , , PUNCT eurjchem-91 70 36     SPACE eurjchem-91 70 37 b b NOUN eurjchem-91 70 38     SPACE eurjchem-91 70 39 ( ( PUNCT eurjchem-91 70 40 2 2 NUM eurjchem-91 70 41     SPACE eurjchem-91 70 42 mmol mmol NOUN eurjchem-91 70 43 ) ) PUNCT eurjchem-91 70 44 , , PUNCT eurjchem-91 70 45     SPACE eurjchem-91 70 46 in in ADP eurjchem-91 70 47     SPACE eurjchem-91 70 48 glacial glacial ADJ eurjchem-91 70 49     SPACE eurjchem-91 70 50 acetic acetic ADJ eurjchem-91 70 51     SPACE eurjchem-91 70 52 acid acid NOUN eurjchem-91 70 53     SPACE eurjchem-91 70 54 ( ( PUNCT eurjchem-91 70 55 10 10 NUM eurjchem-91 70 56     SPACE eurjchem-91 70 57 ml ml NOUN eurjchem-91 70 58 ) ) PUNCT eurjchem-91 70 59     SPACE eurjchem-91 70 60 and and CCONJ eurjchem-91 70 61     SPACE eurjchem-91 70 62 freshly freshly ADV eurjchem-91 70 63     SPACE eurjchem-91 70 64 fused fuse VERB eurjchem-91 70 65     SPACE eurjchem-91 70 66 sodium sodium NOUN eurjchem-91 70 67     SPACE eurjchem-91 70 68 acetate acetate NOUN eurjchem-91 70 69     SPACE eurjchem-91 70 70 ( ( PUNCT eurjchem-91 70 71 0.2 0.2 NUM eurjchem-91 70 72     SPACE eurjchem-91 70 73 g g NOUN eurjchem-91 70 74 ) ) PUNCT eurjchem-91 70 75 , , PUNCT eurjchem-91 70 76     SPACE eurjchem-91 70 77 was be AUX eurjchem-91 70 78     SPACE eurjchem-91 70 79 heated heated ADJ eurjchem-91 70 80     SPACE eurjchem-91 70 81 at at ADP eurjchem-91 70 82     SPACE eurjchem-91 70 83 reflux reflux NOUN eurjchem-91 70 84     SPACE eurjchem-91 70 85 for for ADP eurjchem-91 70 86     SPACE eurjchem-91 70 87 2h 2h NUM eurjchem-91 70 88 . . PUNCT eurjchem-91 70 89     SPACE eurjchem-91 71 1 the the DET eurjchem-91 71 2     SPACE eurjchem-91 71 3 solid solid NOUN eurjchem-91 71 4     SPACE eurjchem-91 71 5 deposited deposit VERB eurjchem-91 71 6     SPACE eurjchem-91 71 7 after after SCONJ eurjchem-91 71 8     SPACE eurjchem-91 71 9 cooling cool VERB eurjchem-91 71 10     SPACE eurjchem-91 71 11 was be AUX eurjchem-91 71 12     SPACE eurjchem-91 71 13 filtered filter VERB eurjchem-91 71 14     SPACE eurjchem-91 71 15 and and CCONJ eurjchem-91 71 16     SPACE eurjchem-91 71 17 recrystallized recrystallize VERB eurjchem-91 71 18     SPACE eurjchem-91 71 19 from from ADP eurjchem-91 71 20     SPACE eurjchem-91 71 21 dmf dmf NOUN eurjchem-91 71 22     SPACE eurjchem-91 71 23 to to PART eurjchem-91 71 24     SPACE eurjchem-91 71 25 give give VERB eurjchem-91 71 26     SPACE eurjchem-91 71 27 14a 14a NOUN eurjchem-91 71 28 , , PUNCT eurjchem-91 71 29     SPACE eurjchem-91 71 30 b b NOUN eurjchem-91 71 31     SPACE eurjchem-91 71 32 as as ADV eurjchem-91 71 33     SPACE eurjchem-91 71 34 yellow yellow ADJ eurjchem-91 71 35     SPACE eurjchem-91 71 36 crystals crystal NOUN eurjchem-91 71 37     SPACE eurjchem-91 71 38 ( ( PUNCT eurjchem-91 71 39 scheme scheme NOUN eurjchem-91 71 40     SPACE eurjchem-91 71 41 5 5 NUM eurjchem-91 71 42 ) ) PUNCT eurjchem-91 71 43 . . PUNCT eurjchem-91 71 44           SPACE eurjchem-91 72 1 2.9.3 2.9.3 NUM eurjchem-91 72 2 . . PUNCT eurjchem-91 72 3     SPACE eurjchem-91 72 4 method method NOUN eurjchem-91 72 5     SPACE eurjchem-91 72 6 c c PROPN eurjchem-91 72 7         SPACE eurjchem-91 72 8 a a DET eurjchem-91 72 9     SPACE eurjchem-91 72 10 mixture mixture NOUN eurjchem-91 72 11     SPACE eurjchem-91 72 12 of of ADP eurjchem-91 72 13     SPACE eurjchem-91 72 14 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 72 15     SPACE eurjchem-91 72 16 2 2 NUM eurjchem-91 72 17     SPACE eurjchem-91 72 18 ( ( PUNCT eurjchem-91 72 19 0.55 0.55 NUM eurjchem-91 72 20     SPACE eurjchem-91 72 21 g g NOUN eurjchem-91 72 22 , , PUNCT eurjchem-91 72 23     SPACE eurjchem-91 72 24 2 2 NUM eurjchem-91 72 25     SPACE eurjchem-91 72 26 mmol mmol NOUN eurjchem-91 72 27 ) ) PUNCT eurjchem-91 72 28     SPACE eurjchem-91 72 29 and and CCONJ eurjchem-91 72 30     SPACE eurjchem-91 72 31 chromone‐ chromone‐ VERB eurjchem-91 72 32 3‐carbonitriles 3‐carbonitrile NOUN eurjchem-91 72 33     SPACE eurjchem-91 72 34 16a 16a NOUN eurjchem-91 72 35 , , PUNCT eurjchem-91 72 36     SPACE eurjchem-91 72 37 b b NOUN eurjchem-91 72 38     SPACE eurjchem-91 72 39 ( ( PUNCT eurjchem-91 72 40 2 2 NUM eurjchem-91 72 41     SPACE eurjchem-91 72 42 mmol mmol NOUN eurjchem-91 72 43 ) ) PUNCT eurjchem-91 72 44     SPACE eurjchem-91 72 45 in in ADP eurjchem-91 72 46     SPACE eurjchem-91 72 47 dmf dmf PROPN eurjchem-91 72 48     SPACE eurjchem-91 72 49 ( ( PUNCT eurjchem-91 72 50 10 10 NUM eurjchem-91 72 51     SPACE eurjchem-91 72 52 ml ml NOUN eurjchem-91 72 53 ) ) PUNCT eurjchem-91 72 54     SPACE eurjchem-91 72 55 containing contain VERB eurjchem-91 72 56     SPACE eurjchem-91 72 57 few few ADJ eurjchem-91 72 58     SPACE eurjchem-91 72 59 drops drop VERB eurjchem-91 72 60     SPACE eurjchem-91 72 61 of of ADP eurjchem-91 72 62     SPACE eurjchem-91 72 63 piperidine piperidine NOUN eurjchem-91 72 64     SPACE eurjchem-91 72 65 was be AUX eurjchem-91 72 66     SPACE eurjchem-91 72 67 heated heated ADJ eurjchem-91 72 68     SPACE eurjchem-91 72 69 at at ADP eurjchem-91 72 70     SPACE eurjchem-91 72 71 reflux reflux NOUN eurjchem-91 72 72     SPACE eurjchem-91 72 73 for for ADP eurjchem-91 72 74     SPACE eurjchem-91 72 75 1h 1h NUM eurjchem-91 72 76 . . PUNCT eurjchem-91 72 77     SPACE eurjchem-91 72 78 the the DET eurjchem-91 72 79     SPACE eurjchem-91 72 80 solid solid NOUN eurjchem-91 72 81     SPACE eurjchem-91 72 82 deposited deposit VERB eurjchem-91 72 83     SPACE eurjchem-91 72 84 after after SCONJ eurjchem-91 72 85     SPACE eurjchem-91 72 86 cooling cooling NOUN eurjchem-91 72 87     SPACE eurjchem-91 72 88 was be AUX eurjchem-91 72 89     SPACE eurjchem-91 72 90 filtered filter VERB eurjchem-91 72 91     SPACE eurjchem-91 72 92 and and CCONJ eurjchem-91 72 93     SPACE eurjchem-91 72 94 recrystallized recrystallize VERB eurjchem-91 72 95     SPACE eurjchem-91 72 96 from from ADP eurjchem-91 72 97     SPACE eurjchem-91 72 98 dmf dmf NOUN eurjchem-91 72 99     SPACE eurjchem-91 72 100 to to PART eurjchem-91 72 101     SPACE eurjchem-91 72 102 give give VERB eurjchem-91 72 103     SPACE eurjchem-91 72 104 14a 14a NOUN eurjchem-91 72 105 , , PUNCT eurjchem-91 72 106     SPACE eurjchem-91 72 107 b b NOUN eurjchem-91 72 108     SPACE eurjchem-91 72 109 as as ADV eurjchem-91 72 110     SPACE eurjchem-91 72 111 yellow yellow ADJ eurjchem-91 72 112     SPACE eurjchem-91 72 113 crystals crystal NOUN eurjchem-91 72 114     SPACE eurjchem-91 72 115 ( ( PUNCT eurjchem-91 72 116 scheme scheme NOUN eurjchem-91 72 117     SPACE eurjchem-91 72 118 6 6 NUM eurjchem-91 72 119 ) ) PUNCT eurjchem-91 72 120 . . PUNCT eurjchem-91 72 121       SPACE eurjchem-91 73 1 for for ADP eurjchem-91 73 2     SPACE eurjchem-91 73 3 compound compound NOUN eurjchem-91 73 4     SPACE eurjchem-91 73 5 14a 14a NOUN eurjchem-91 73 6 : : PUNCT eurjchem-91 73 7     SPACE eurjchem-91 73 8 m.p m.p PROPN eurjchem-91 73 9 . . PROPN eurjchem-91 73 10 : : PUNCT eurjchem-91 73 11     SPACE eurjchem-91 73 12 277 277 NUM eurjchem-91 73 13     SPACE eurjchem-91 73 14 ºc ºc PROPN eurjchem-91 73 15 . . PUNCT eurjchem-91 73 16     SPACE eurjchem-91 73 17 yield yield NOUN eurjchem-91 73 18 : : PUNCT eurjchem-91 73 19     SPACE eurjchem-91 73 20 48‐55 48‐55 NUM eurjchem-91 73 21 % % NOUN eurjchem-91 73 22 . . PUNCT eurjchem-91 73 23     SPACE eurjchem-91 74 1 ir ir VERB eurjchem-91 74 2     SPACE eurjchem-91 74 3 ( ( PUNCT eurjchem-91 74 4 kbr kbr PROPN eurjchem-91 74 5 , , PUNCT eurjchem-91 74 6     SPACE eurjchem-91 74 7 cm‐1 cm‐1 NOUN eurjchem-91 74 8 ): ): PUNCT eurjchem-91 74 9     SPACE eurjchem-91 74 10 3437 3437 NUM eurjchem-91 74 11     SPACE eurjchem-91 74 12 ( ( PUNCT eurjchem-91 74 13 nh2 nh2 PROPN eurjchem-91 74 14 ) ) PUNCT eurjchem-91 74 15 , , PUNCT eurjchem-91 74 16     SPACE eurjchem-91 74 17 3068 3068 NUM eurjchem-91 74 18     SPACE eurjchem-91 74 19 ( ( PUNCT eurjchem-91 74 20 charom charom NOUN eurjchem-91 74 21 . . PUNCT eurjchem-91 74 22 ) ) PUNCT eurjchem-91 74 23 , , PUNCT eurjchem-91 74 24     SPACE eurjchem-91 74 25 2977 2977 NUM eurjchem-91 74 26 , , PUNCT eurjchem-91 74 27     SPACE eurjchem-91 74 28 2933 2933 NUM eurjchem-91 74 29 , , PUNCT eurjchem-91 74 30     SPACE eurjchem-91 74 31 2867 2867 NUM eurjchem-91 74 32     SPACE eurjchem-91 74 33 ( ( PUNCT eurjchem-91 74 34 ch3 ch3 PROPN eurjchem-91 74 35 , , PUNCT eurjchem-91 74 36     SPACE eurjchem-91 74 37 ch2 ch2 PROPN eurjchem-91 74 38 ) ) PUNCT eurjchem-91 74 39 , , PUNCT eurjchem-91 74 40     SPACE eurjchem-91 74 41 1732 1732 NUM eurjchem-91 74 42     SPACE eurjchem-91 74 43 ( ( PUNCT eurjchem-91 74 44 oc oc PROPN eurjchem-91 74 45 = = NOUN eurjchem-91 74 46 o o NOUN eurjchem-91 74 47 ) ) PUNCT eurjchem-91 74 48 , , PUNCT eurjchem-91 74 49     SPACE eurjchem-91 74 50 1657 1657 NUM eurjchem-91 74 51     SPACE eurjchem-91 74 52 ( ( PUNCT eurjchem-91 74 53 c c X eurjchem-91 74 54 = = NOUN eurjchem-91 74 55 oγ‐pyrone oγ‐pyrone NOUN eurjchem-91 74 56     SPACE eurjchem-91 74 57 c c NOUN eurjchem-91 74 58 = = NOUN eurjchem-91 74 59 oquinolinone oquinolinone NOUN eurjchem-91 74 60     SPACE eurjchem-91 74 61 and and CCONJ eurjchem-91 74 62     SPACE eurjchem-91 74 63 c c NOUN eurjchem-91 74 64 = = NOUN eurjchem-91 74 65 oketone oketone NOUN eurjchem-91 74 66 ) ) PUNCT eurjchem-91 74 67 . . PUNCT eurjchem-91 74 68                   SPACE eurjchem-91 74 69 1h 1h NUM eurjchem-91 74 70     SPACE eurjchem-91 74 71 nmr nmr NOUN eurjchem-91 74 72     SPACE eurjchem-91 74 73 ( ( PUNCT eurjchem-91 74 74 dmso‐d6 dmso‐d6 PROPN eurjchem-91 74 75 , , PUNCT eurjchem-91 74 76     SPACE eurjchem-91 74 77 δ δ PROPN eurjchem-91 74 78 ): ): PUNCT eurjchem-91 74 79     SPACE eurjchem-91 74 80 1.29 1.29 NUM eurjchem-91 74 81     SPACE eurjchem-91 74 82 ( ( PUNCT eurjchem-91 74 83 t t PROPN eurjchem-91 74 84 , , PUNCT eurjchem-91 74 85     SPACE eurjchem-91 74 86 3h 3h NUM eurjchem-91 74 87 , , PUNCT eurjchem-91 74 88     SPACE eurjchem-91 74 89 ch3 ch3 PROPN eurjchem-91 74 90 ) ) PUNCT eurjchem-91 74 91 , , PUNCT eurjchem-91 74 92     SPACE eurjchem-91 74 93 4.24 4.24 NUM eurjchem-91 74 94     SPACE eurjchem-91 74 95 ( ( PUNCT eurjchem-91 74 96 q q NOUN eurjchem-91 74 97 , , PUNCT eurjchem-91 74 98     SPACE eurjchem-91 74 99 2h 2h NUM eurjchem-91 74 100 , , PUNCT eurjchem-91 74 101     SPACE eurjchem-91 74 102 ch2 ch2 NOUN eurjchem-91 74 103 ) ) PUNCT eurjchem-91 74 104 , , PUNCT eurjchem-91 74 105     SPACE eurjchem-91 74 106 7.22‐ 7.22‐ NUM eurjchem-91 74 107 7.84 7.84 NUM eurjchem-91 74 108     SPACE eurjchem-91 74 109 ( ( PUNCT eurjchem-91 74 110 m m PROPN eurjchem-91 74 111 , , PUNCT eurjchem-91 74 112     SPACE eurjchem-91 74 113 8h 8h NUM eurjchem-91 74 114 , , PUNCT eurjchem-91 74 115     SPACE eurjchem-91 74 116 ar‐h ar‐h NOUN eurjchem-91 74 117 ) ) PUNCT eurjchem-91 74 118 , , PUNCT eurjchem-91 74 119     SPACE eurjchem-91 74 120 8.02 8.02 NUM eurjchem-91 74 121     SPACE eurjchem-91 74 122 ( ( PUNCT eurjchem-91 74 123 s s PROPN eurjchem-91 74 124 , , PUNCT eurjchem-91 74 125     SPACE eurjchem-91 74 126 1h 1h NUM eurjchem-91 74 127 , , PUNCT eurjchem-91 74 128     SPACE eurjchem-91 74 129 chmethine chmethine NOUN eurjchem-91 74 130 ) ) PUNCT eurjchem-91 74 131 , , PUNCT eurjchem-91 74 132     SPACE eurjchem-91 74 133 8.40 8.40 NUM eurjchem-91 74 134     SPACE eurjchem-91 74 135 ( ( PUNCT eurjchem-91 74 136 br br PROPN eurjchem-91 74 137 , , PUNCT eurjchem-91 74 138     SPACE eurjchem-91 74 139 1h 1h NUM eurjchem-91 74 140     SPACE eurjchem-91 74 141 exchangeable exchangeable ADJ eurjchem-91 74 142     SPACE eurjchem-91 74 143 with with ADP eurjchem-91 74 144     SPACE eurjchem-91 74 145 d2o d2o NOUN eurjchem-91 74 146 , , PUNCT eurjchem-91 74 147     SPACE eurjchem-91 74 148 1h 1h NUM eurjchem-91 74 149     SPACE eurjchem-91 74 150 of of ADP eurjchem-91 74 151     SPACE eurjchem-91 74 152 nh2 nh2 PROPN eurjchem-91 74 153 ) ) PUNCT eurjchem-91 74 154 , , PUNCT eurjchem-91 74 155     SPACE eurjchem-91 74 156 8.99 8.99 NUM eurjchem-91 74 157     SPACE eurjchem-91 74 158 ( ( PUNCT eurjchem-91 74 159 br br PROPN eurjchem-91 74 160 , , PUNCT eurjchem-91 74 161     SPACE eurjchem-91 74 162 1h 1h NUM eurjchem-91 74 163     SPACE eurjchem-91 74 164 exchangeable exchangeable ADJ eurjchem-91 74 165     SPACE eurjchem-91 74 166 with with ADP eurjchem-91 74 167     SPACE eurjchem-91 74 168 d2o d2o NOUN eurjchem-91 74 169 , , PUNCT eurjchem-91 74 170     SPACE eurjchem-91 74 171 1h 1h NUM eurjchem-91 74 172     SPACE eurjchem-91 74 173 of of ADP eurjchem-91 74 174     SPACE eurjchem-91 74 175 nh2 nh2 PROPN eurjchem-91 74 176 ) ) PUNCT eurjchem-91 74 177 . . PUNCT eurjchem-91 74 178     SPACE eurjchem-91 75 1 m m PROPN eurjchem-91 75 2 / / SYM eurjchem-91 75 3 z z NOUN eurjchem-91 75 4     SPACE eurjchem-91 75 5 ( ( PUNCT eurjchem-91 75 6 relative relative ADJ eurjchem-91 75 7     SPACE eurjchem-91 75 8 intensity intensity NOUN eurjchem-91 75 9 ): ): PUNCT eurjchem-91 75 10     SPACE eurjchem-91 75 11 428 428 NUM eurjchem-91 75 12     SPACE eurjchem-91 75 13 ( ( PUNCT eurjchem-91 75 14 m+ m+ NUM eurjchem-91 75 15 , , PUNCT eurjchem-91 75 16     SPACE eurjchem-91 75 17 0.5 0.5 NUM eurjchem-91 75 18 ) ) PUNCT eurjchem-91 75 19 , , PUNCT eurjchem-91 75 20     SPACE eurjchem-91 75 21 342 342 NUM eurjchem-91 75 22     SPACE eurjchem-91 75 23 ( ( PUNCT eurjchem-91 75 24 87 87 NUM eurjchem-91 75 25 ) ) PUNCT eurjchem-91 75 26 , , PUNCT eurjchem-91 75 27     SPACE eurjchem-91 75 28 314 314 NUM eurjchem-91 75 29     SPACE eurjchem-91 75 30 ( ( PUNCT eurjchem-91 75 31 100 100 NUM eurjchem-91 75 32 ) ) PUNCT eurjchem-91 75 33 , , PUNCT eurjchem-91 75 34     SPACE eurjchem-91 75 35 297 297 NUM eurjchem-91 75 36     SPACE eurjchem-91 75 37 ( ( PUNCT eurjchem-91 75 38 42 42 NUM eurjchem-91 75 39 ) ) PUNCT eurjchem-91 75 40 , , PUNCT eurjchem-91 75 41     SPACE eurjchem-91 75 42 286 286 NUM eurjchem-91 75 43     SPACE eurjchem-91 75 44 ( ( PUNCT eurjchem-91 75 45 23 23 NUM eurjchem-91 75 46 ) ) PUNCT eurjchem-91 75 47 , , PUNCT eurjchem-91 75 48     SPACE eurjchem-91 75 49 268 268 NUM eurjchem-91 75 50     SPACE eurjchem-91 75 51 ( ( PUNCT eurjchem-91 75 52 3 3 NUM eurjchem-91 75 53 ) ) PUNCT eurjchem-91 75 54 , , PUNCT eurjchem-91 75 55     SPACE eurjchem-91 75 56 257 257 NUM eurjchem-91 75 57     SPACE eurjchem-91 75 58 ( ( PUNCT eurjchem-91 75 59 6 6 NUM eurjchem-91 75 60 ) ) PUNCT eurjchem-91 75 61 , , PUNCT eurjchem-91 75 62     SPACE eurjchem-91 75 63 241 241 NUM eurjchem-91 75 64     SPACE eurjchem-91 75 65 ( ( PUNCT eurjchem-91 75 66 6 6 NUM eurjchem-91 75 67 ) ) PUNCT eurjchem-91 75 68 , , PUNCT eurjchem-91 75 69     SPACE eurjchem-91 75 70 229 229 NUM eurjchem-91 75 71     SPACE eurjchem-91 75 72 ( ( PUNCT eurjchem-91 75 73 9 9 NUM eurjchem-91 75 74 ) ) PUNCT eurjchem-91 75 75 , , PUNCT eurjchem-91 75 76     SPACE eurjchem-91 75 77 214 214 NUM eurjchem-91 75 78     SPACE eurjchem-91 75 79 ( ( PUNCT eurjchem-91 75 80 8) 8) NUM eurjchem-91 75 81 , , PUNCT eurjchem-91 75 82     SPACE eurjchem-91 75 83 189 189 NUM eurjchem-91 75 84     SPACE eurjchem-91 75 85 ( ( PUNCT eurjchem-91 75 86 4 4 NUM eurjchem-91 75 87 ) ) PUNCT eurjchem-91 75 88 , , PUNCT eurjchem-91 75 89     SPACE eurjchem-91 75 90 171 171 NUM eurjchem-91 75 91     SPACE eurjchem-91 75 92 ( ( PUNCT eurjchem-91 75 93 4 4 NUM eurjchem-91 75 94 ) ) PUNCT eurjchem-91 75 95 , , PUNCT eurjchem-91 75 96     SPACE eurjchem-91 75 97 157 157 NUM eurjchem-91 75 98     SPACE eurjchem-91 75 99 ( ( PUNCT eurjchem-91 75 100 2 2 NUM eurjchem-91 75 101 ) ) PUNCT eurjchem-91 75 102 . . PUNCT eurjchem-91 75 103     SPACE eurjchem-91 76 1 anal.caled anal.cale VERB eurjchem-91 76 2     SPACE eurjchem-91 76 3 for for ADP eurjchem-91 76 4     SPACE eurjchem-91 76 5 c24h16 c24h16 PROPN eurjchem-91 76 6     SPACE eurjchem-91 76 7 n2o6 n2o6 AUX eurjchem-91 76 8     SPACE eurjchem-91 76 9 ( ( PUNCT eurjchem-91 76 10 428.39 428.39 NUM eurjchem-91 76 11 ): ): PUNCT eurjchem-91 76 12     SPACE eurjchem-91 76 13 c c NOUN eurjchem-91 76 14 , , PUNCT eurjchem-91 76 15     SPACE eurjchem-91 76 16 67.29 67.29 NUM eurjchem-91 76 17 ; ; PUNCT eurjchem-91 76 18     SPACE eurjchem-91 76 19 h h NOUN eurjchem-91 76 20 , , PUNCT eurjchem-91 76 21     SPACE eurjchem-91 76 22 3.76 3.76 NUM eurjchem-91 76 23 ; ; PUNCT eurjchem-91 76 24     SPACE eurjchem-91 76 25 n n CCONJ eurjchem-91 76 26 , , PUNCT eurjchem-91 76 27     SPACE eurjchem-91 76 28 6.54 6.54 NUM eurjchem-91 76 29 % % NOUN eurjchem-91 76 30 . . PUNCT eurjchem-91 76 31     SPACE eurjchem-91 77 1 found find VERB eurjchem-91 77 2 : : PUNCT eurjchem-91 77 3     SPACE eurjchem-91 77 4 c c X eurjchem-91 77 5 , , PUNCT eurjchem-91 77 6     SPACE eurjchem-91 77 7 67.24 67.24 NUM eurjchem-91 77 8 ; ; PUNCT eurjchem-91 77 9     SPACE eurjchem-91 77 10 h h NOUN eurjchem-91 77 11 , , PUNCT eurjchem-91 77 12     SPACE eurjchem-91 77 13 3.65 3.65 NUM eurjchem-91 77 14 ; ; PUNCT eurjchem-91 77 15     SPACE eurjchem-91 77 16 n n CCONJ eurjchem-91 77 17 , , PUNCT eurjchem-91 77 18     SPACE eurjchem-91 77 19 6.20 6.20 NUM eurjchem-91 77 20 % % NOUN eurjchem-91 77 21 . . PUNCT eurjchem-91 77 22     SPACE eurjchem-91 77 23 for for ADP eurjchem-91 77 24     SPACE eurjchem-91 77 25 compound compound NOUN eurjchem-91 77 26     SPACE eurjchem-91 77 27 14b 14b NUM eurjchem-91 77 28 : : PUNCT eurjchem-91 77 29     SPACE eurjchem-91 77 30 m.p m.p PROPN eurjchem-91 77 31 . . PROPN eurjchem-91 77 32 : : PUNCT eurjchem-91 77 33     SPACE eurjchem-91 77 34 213 213 NUM eurjchem-91 77 35     SPACE eurjchem-91 77 36 ºc ºc PROPN eurjchem-91 77 37 . . PUNCT eurjchem-91 77 38     SPACE eurjchem-91 77 39 yield yield NOUN eurjchem-91 77 40 : : PUNCT eurjchem-91 77 41     SPACE eurjchem-91 77 42 43‐51 43‐51 NUM eurjchem-91 77 43 % % NOUN eurjchem-91 77 44 . . PUNCT eurjchem-91 77 45     SPACE eurjchem-91 78 1 ir ir VERB eurjchem-91 78 2     SPACE eurjchem-91 78 3 ( ( PUNCT eurjchem-91 78 4 kbr kbr PROPN eurjchem-91 78 5 , , PUNCT eurjchem-91 78 6     SPACE eurjchem-91 78 7 cm‐1 cm‐1 NOUN eurjchem-91 78 8 ): ): PUNCT eurjchem-91 78 9     SPACE eurjchem-91 78 10 3438 3438 NUM eurjchem-91 78 11     SPACE eurjchem-91 78 12 ( ( PUNCT eurjchem-91 78 13 nh2 nh2 PROPN eurjchem-91 78 14 ) ) PUNCT eurjchem-91 78 15 , , PUNCT eurjchem-91 78 16     SPACE eurjchem-91 78 17 3076 3076 NUM eurjchem-91 78 18     SPACE eurjchem-91 78 19 ( ( PUNCT eurjchem-91 78 20 charom charom NOUN eurjchem-91 78 21 . . PUNCT eurjchem-91 78 22 ) ) PUNCT eurjchem-91 78 23 , , PUNCT eurjchem-91 78 24     SPACE eurjchem-91 78 25 2972 2972 NUM eurjchem-91 78 26 , , PUNCT eurjchem-91 78 27     SPACE eurjchem-91 78 28 2929 2929 NUM eurjchem-91 78 29     SPACE eurjchem-91 78 30 ( ( PUNCT eurjchem-91 78 31 ch2 ch2 PROPN eurjchem-91 78 32 , , PUNCT eurjchem-91 78 33     SPACE eurjchem-91 78 34 ch3 ch3 PROPN eurjchem-91 78 35 ) ) PUNCT eurjchem-91 78 36 , , PUNCT eurjchem-91 78 37     SPACE eurjchem-91 78 38 1736 1736 NUM eurjchem-91 78 39     SPACE eurjchem-91 78 40 ( ( PUNCT eurjchem-91 78 41 oc oc PROPN eurjchem-91 78 42 = = NOUN eurjchem-91 78 43 o o NOUN eurjchem-91 78 44 ) ) PUNCT eurjchem-91 78 45 , , PUNCT eurjchem-91 78 46     SPACE eurjchem-91 78 47 1661 1661 NUM eurjchem-91 78 48     SPACE eurjchem-91 78 49 ( ( PUNCT eurjchem-91 78 50 c c NOUN eurjchem-91 78 51 = = NOUN eurjchem-91 78 52 oγ‐pyrone oγ‐pyrone NOUN eurjchem-91 78 53 , , PUNCT eurjchem-91 78 54     SPACE eurjchem-91 78 55 c c NOUN eurjchem-91 78 56 = = NOUN eurjchem-91 78 57 oquinoline oquinoline NOUN eurjchem-91 78 58     SPACE eurjchem-91 78 59 and and CCONJ eurjchem-91 78 60     SPACE eurjchem-91 78 61 c c NOUN eurjchem-91 78 62 = = NOUN eurjchem-91 78 63 oketone oketone NOUN eurjchem-91 78 64 ) ) PUNCT eurjchem-91 78 65 . . PUNCT eurjchem-91 78 66     SPACE eurjchem-91 78 67 1h 1h NUM eurjchem-91 78 68     SPACE eurjchem-91 78 69 nmr nmr NOUN eurjchem-91 78 70     SPACE eurjchem-91 78 71 ( ( PUNCT eurjchem-91 78 72 dmso‐d6 dmso‐d6 PROPN eurjchem-91 78 73 , , PUNCT eurjchem-91 78 74     SPACE eurjchem-91 78 75 δ δ PROPN eurjchem-91 78 76 ): ): PUNCT eurjchem-91 78 77     SPACE eurjchem-91 78 78 1.31 1.31 NUM eurjchem-91 78 79     SPACE eurjchem-91 78 80 ( ( PUNCT eurjchem-91 78 81 t t PROPN eurjchem-91 78 82 , , PUNCT eurjchem-91 78 83     SPACE eurjchem-91 78 84 3h 3h NUM eurjchem-91 78 85 , , PUNCT eurjchem-91 78 86     SPACE eurjchem-91 78 87 ch3 ch3 PROPN eurjchem-91 78 88 ) ) PUNCT eurjchem-91 78 89 , , PUNCT eurjchem-91 78 90     SPACE eurjchem-91 78 91 3.76 3.76 NUM eurjchem-91 78 92     SPACE eurjchem-91 78 93 ( ( PUNCT eurjchem-91 78 94 br br PROPN eurjchem-91 78 95 , , PUNCT eurjchem-91 78 96     SPACE eurjchem-91 78 97 2h 2h NUM eurjchem-91 78 98 , , PUNCT eurjchem-91 78 99     SPACE eurjchem-91 78 100 ch2 ch2 NOUN eurjchem-91 78 101 ) ) PUNCT eurjchem-91 78 102 , , PUNCT eurjchem-91 78 103     SPACE eurjchem-91 78 104 4.37 4.37 NUM eurjchem-91 78 105     SPACE eurjchem-91 78 106 ( ( PUNCT eurjchem-91 78 107 q q ADJ eurjchem-91 78 108 , , PUNCT eurjchem-91 78 109     SPACE eurjchem-91 78 110 2h 2h NUM eurjchem-91 78 111 , , PUNCT eurjchem-91 78 112     SPACE eurjchem-91 78 113 ch2 ch2 NOUN eurjchem-91 78 114 ) ) PUNCT eurjchem-91 78 115 , , PUNCT eurjchem-91 78 116     SPACE eurjchem-91 78 117 5.18 5.18 NUM eurjchem-91 78 118     SPACE eurjchem-91 78 119 ( ( PUNCT eurjchem-91 78 120 m m PROPN eurjchem-91 78 121 , , PUNCT eurjchem-91 78 122     SPACE eurjchem-91 78 123 2h 2h NUM eurjchem-91 78 124 , , PUNCT eurjchem-91 78 125     SPACE eurjchem-91 78 126 ch ch NOUN eurjchem-91 78 127 = = NOUN eurjchem-91 78 128 ch2 ch2 PROPN eurjchem-91 78 129 ) ) PUNCT eurjchem-91 78 130 , , PUNCT eurjchem-91 78 131     SPACE eurjchem-91 78 132 6.15 6.15 NUM eurjchem-91 78 133     SPACE eurjchem-91 78 134 ( ( PUNCT eurjchem-91 78 135 m m PROPN eurjchem-91 78 136 , , PUNCT eurjchem-91 78 137     SPACE eurjchem-91 78 138 1h 1h NUM eurjchem-91 78 139 , , PUNCT eurjchem-91 78 140     SPACE eurjchem-91 78 141 ch ch NOUN eurjchem-91 78 142 = = NOUN eurjchem-91 78 143 ch2 ch2 PROPN eurjchem-91 78 144 ) ) PUNCT eurjchem-91 78 145 , , PUNCT eurjchem-91 78 146     SPACE eurjchem-91 78 147 7.25‐7.94 7.25‐7.94 NUM eurjchem-91 78 148     SPACE eurjchem-91 78 149 ( ( PUNCT eurjchem-91 78 150 m m PROPN eurjchem-91 78 151 , , PUNCT eurjchem-91 78 152     SPACE eurjchem-91 78 153 7h 7h PROPN eurjchem-91 78 154 , , PUNCT eurjchem-91 78 155     SPACE eurjchem-91 78 156 ar‐h ar‐h NOUN eurjchem-91 78 157 ) ) PUNCT eurjchem-91 78 158 , , PUNCT eurjchem-91 78 159     SPACE eurjchem-91 78 160 8.04 8.04 NUM eurjchem-91 78 161     SPACE eurjchem-91 78 162 ( ( PUNCT eurjchem-91 78 163 s s PROPN eurjchem-91 78 164 , , PUNCT eurjchem-91 78 165     SPACE eurjchem-91 78 166 1h 1h NUM eurjchem-91 78 167 , , PUNCT eurjchem-91 78 168     SPACE eurjchem-91 78 169 chmethine chmethine NOUN eurjchem-91 78 170 ) ) PUNCT eurjchem-91 78 171 , , PUNCT eurjchem-91 78 172     SPACE eurjchem-91 78 173 8.71 8.71 NUM eurjchem-91 78 174     SPACE eurjchem-91 78 175 ( ( PUNCT eurjchem-91 78 176 br br PROPN eurjchem-91 78 177 , , PUNCT eurjchem-91 78 178     SPACE eurjchem-91 78 179 1h 1h NUM eurjchem-91 78 180     SPACE eurjchem-91 78 181 exchangeable exchangeable ADJ eurjchem-91 78 182     SPACE eurjchem-91 78 183 with with ADP eurjchem-91 78 184     SPACE eurjchem-91 78 185 d2o d2o NOUN eurjchem-91 78 186 , , PUNCT eurjchem-91 78 187     SPACE eurjchem-91 78 188 1h 1h NUM eurjchem-91 78 189     SPACE eurjchem-91 78 190 of of ADP eurjchem-91 78 191     SPACE eurjchem-91 78 192 nh2 nh2 PROPN eurjchem-91 78 193 ) ) PUNCT eurjchem-91 78 194 , , PUNCT eurjchem-91 78 195     SPACE eurjchem-91 78 196 9.92 9.92 NUM eurjchem-91 78 197     SPACE eurjchem-91 78 198 ( ( PUNCT eurjchem-91 78 199 br br PROPN eurjchem-91 78 200 , , PUNCT eurjchem-91 78 201     SPACE eurjchem-91 78 202 1h 1h NUM eurjchem-91 78 203     SPACE eurjchem-91 78 204 exchangeable exchangeable ADJ eurjchem-91 78 205     SPACE eurjchem-91 78 206 with with ADP eurjchem-91 78 207     SPACE eurjchem-91 78 208 d2o d2o NOUN eurjchem-91 78 209     SPACE eurjchem-91 78 210 1h 1h NUM eurjchem-91 78 211     SPACE eurjchem-91 78 212 of of ADP eurjchem-91 78 213     SPACE eurjchem-91 78 214 nh2 nh2 PROPN eurjchem-91 78 215 ) ) PUNCT eurjchem-91 78 216 . . PUNCT eurjchem-91 78 217     SPACE eurjchem-91 79 1 anal anal ADJ eurjchem-91 79 2 . . PUNCT eurjchem-91 79 3     SPACE eurjchem-91 79 4 calcd calcd NOUN eurjchem-91 79 5     SPACE eurjchem-91 79 6 for for ADP eurjchem-91 79 7     SPACE eurjchem-91 79 8 c27h20n2o6 c27h20n2o6 NOUN eurjchem-91 79 9     SPACE eurjchem-91 79 10 ( ( PUNCT eurjchem-91 79 11 468.46 468.46 NUM eurjchem-91 79 12 ) ) PUNCT eurjchem-91 79 13 . . PUNCT eurjchem-91 79 14     SPACE eurjchem-91 80 1 c. c. PROPN eurjchem-91 80 2     SPACE eurjchem-91 80 3 69.22 69.22 NUM eurjchem-91 80 4 ; ; PUNCT eurjchem-91 80 5     SPACE eurjchem-91 80 6 h h NOUN eurjchem-91 80 7 , , PUNCT eurjchem-91 80 8     SPACE eurjchem-91 80 9 4.30 4.30 NUM eurjchem-91 80 10 , , PUNCT eurjchem-91 80 11     SPACE eurjchem-91 80 12 n n CCONJ eurjchem-91 80 13 , , PUNCT eurjchem-91 80 14     SPACE eurjchem-91 80 15 5.98 5.98 NUM eurjchem-91 80 16 % % NOUN eurjchem-91 80 17 . . PUNCT eurjchem-91 80 18     SPACE eurjchem-91 80 19 found find VERB eurjchem-91 80 20 : : PUNCT eurjchem-91 80 21     SPACE eurjchem-91 80 22 c c X eurjchem-91 80 23 , , PUNCT eurjchem-91 80 24     SPACE eurjchem-91 80 25 69.02 69.02 NUM eurjchem-91 80 26 ; ; PUNCT eurjchem-91 80 27     SPACE eurjchem-91 80 28 h h NOUN eurjchem-91 80 29 , , PUNCT eurjchem-91 80 30     SPACE eurjchem-91 80 31 4.07 4.07 NUM eurjchem-91 80 32 ; ; PUNCT eurjchem-91 80 33     SPACE eurjchem-91 80 34 n n CCONJ eurjchem-91 80 35 , , PUNCT eurjchem-91 80 36     SPACE eurjchem-91 80 37 5.72 5.72 NUM eurjchem-91 80 38 % % NOUN eurjchem-91 80 39 . . PUNCT eurjchem-91 80 40         SPACE eurjchem-91 81 1 3 3 NUM eurjchem-91 81 2 . . PUNCT eurjchem-91 81 3     SPACE eurjchem-91 81 4 results result VERB eurjchem-91 81 5     SPACE eurjchem-91 81 6 and and CCONJ eurjchem-91 81 7     SPACE eurjchem-91 81 8 discussion discussion NOUN eurjchem-91 81 9         SPACE eurjchem-91 81 10 in in ADP eurjchem-91 81 11     SPACE eurjchem-91 81 12 the the DET eurjchem-91 81 13     SPACE eurjchem-91 81 14 course course NOUN eurjchem-91 81 15     SPACE eurjchem-91 81 16 of of ADP eurjchem-91 81 17     SPACE eurjchem-91 81 18 the the DET eurjchem-91 81 19     SPACE eurjchem-91 81 20 present present ADJ eurjchem-91 81 21     SPACE eurjchem-91 81 22 work work NOUN eurjchem-91 81 23 , , PUNCT eurjchem-91 81 24     SPACE eurjchem-91 81 25 we we PRON eurjchem-91 81 26     SPACE eurjchem-91 81 27 found find VERB eurjchem-91 81 28 , , PUNCT eurjchem-91 81 29     SPACE eurjchem-91 81 30 warming warming NOUN eurjchem-91 81 31     SPACE eurjchem-91 81 32 pyranoquinolinone pyranoquinolinone NOUN eurjchem-91 81 33     SPACE eurjchem-91 81 34 ( ( PUNCT eurjchem-91 81 35 1 1 NUM eurjchem-91 81 36 ) ) PUNCT eurjchem-91 81 37     SPACE eurjchem-91 81 38 in in ADP eurjchem-91 81 39     SPACE eurjchem-91 81 40 sodium sodium NOUN eurjchem-91 81 41     SPACE eurjchem-91 81 42 hydroxide hydroxide NOUN eurjchem-91 81 43     SPACE eurjchem-91 81 44 solution solution NOUN eurjchem-91 81 45     SPACE eurjchem-91 81 46 ( ( PUNCT eurjchem-91 81 47 1n 1n NUM eurjchem-91 81 48 ) ) PUNCT eurjchem-91 81 49     SPACE eurjchem-91 81 50 at at ADP eurjchem-91 81 51     SPACE eurjchem-91 81 52 40‐50 40‐50 NUM eurjchem-91 81 53     SPACE eurjchem-91 81 54 ºc ºc PROPN eurjchem-91 81 55     SPACE eurjchem-91 81 56 for for ADP eurjchem-91 81 57     SPACE eurjchem-91 81 58 30 30 NUM eurjchem-91 81 59     SPACE eurjchem-91 81 60 min min NOUN eurjchem-91 81 61 . . PROPN eurjchem-91 81 62     SPACE eurjchem-91 81 63 afforded afford VERB eurjchem-91 81 64     SPACE eurjchem-91 81 65 the the DET eurjchem-91 81 66     SPACE eurjchem-91 81 67 novel novel NOUN eurjchem-91 81 68       SPACE eurjchem-91 81 69 3‐(1‐ethy1‐4‐hydroxy‐ 3‐(1‐ethy1‐4‐hydroxy‐ PROPN eurjchem-91 81 70 2‐oxo‐2(1h)‐quinolin‐3‐yl)‐3‐oxo‐propanoic 2‐oxo‐2(1h)‐quinolin‐3‐yl)‐3‐oxo‐propanoic NUM eurjchem-91 81 71     SPACE eurjchem-91 81 72 acid acid NOUN eurjchem-91 81 73     SPACE eurjchem-91 81 74 ( ( PUNCT eurjchem-91 81 75 2 2 NUM eurjchem-91 81 76 ) ) PUNCT eurjchem-91 81 77     SPACE eurjchem-91 81 78 in in ADP eurjchem-91 81 79     SPACE eurjchem-91 81 80 76 76 NUM eurjchem-91 81 81 % % NOUN eurjchem-91 81 82     SPACE eurjchem-91 81 83 yield yield NOUN eurjchem-91 81 84     SPACE eurjchem-91 81 85 ( ( PUNCT eurjchem-91 81 86 scheme scheme NOUN eurjchem-91 81 87     SPACE eurjchem-91 81 88 1 1 NUM eurjchem-91 81 89 ) ) PUNCT eurjchem-91 81 90 . . PUNCT eurjchem-91 81 91     SPACE eurjchem-91 82 1 structure structure NOUN eurjchem-91 82 2     SPACE eurjchem-91 82 3 of of ADP eurjchem-91 82 4     SPACE eurjchem-91 82 5 compound compound NOUN eurjchem-91 82 6     SPACE eurjchem-91 82 7 2 2 NUM eurjchem-91 82 8     SPACE eurjchem-91 82 9 was be AUX eurjchem-91 82 10     SPACE eurjchem-91 82 11 confirmed confirm VERB eurjchem-91 82 12     SPACE eurjchem-91 82 13 from from ADP eurjchem-91 82 14     SPACE eurjchem-91 82 15 its its PRON eurjchem-91 82 16     SPACE eurjchem-91 82 17 correct correct ADJ eurjchem-91 82 18     SPACE eurjchem-91 82 19 elemental elemental ADJ eurjchem-91 82 20     SPACE eurjchem-91 82 21 analysis analysis NOUN eurjchem-91 82 22     SPACE eurjchem-91 82 23 and and CCONJ eurjchem-91 82 24     SPACE eurjchem-91 82 25 spectral spectral ADJ eurjchem-91 82 26     SPACE eurjchem-91 82 27 data datum NOUN eurjchem-91 82 28 . . PUNCT eurjchem-91 82 29     SPACE eurjchem-91 83 1 the the DET eurjchem-91 83 2     SPACE eurjchem-91 83 3 1h 1h NUM eurjchem-91 83 4     SPACE eurjchem-91 83 5 nmr nmr NOUN eurjchem-91 83 6     SPACE eurjchem-91 83 7 spectrum spectrum NOUN eurjchem-91 83 8     SPACE eurjchem-91 83 9 showed show VERB eurjchem-91 83 10     SPACE eurjchem-91 83 11 a a DET eurjchem-91 83 12     SPACE eurjchem-91 83 13 characteristic characteristic ADJ eurjchem-91 83 14     SPACE eurjchem-91 83 15 singlet singlet NOUN eurjchem-91 83 16     SPACE eurjchem-91 83 17 signal signal NOUN eurjchem-91 83 18     SPACE eurjchem-91 83 19 at at ADP eurjchem-91 83 20     SPACE eurjchem-91 83 21 δ δ PROPN eurjchem-91 83 22     SPACE eurjchem-91 83 23 5.56 5.56 NUM eurjchem-91 83 24     SPACE eurjchem-91 83 25 ppm ppm AUX eurjchem-91 83 26     SPACE eurjchem-91 83 27 attributed attribute VERB eurjchem-91 83 28     SPACE eurjchem-91 83 29 to to ADP eurjchem-91 83 30     SPACE eurjchem-91 83 31 the the DET eurjchem-91 83 32     SPACE eurjchem-91 83 33 active active ADJ eurjchem-91 83 34     SPACE eurjchem-91 83 35 methylene methylene NOUN eurjchem-91 83 36     SPACE eurjchem-91 83 37 protons proton NOUN eurjchem-91 83 38 , , PUNCT eurjchem-91 83 39     SPACE eurjchem-91 83 40 in in ADP eurjchem-91 83 41     SPACE eurjchem-91 83 42 addition addition NOUN eurjchem-91 83 43     SPACE eurjchem-91 83 44 to to ADP eurjchem-91 83 45     SPACE eurjchem-91 83 46 two two NUM eurjchem-91 83 47     SPACE eurjchem-91 83 48 exchangeable exchangeable ADJ eurjchem-91 83 49     SPACE eurjchem-91 83 50 signals signal NOUN eurjchem-91 83 51     SPACE eurjchem-91 83 52 at at ADP eurjchem-91 83 53     SPACE eurjchem-91 83 54 δ δ PROPN eurjchem-91 83 55     SPACE eurjchem-91 83 56 12.02 12.02 NUM eurjchem-91 83 57     SPACE eurjchem-91 83 58 and and CCONJ eurjchem-91 83 59     SPACE eurjchem-91 83 60 13.41 13.41 NUM eurjchem-91 83 61     SPACE eurjchem-91 83 62 ppm ppm NOUN eurjchem-91 83 63     SPACE eurjchem-91 83 64 assigned assign VERB eurjchem-91 83 65     SPACE eurjchem-91 83 66 to to ADP eurjchem-91 83 67     SPACE eurjchem-91 83 68 2oh 2oh ADJ eurjchem-91 83 69     SPACE eurjchem-91 83 70 protons proton NOUN eurjchem-91 83 71 . . PUNCT eurjchem-91 83 72     SPACE eurjchem-91 84 1 the the DET eurjchem-91 84 2     SPACE eurjchem-91 84 3 mass mass NOUN eurjchem-91 84 4     SPACE eurjchem-91 84 5 spectrum spectrum NOUN eurjchem-91 84 6     SPACE eurjchem-91 84 7 of of ADP eurjchem-91 84 8     SPACE eurjchem-91 84 9 compound compound NOUN eurjchem-91 84 10     SPACE eurjchem-91 84 11 2 2 NUM eurjchem-91 84 12     SPACE eurjchem-91 84 13 did do AUX eurjchem-91 84 14     SPACE eurjchem-91 84 15 not not PART eurjchem-91 84 16     SPACE eurjchem-91 84 17 show show VERB eurjchem-91 84 18     SPACE eurjchem-91 84 19 the the DET eurjchem-91 84 20     SPACE eurjchem-91 84 21 molecular molecular ADJ eurjchem-91 84 22     SPACE eurjchem-91 84 23 ion ion NOUN eurjchem-91 84 24     SPACE eurjchem-91 84 25 peak peak NOUN eurjchem-91 84 26     SPACE eurjchem-91 84 27 at at ADP eurjchem-91 84 28     SPACE eurjchem-91 84 29 m m PROPN eurjchem-91 84 30 / / PROPN eurjchem-91 84 31 z z NOUN eurjchem-91 84 32     SPACE eurjchem-91 84 33 275 275 NUM eurjchem-91 84 34     SPACE eurjchem-91 84 35 but but CCONJ eurjchem-91 84 36     SPACE eurjchem-91 84 37 showed show VERB eurjchem-91 84 38     SPACE eurjchem-91 84 39 a a DET eurjchem-91 84 40     SPACE eurjchem-91 84 41 peak peak NOUN eurjchem-91 84 42     SPACE eurjchem-91 84 43 at at ADP eurjchem-91 84 44     SPACE eurjchem-91 84 45 m m PROPN eurjchem-91 84 46 / / PROPN eurjchem-91 85 1 z z NOUN eurjchem-91 85 2     SPACE eurjchem-91 85 3 257 257 NUM eurjchem-91 85 4     SPACE eurjchem-91 85 5 which which PRON eurjchem-91 85 6     SPACE eurjchem-91 85 7 was be AUX eurjchem-91 85 8     SPACE eurjchem-91 85 9 in in ADP eurjchem-91 85 10     SPACE eurjchem-91 85 11 agreement agreement NOUN eurjchem-91 85 12     SPACE eurjchem-91 85 13 with with ADP eurjchem-91 85 14     SPACE eurjchem-91 85 15 its its PRON eurjchem-91 85 16     SPACE eurjchem-91 85 17 molecular molecular ADJ eurjchem-91 85 18     SPACE eurjchem-91 85 19 mass mass NOUN eurjchem-91 85 20     SPACE eurjchem-91 85 21 after after ADP eurjchem-91 85 22     SPACE eurjchem-91 85 23 loss loss NOUN eurjchem-91 85 24     SPACE eurjchem-91 85 25 of of ADP eurjchem-91 85 26     SPACE eurjchem-91 85 27 one one NUM eurjchem-91 85 28     SPACE eurjchem-91 85 29 molecule molecule NOUN eurjchem-91 85 30     SPACE eurjchem-91 85 31 of of ADP eurjchem-91 85 32     SPACE eurjchem-91 85 33 water water NOUN eurjchem-91 85 34 , , PUNCT eurjchem-91 85 35     SPACE eurjchem-91 85 36 and and CCONJ eurjchem-91 85 37     SPACE eurjchem-91 85 38 the the DET eurjchem-91 85 39     SPACE eurjchem-91 85 40 base base NOUN eurjchem-91 85 41     SPACE eurjchem-91 85 42 peak peak NOUN eurjchem-91 85 43     SPACE eurjchem-91 85 44 at at ADP eurjchem-91 85 45     SPACE eurjchem-91 85 46 m m PROPN eurjchem-91 85 47 / / PROPN eurjchem-91 85 48 z z NOUN eurjchem-91 85 49     SPACE eurjchem-91 85 50 229 229 NUM eurjchem-91 85 51 . . PUNCT eurjchem-91 85 52     SPACE eurjchem-91 86 1 some some DET eurjchem-91 86 2     SPACE eurjchem-91 86 3 new new ADJ eurjchem-91 86 4     SPACE eurjchem-91 86 5 quinolinone quinolinone NOUN eurjchem-91 86 6     SPACE eurjchem-91 86 7 derivatives derivative NOUN eurjchem-91 86 8     SPACE eurjchem-91 86 9 were be AUX eurjchem-91 86 10     SPACE eurjchem-91 86 11 prepared prepare VERB eurjchem-91 86 12     SPACE eurjchem-91 86 13 from from ADP eurjchem-91 86 14     SPACE eurjchem-91 86 15 the the DET eurjchem-91 86 16     SPACE eurjchem-91 86 17 reaction reaction NOUN eurjchem-91 86 18     SPACE eurjchem-91 86 19 of of ADP eurjchem-91 86 20     SPACE eurjchem-91 86 21 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 86 22     SPACE eurjchem-91 86 23 2 2 NUM eurjchem-91 86 24     SPACE eurjchem-91 86 25 with with ADP eurjchem-91 86 26     SPACE eurjchem-91 86 27 different different ADJ eurjchem-91 86 28     SPACE eurjchem-91 86 29 ortho‐hydroxyaldehydes ortho‐hydroxyaldehyde NOUN eurjchem-91 86 30     SPACE eurjchem-91 86 31 and and CCONJ eurjchem-91 86 32     SPACE eurjchem-91 86 33 ortho‐aminoaldehydes ortho‐aminoaldehyde VERB eurjchem-91 86 34 . . PUNCT eurjchem-91 86 35     SPACE eurjchem-91 86 36 thus thus ADV eurjchem-91 86 37 , , PUNCT eurjchem-91 86 38     SPACE eurjchem-91 86 39 condensation condensation NOUN eurjchem-91 86 40     SPACE eurjchem-91 86 41 of of ADP eurjchem-91 86 42     SPACE eurjchem-91 86 43 2 2 NUM eurjchem-91 86 44     SPACE eurjchem-91 86 45 with with ADP eurjchem-91 86 46     SPACE eurjchem-91 86 47 salicylaldehyde salicylaldehyde NOUN eurjchem-91 86 48     SPACE eurjchem-91 86 49 in in ADP eurjchem-91 86 50     SPACE eurjchem-91 86 51 glacial glacial ADJ eurjchem-91 86 52     SPACE eurjchem-91 86 53 acetic acetic ADJ eurjchem-91 86 54     SPACE eurjchem-91 86 55 acid acid NOUN eurjchem-91 86 56     SPACE eurjchem-91 86 57 containing contain VERB eurjchem-91 86 58     SPACE eurjchem-91 86 59 freshly freshly ADV eurjchem-91 86 60     SPACE eurjchem-91 86 61 fused fuse VERB eurjchem-91 86 62     SPACE eurjchem-91 86 63 sodium sodium NOUN eurjchem-91 86 64     SPACE eurjchem-91 86 65 acetate acetate NOUN eurjchem-91 86 66     SPACE eurjchem-91 86 67 gave give VERB eurjchem-91 86 68     SPACE eurjchem-91 86 69 the the DET eurjchem-91 86 70     SPACE eurjchem-91 86 71 knoevenagel knoevenagel NOUN eurjchem-91 86 72     SPACE eurjchem-91 86 73 condensation condensation NOUN eurjchem-91 86 74     SPACE eurjchem-91 86 75 product product NOUN eurjchem-91 86 76     SPACE eurjchem-91 86 77 3 3 NUM eurjchem-91 86 78     SPACE eurjchem-91 86 79 ( ( PUNCT eurjchem-91 86 80 scheme scheme NOUN eurjchem-91 86 81     SPACE eurjchem-91 86 82 2 2 NUM eurjchem-91 86 83 ) ) PUNCT eurjchem-91 86 84 . . PUNCT eurjchem-91 86 85     SPACE eurjchem-91 87 1 the the DET eurjchem-91 87 2     SPACE eurjchem-91 87 3 1h 1h NUM eurjchem-91 87 4     SPACE eurjchem-91 87 5 nmr nmr NOUN eurjchem-91 87 6     SPACE eurjchem-91 87 7 spectrum spectrum NOUN eurjchem-91 87 8     SPACE eurjchem-91 87 9 of of ADP eurjchem-91 87 10     SPACE eurjchem-91 87 11 compound compound NOUN eurjchem-91 87 12     SPACE eurjchem-91 87 13 3 3 NUM eurjchem-91 87 14     SPACE eurjchem-91 87 15 revealed reveal VERB eurjchem-91 87 16     SPACE eurjchem-91 87 17 the the DET eurjchem-91 87 18     SPACE eurjchem-91 87 19 presence presence NOUN eurjchem-91 87 20     SPACE eurjchem-91 87 21 of of ADP eurjchem-91 87 22     SPACE eurjchem-91 87 23 two two NUM eurjchem-91 87 24     SPACE eurjchem-91 87 25 exchangeable exchangeable ADJ eurjchem-91 87 26     SPACE eurjchem-91 87 27 signals signal NOUN eurjchem-91 87 28     SPACE eurjchem-91 87 29 at at ADP eurjchem-91 87 30     SPACE eurjchem-91 87 31 δ δ PROPN eurjchem-91 87 32     SPACE eurjchem-91 87 33 11.71 11.71 NUM eurjchem-91 87 34     SPACE eurjchem-91 87 35 ( ( PUNCT eurjchem-91 87 36 ohsalicylaldehyde ohsalicylaldehyde NOUN eurjchem-91 87 37 ) ) PUNCT eurjchem-91 87 38     SPACE eurjchem-91 87 39 and and CCONJ eurjchem-91 87 40     SPACE eurjchem-91 87 41 14.69 14.69 NUM eurjchem-91 87 42     SPACE eurjchem-91 87 43 ppm ppm NOUN eurjchem-91 87 44     SPACE eurjchem-91 87 45 ( ( PUNCT eurjchem-91 87 46 ohquinolinone ohquinolinone NOUN eurjchem-91 87 47     SPACE eurjchem-91 87 48 and and CCONJ eurjchem-91 87 49     SPACE eurjchem-91 87 50 ohcarboxy ohcarboxy NOUN eurjchem-91 87 51 ) ) PUNCT eurjchem-91 87 52 . . PUNCT eurjchem-91 87 53     SPACE eurjchem-91 88 1 compound compound NOUN eurjchem-91 88 2     SPACE eurjchem-91 88 3 3 3 NUM eurjchem-91 88 4     SPACE eurjchem-91 88 5 can can AUX eurjchem-91 88 6     SPACE eurjchem-91 88 7 undergo undergo VERB eurjchem-91 88 8     SPACE eurjchem-91 88 9 intramolecular intramolecular ADJ eurjchem-91 88 10     SPACE eurjchem-91 88 11 cyclization cyclization NOUN eurjchem-91 88 12     SPACE eurjchem-91 88 13 in in ADP eurjchem-91 88 14     SPACE eurjchem-91 88 15 the the DET eurjchem-91 88 16     SPACE eurjchem-91 88 17 presence presence NOUN eurjchem-91 88 18     SPACE eurjchem-91 88 19 of of ADP eurjchem-91 88 20     SPACE eurjchem-91 88 21 concentrated concentrate VERB eurjchem-91 88 22     SPACE eurjchem-91 88 23 h2so4 h2so4 NOUN eurjchem-91 88 24     SPACE eurjchem-91 88 25 leading lead VERB eurjchem-91 88 26     SPACE eurjchem-91 88 27 to to ADP eurjchem-91 88 28     SPACE eurjchem-91 88 29 either either CCONJ eurjchem-91 88 30     SPACE eurjchem-91 88 31 pyranoquinoline pyranoquinoline NOUN eurjchem-91 88 32     SPACE eurjchem-91 88 33 derivative derivative NOUN eurjchem-91 88 34     SPACE eurjchem-91 88 35 4 4 NUM eurjchem-91 88 36     SPACE eurjchem-91 88 37 or or CCONJ eurjchem-91 88 38     SPACE eurjchem-91 88 39 coumarine coumarine NOUN eurjchem-91 88 40     SPACE eurjchem-91 88 41 derivative derivative NOUN eurjchem-91 88 42     SPACE eurjchem-91 88 43 5 5 NUM eurjchem-91 88 44     SPACE eurjchem-91 88 45 ( ( PUNCT eurjchem-91 88 46 scheme scheme NOUN eurjchem-91 88 47     SPACE eurjchem-91 88 48 2 2 NUM eurjchem-91 88 49 ) ) PUNCT eurjchem-91 88 50 . . PUNCT eurjchem-91 88 51     SPACE eurjchem-91 89 1 the the DET eurjchem-91 89 2     SPACE eurjchem-91 89 3 product product NOUN eurjchem-91 89 4     SPACE eurjchem-91 89 5 obtained obtain VERB eurjchem-91 89 6     SPACE eurjchem-91 89 7 from from ADP eurjchem-91 89 8     SPACE eurjchem-91 89 9 this this DET eurjchem-91 89 10     SPACE eurjchem-91 89 11 reaction reaction NOUN eurjchem-91 89 12     SPACE eurjchem-91 89 13 was be AUX eurjchem-91 89 14     SPACE eurjchem-91 89 15 found find VERB eurjchem-91 89 16     SPACE eurjchem-91 89 17 to to PART eurjchem-91 89 18     SPACE eurjchem-91 89 19 be be AUX eurjchem-91 89 20     SPACE eurjchem-91 89 21 identical identical ADJ eurjchem-91 89 22     SPACE eurjchem-91 89 23 ( ( PUNCT eurjchem-91 89 24 the the DET eurjchem-91 89 25     SPACE eurjchem-91 89 26 same same ADJ eurjchem-91 89 27     SPACE eurjchem-91 89 28 mp mp NOUN eurjchem-91 89 29 , , PUNCT eurjchem-91 89 30     SPACE eurjchem-91 89 31 mixed mix VERB eurjchem-91 89 32     SPACE eurjchem-91 89 33 mp mp NOUN eurjchem-91 89 34     SPACE eurjchem-91 89 35 and and CCONJ eurjchem-91 89 36     SPACE eurjchem-91 89 37 identical identical ADJ eurjchem-91 89 38     SPACE eurjchem-91 89 39 spectra spectra NOUN eurjchem-91 89 40 ) ) PUNCT eurjchem-91 89 41     SPACE eurjchem-91 89 42 with with ADP eurjchem-91 89 43     SPACE eurjchem-91 89 44 the the DET eurjchem-91 89 45     SPACE eurjchem-91 89 46 product product NOUN eurjchem-91 89 47     SPACE eurjchem-91 89 48 obtained obtain VERB eurjchem-91 89 49     SPACE eurjchem-91 89 50 from from ADP eurjchem-91 89 51     SPACE eurjchem-91 89 52 the the DET eurjchem-91 89 53     SPACE eurjchem-91 89 54 reaction reaction NOUN eurjchem-91 89 55     SPACE eurjchem-91 89 56 of of ADP eurjchem-91 89 57     SPACE eurjchem-91 89 58 pyranoquinoline pyranoquinoline NOUN eurjchem-91 89 59     SPACE eurjchem-91 89 60 1 1 NUM eurjchem-91 89 61     SPACE eurjchem-91 89 62 and and CCONJ eurjchem-91 89 63     SPACE eurjchem-91 89 64 salicylaldehyde salicylaldehyde NOUN eurjchem-91 89 65 , , PUNCT eurjchem-91 89 66     SPACE eurjchem-91 89 67 in in ADP eurjchem-91 89 68     SPACE eurjchem-91 89 69 glacial glacial ADJ eurjchem-91 89 70     SPACE eurjchem-91 89 71 acetic acetic ADJ eurjchem-91 89 72     SPACE eurjchem-91 89 73 acid acid NOUN eurjchem-91 89 74     SPACE eurjchem-91 89 75 and and CCONJ eurjchem-91 89 76     SPACE eurjchem-91 89 77 freshly freshly ADV eurjchem-91 89 78     SPACE eurjchem-91 89 79 fused fuse VERB eurjchem-91 89 80     SPACE eurjchem-91 89 81 sodium sodium NOUN eurjchem-91 89 82     SPACE eurjchem-91 89 83 acetate acetate NOUN eurjchem-91 89 84 . . PUNCT eurjchem-91 89 85     SPACE eurjchem-91 89 86 therefore therefore ADV eurjchem-91 89 87 , , PUNCT eurjchem-91 89 88     SPACE eurjchem-91 89 89 cyclization cyclization NOUN eurjchem-91 89 90     SPACE eurjchem-91 89 91 of of ADP eurjchem-91 89 92     SPACE eurjchem-91 89 93 compound compound NOUN eurjchem-91 89 94       SPACE eurjchem-91 89 95 3 3 NUM eurjchem-91 89 96       SPACE eurjchem-91 89 97 in in ADP eurjchem-91 89 98       SPACE eurjchem-91 89 99 concentrated concentrated ADJ eurjchem-91 89 100           SPACE eurjchem-91 89 101 198 198 NUM eurjchem-91 89 102     SPACE eurjchem-91 89 103 ibrahim ibrahim PROPN eurjchem-91 89 104     SPACE eurjchem-91 89 105 et et PROPN eurjchem-91 89 106     SPACE eurjchem-91 89 107 al al PROPN eurjchem-91 89 108 . . PROPN eurjchem-91 89 109     SPACE eurjchem-91 89 110 / / SYM eurjchem-91 89 111     SPACE eurjchem-91 89 112 european european ADJ eurjchem-91 89 113     SPACE eurjchem-91 89 114 journal journal NOUN eurjchem-91 89 115     SPACE eurjchem-91 89 116 of of ADP eurjchem-91 89 117     SPACE eurjchem-91 89 118 chemistry chemistry NOUN eurjchem-91 89 119     SPACE eurjchem-91 89 120 1 1 NUM eurjchem-91 89 121     SPACE eurjchem-91 89 122 ( ( PUNCT eurjchem-91 89 123 3 3 NUM eurjchem-91 89 124 ) ) PUNCT eurjchem-91 89 125     SPACE eurjchem-91 89 126 ( ( PUNCT eurjchem-91 89 127 2010 2010 NUM eurjchem-91 89 128 ) ) PUNCT eurjchem-91 89 129     SPACE eurjchem-91 89 130 195­199 195­199 NUM eurjchem-91 89 131         SPACE eurjchem-91 89 132 on on ADP eurjchem-91 89 133 et et NOUN eurjchem-91 90 1 oh oh INTJ eurjchem-91 90 2 o o INTJ eurjchem-91 91 1 o o X eurjchem-91 91 2 o o X eurjchem-91 91 3 r r NOUN eurjchem-91 91 4 nh2 nh2 NOUN eurjchem-91 91 5 o o INTJ eurjchem-91 92 1 oh oh INTJ eurjchem-91 92 2 on on ADP eurjchem-91 92 3 o o NOUN eurjchem-91 92 4 o o X eurjchem-91 93 1 o o X eurjchem-91 93 2 o o X eurjchem-91 93 3 o o X eurjchem-91 93 4 h2n h2n NOUN eurjchem-91 93 5 et et NOUN eurjchem-91 93 6 r r NOUN eurjchem-91 93 7 r r NOUN eurjchem-91 93 8 oh2n oh2n PROPN eurjchem-91 93 9 o o NOUN eurjchem-91 93 10 on on ADP eurjchem-91 93 11 et et NOUN eurjchem-91 94 1 oh oh INTJ eurjchem-91 94 2 o o INTJ eurjchem-91 95 1 o o X eurjchem-91 95 2 o o X eurjchem-91 95 3 r r NOUN eurjchem-91 95 4 nh nh NOUN eurjchem-91 95 5 o o NOUN eurjchem-91 95 6 2 2 NUM eurjchem-91 96 1 + + CCONJ eurjchem-91 96 2 a a DET eurjchem-91 96 3 , , PUNCT eurjchem-91 96 4 r= r= ADJ eurjchem-91 96 5 h h PROPN eurjchem-91 96 6 b b PROPN eurjchem-91 96 7 , , PUNCT eurjchem-91 96 8 r= r= ADJ eurjchem-91 96 9 ch2ch ch2ch NOUN eurjchem-91 96 10 = = SYM eurjchem-91 96 11 ch2 ch2 PROPN eurjchem-91 96 12 dmf dmf PROPN eurjchem-91 96 13 / / SYM eurjchem-91 96 14 pip pip PROPN eurjchem-91 96 15 . . PROPN eurjchem-91 97 1 12 12 NUM eurjchem-91 97 2 13 13 NUM eurjchem-91 97 3 14 14 NUM eurjchem-91 97 4 15 15 NUM eurjchem-91 97 5 a a PRON eurjchem-91 97 6 , , PUNCT eurjchem-91 97 7 r r NOUN eurjchem-91 97 8 = = SYM eurjchem-91 97 9 h h NOUN eurjchem-91 97 10 b b NOUN eurjchem-91 97 11 , , PUNCT eurjchem-91 97 12 r r NOUN eurjchem-91 97 13 = = PUNCT eurjchem-91 97 14 ch2ch ch2ch NOUN eurjchem-91 97 15 = = PROPN eurjchem-91 97 16 ch2 ch2 PROPN eurjchem-91 97 17 gl gl PROPN eurjchem-91 97 18 . . PROPN eurjchem-91 97 19 acoh acoh PROPN eurjchem-91 97 20 1 1 NUM eurjchem-91 97 21 12a 12a NOUN eurjchem-91 97 22 , , PUNCT eurjchem-91 97 23 b+ b+ X eurjchem-91 97 24 naoac naoac VERB eurjchem-91 97 25 o o PROPN eurjchem-91 97 26 h h NOUN eurjchem-91 97 27     SPACE eurjchem-91 97 28 scheme scheme NOUN eurjchem-91 97 29     SPACE eurjchem-91 97 30 5 5 NUM eurjchem-91 97 31                     SPACE eurjchem-91 97 32 scheme scheme NOUN eurjchem-91 97 33     SPACE eurjchem-91 97 34 6 6 NUM eurjchem-91 97 35         SPACE eurjchem-91 97 36 ibrahim ibrahim PROPN eurjchem-91 97 37     SPACE eurjchem-91 97 38 et et PROPN eurjchem-91 97 39     SPACE eurjchem-91 97 40 al al PROPN eurjchem-91 97 41 . . PROPN eurjchem-91 97 42     SPACE eurjchem-91 97 43 / / SYM eurjchem-91 97 44     SPACE eurjchem-91 97 45 european european ADJ eurjchem-91 97 46     SPACE eurjchem-91 97 47 journal journal NOUN eurjchem-91 97 48     SPACE eurjchem-91 97 49 of of ADP eurjchem-91 97 50     SPACE eurjchem-91 97 51 chemistry chemistry NOUN eurjchem-91 97 52     SPACE eurjchem-91 97 53 1 1 NUM eurjchem-91 97 54     SPACE eurjchem-91 97 55 ( ( PUNCT eurjchem-91 97 56 3 3 NUM eurjchem-91 97 57 ) ) PUNCT eurjchem-91 97 58     SPACE eurjchem-91 97 59 ( ( PUNCT eurjchem-91 97 60 2010 2010 NUM eurjchem-91 97 61 ) ) PUNCT eurjchem-91 97 62     SPACE eurjchem-91 97 63 195­199 195­199 NUM eurjchem-91 97 64     SPACE eurjchem-91 97 65 199 199 NUM eurjchem-91 97 66     SPACE eurjchem-91 97 67 h2so4 h2so4 NOUN eurjchem-91 97 68     SPACE eurjchem-91 97 69 yielded yield VERB eurjchem-91 97 70     SPACE eurjchem-91 97 71 6‐ethyl‐3‐(2‐hydroxybenzylidene)pyrano[3,2‐ 6‐ethyl‐3‐(2‐hydroxybenzylidene)pyrano[3,2‐ NOUN eurjchem-91 97 72 c]quinoline‐2,4,5‐(3h,6h)‐trione c]quinoline‐2,4,5‐(3h,6h)‐trione NOUN eurjchem-91 97 73     SPACE eurjchem-91 97 74 ( ( PUNCT eurjchem-91 97 75 4 4 NUM eurjchem-91 97 76 ) ) PUNCT eurjchem-91 97 77     SPACE eurjchem-91 97 78 not not PART eurjchem-91 97 79     SPACE eurjchem-91 97 80 the the DET eurjchem-91 97 81     SPACE eurjchem-91 97 82 coumarine coumarine NOUN eurjchem-91 97 83     SPACE eurjchem-91 97 84 derivative derivative NOUN eurjchem-91 97 85     SPACE eurjchem-91 97 86 5 5 NUM eurjchem-91 97 87 . . PUNCT eurjchem-91 97 88     SPACE eurjchem-91 97 89 the the DET eurjchem-91 97 90     SPACE eurjchem-91 97 91 reaction reaction NOUN eurjchem-91 97 92     SPACE eurjchem-91 97 93 of of ADP eurjchem-91 97 94     SPACE eurjchem-91 97 95 pyranoquinoline pyranoquinoline NOUN eurjchem-91 97 96     SPACE eurjchem-91 97 97 1 1 NUM eurjchem-91 97 98     SPACE eurjchem-91 97 99 with with ADP eurjchem-91 97 100     SPACE eurjchem-91 97 101 salicylaldehyde salicylaldehyde NOUN eurjchem-91 97 102     SPACE eurjchem-91 97 103 proceeds proceed VERB eurjchem-91 97 104     SPACE eurjchem-91 97 105 through through ADP eurjchem-91 97 106     SPACE eurjchem-91 97 107 the the DET eurjchem-91 97 108     SPACE eurjchem-91 97 109 tautomeric tautomeric NOUN eurjchem-91 97 110     SPACE eurjchem-91 97 111 1,3‐dione 1,3‐dione NUM eurjchem-91 97 112     SPACE eurjchem-91 97 113 form form NOUN eurjchem-91 97 114 , , PUNCT eurjchem-91 97 115     SPACE eurjchem-91 97 116 which which PRON eurjchem-91 97 117     SPACE eurjchem-91 97 118 in in ADP eurjchem-91 97 119     SPACE eurjchem-91 97 120 turn turn NOUN eurjchem-91 97 121     SPACE eurjchem-91 97 122 possesses possess VERB eurjchem-91 97 123     SPACE eurjchem-91 97 124 an an DET eurjchem-91 97 125     SPACE eurjchem-91 97 126 active active ADJ eurjchem-91 97 127     SPACE eurjchem-91 97 128 methylene methylene NOUN eurjchem-91 97 129     SPACE eurjchem-91 97 130 group group NOUN eurjchem-91 97 131 . . PUNCT eurjchem-91 97 132     SPACE eurjchem-91 98 1 the the DET eurjchem-91 98 2     SPACE eurjchem-91 98 3 ir ir NOUN eurjchem-91 98 4     SPACE eurjchem-91 98 5 spectrum spectrum NOUN eurjchem-91 98 6     SPACE eurjchem-91 98 7 of of ADP eurjchem-91 98 8     SPACE eurjchem-91 98 9 compound compound NOUN eurjchem-91 98 10     SPACE eurjchem-91 98 11 4 4 NUM eurjchem-91 98 12     SPACE eurjchem-91 98 13 showed show VERB eurjchem-91 98 14     SPACE eurjchem-91 98 15 characteristic characteristic ADJ eurjchem-91 98 16     SPACE eurjchem-91 98 17 absorption absorption NOUN eurjchem-91 98 18     SPACE eurjchem-91 98 19 bands band NOUN eurjchem-91 98 20     SPACE eurjchem-91 98 21 at at ADP eurjchem-91 98 22     SPACE eurjchem-91 98 23 3430 3430 NUM eurjchem-91 98 24     SPACE eurjchem-91 98 25 ( ( PUNCT eurjchem-91 98 26 oh oh INTJ eurjchem-91 98 27 ) ) PUNCT eurjchem-91 98 28 , , PUNCT eurjchem-91 98 29     SPACE eurjchem-91 98 30 1725 1725 NUM eurjchem-91 98 31     SPACE eurjchem-91 98 32 ( ( PUNCT eurjchem-91 98 33 o‐c o‐c NOUN eurjchem-91 98 34 = = SYM eurjchem-91 98 35 o o NOUN eurjchem-91 98 36 ) ) PUNCT eurjchem-91 98 37     SPACE eurjchem-91 98 38 and and CCONJ eurjchem-91 98 39     SPACE eurjchem-91 98 40 1642 1642 NUM eurjchem-91 98 41     SPACE eurjchem-91 98 42 cm‐1 cm‐1 NOUN eurjchem-91 98 43     SPACE eurjchem-91 98 44 ( ( PUNCT eurjchem-91 98 45 c c NOUN eurjchem-91 98 46 = = NOUN eurjchem-91 98 47 o o NOUN eurjchem-91 98 48 ) ) PUNCT eurjchem-91 98 49 . . PUNCT eurjchem-91 98 50     SPACE eurjchem-91 99 1 the the DET eurjchem-91 99 2     SPACE eurjchem-91 99 3 methine methine ADJ eurjchem-91 99 4     SPACE eurjchem-91 99 5 proton proton NOUN eurjchem-91 99 6     SPACE eurjchem-91 99 7 observed observe VERB eurjchem-91 99 8     SPACE eurjchem-91 99 9 at at ADP eurjchem-91 99 10     SPACE eurjchem-91 99 11 δ δ PROPN eurjchem-91 99 12     SPACE eurjchem-91 99 13 8.13 8.13 NUM eurjchem-91 99 14     SPACE eurjchem-91 99 15 ppm ppm NOUN eurjchem-91 99 16     SPACE eurjchem-91 99 17 in in ADP eurjchem-91 99 18     SPACE eurjchem-91 99 19 the the DET eurjchem-91 99 20     SPACE eurjchem-91 99 21 1h 1h NUM eurjchem-91 99 22     SPACE eurjchem-91 99 23 nmr nmr NOUN eurjchem-91 99 24     SPACE eurjchem-91 99 25 spectrum spectrum NOUN eurjchem-91 99 26 , , PUNCT eurjchem-91 99 27     SPACE eurjchem-91 99 28 while while SCONJ eurjchem-91 99 29     SPACE eurjchem-91 99 30 the the DET eurjchem-91 99 31     SPACE eurjchem-91 99 32 methine methine ADJ eurjchem-91 99 33     SPACE eurjchem-91 99 34 carbon carbon NOUN eurjchem-91 99 35     SPACE eurjchem-91 99 36 appeared appear VERB eurjchem-91 99 37     SPACE eurjchem-91 99 38 at at ADP eurjchem-91 99 39     SPACE eurjchem-91 99 40 δ δ PROPN eurjchem-91 99 41     SPACE eurjchem-91 99 42 140.4 140.4 NUM eurjchem-91 99 43     SPACE eurjchem-91 99 44 ppm ppm NOUN eurjchem-91 99 45     SPACE eurjchem-91 99 46 in in ADP eurjchem-91 99 47     SPACE eurjchem-91 99 48 the the DET eurjchem-91 99 49     SPACE eurjchem-91 99 50 13cnmr 13cnmr NUM eurjchem-91 99 51     SPACE eurjchem-91 99 52 spectrum spectrum NOUN eurjchem-91 99 53 . . PUNCT eurjchem-91 99 54     SPACE eurjchem-91 100 1 the the DET eurjchem-91 100 2     SPACE eurjchem-91 100 3 structure structure NOUN eurjchem-91 100 4     SPACE eurjchem-91 100 5 of of ADP eurjchem-91 100 6     SPACE eurjchem-91 100 7 compound compound NOUN eurjchem-91 100 8     SPACE eurjchem-91 100 9 4 4 NUM eurjchem-91 100 10     SPACE eurjchem-91 100 11 was be AUX eurjchem-91 100 12     SPACE eurjchem-91 100 13 further far ADV eurjchem-91 100 14     SPACE eurjchem-91 100 15 deduced deduce VERB eurjchem-91 100 16     SPACE eurjchem-91 100 17 from from ADP eurjchem-91 100 18     SPACE eurjchem-91 100 19 its its PRON eurjchem-91 100 20     SPACE eurjchem-91 100 21 mass mass ADJ eurjchem-91 100 22     SPACE eurjchem-91 100 23 spectrum spectrum NOUN eurjchem-91 100 24     SPACE eurjchem-91 100 25 which which PRON eurjchem-91 100 26     SPACE eurjchem-91 100 27 revealed reveal VERB eurjchem-91 100 28     SPACE eurjchem-91 100 29 the the DET eurjchem-91 100 30     SPACE eurjchem-91 100 31 molecular molecular ADJ eurjchem-91 100 32     SPACE eurjchem-91 100 33 ion ion NOUN eurjchem-91 100 34     SPACE eurjchem-91 100 35 peak peak NOUN eurjchem-91 100 36     SPACE eurjchem-91 100 37 at at ADP eurjchem-91 100 38     SPACE eurjchem-91 100 39 m m PROPN eurjchem-91 100 40 / / PROPN eurjchem-91 100 41 z z NOUN eurjchem-91 100 42     SPACE eurjchem-91 100 43 361 361 NUM eurjchem-91 100 44     SPACE eurjchem-91 100 45 as as ADP eurjchem-91 100 46     SPACE eurjchem-91 100 47 the the DET eurjchem-91 100 48     SPACE eurjchem-91 100 49 base base NOUN eurjchem-91 100 50     SPACE eurjchem-91 100 51 peak peak NOUN eurjchem-91 100 52 , , PUNCT eurjchem-91 100 53     SPACE eurjchem-91 100 54 which which PRON eurjchem-91 100 55     SPACE eurjchem-91 100 56 is be AUX eurjchem-91 100 57     SPACE eurjchem-91 100 58 coincident coincident NOUN eurjchem-91 100 59     SPACE eurjchem-91 100 60 with with ADP eurjchem-91 100 61     SPACE eurjchem-91 100 62 the the DET eurjchem-91 100 63     SPACE eurjchem-91 100 64 formula formula NOUN eurjchem-91 100 65     SPACE eurjchem-91 100 66 weight weight NOUN eurjchem-91 100 67     SPACE eurjchem-91 100 68 ( ( PUNCT eurjchem-91 100 69 361.35 361.35 NUM eurjchem-91 100 70 ) ) PUNCT eurjchem-91 100 71     SPACE eurjchem-91 100 72 and and CCONJ eurjchem-91 100 73     SPACE eurjchem-91 100 74 support support VERB eurjchem-91 100 75     SPACE eurjchem-91 100 76 the the DET eurjchem-91 100 77     SPACE eurjchem-91 100 78 identity identity NOUN eurjchem-91 100 79     SPACE eurjchem-91 100 80 of of ADP eurjchem-91 100 81     SPACE eurjchem-91 100 82 the the DET eurjchem-91 100 83     SPACE eurjchem-91 100 84 structure structure NOUN eurjchem-91 100 85 . . PUNCT eurjchem-91 100 86     SPACE eurjchem-91 100 87 similarly similarly ADV eurjchem-91 100 88 , , PUNCT eurjchem-91 100 89     SPACE eurjchem-91 100 90 condensation condensation NOUN eurjchem-91 100 91     SPACE eurjchem-91 100 92 of of ADP eurjchem-91 100 93     SPACE eurjchem-91 100 94 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 100 95     SPACE eurjchem-91 100 96 2 2 NUM eurjchem-91 100 97     SPACE eurjchem-91 100 98 with with ADP eurjchem-91 100 99     SPACE eurjchem-91 100 100 2‐hydroxy‐1‐ 2‐hydroxy‐1‐ NUM eurjchem-91 100 101 naphthaldehyde naphthaldehyde NOUN eurjchem-91 100 102 , , PUNCT eurjchem-91 100 103     SPACE eurjchem-91 100 104 in in ADP eurjchem-91 100 105     SPACE eurjchem-91 100 106 glacial glacial ADJ eurjchem-91 100 107     SPACE eurjchem-91 100 108 acetic acetic ADJ eurjchem-91 100 109     SPACE eurjchem-91 100 110 acid acid NOUN eurjchem-91 100 111     SPACE eurjchem-91 100 112 and and CCONJ eurjchem-91 100 113     SPACE eurjchem-91 100 114 freshly freshly ADV eurjchem-91 100 115     SPACE eurjchem-91 100 116 fused fuse VERB eurjchem-91 100 117     SPACE eurjchem-91 100 118 sodium sodium NOUN eurjchem-91 100 119     SPACE eurjchem-91 100 120 acetate acetate NOUN eurjchem-91 100 121 , , PUNCT eurjchem-91 100 122     SPACE eurjchem-91 100 123 afforded afford VERB eurjchem-91 100 124     SPACE eurjchem-91 100 125 the the DET eurjchem-91 100 126     SPACE eurjchem-91 100 127 knoevenagel knoevenagel NOUN eurjchem-91 100 128     SPACE eurjchem-91 100 129 condensation condensation NOUN eurjchem-91 100 130     SPACE eurjchem-91 100 131 product product NOUN eurjchem-91 100 132     SPACE eurjchem-91 100 133 6 6 NUM eurjchem-91 100 134     SPACE eurjchem-91 100 135 which which DET eurjchem-91 100 136     SPACE eurjchem-91 100 137 underwent underwent NOUN eurjchem-91 100 138     SPACE eurjchem-91 100 139 intramolecular intramolecular ADJ eurjchem-91 100 140     SPACE eurjchem-91 100 141 cyclization cyclization NOUN eurjchem-91 100 142     SPACE eurjchem-91 100 143 in in ADP eurjchem-91 100 144     SPACE eurjchem-91 100 145 the the DET eurjchem-91 100 146     SPACE eurjchem-91 100 147 presence presence NOUN eurjchem-91 100 148     SPACE eurjchem-91 100 149 of of ADP eurjchem-91 100 150     SPACE eurjchem-91 100 151 concentrated concentrate VERB eurjchem-91 100 152     SPACE eurjchem-91 100 153 h2so4 h2so4 NOUN eurjchem-91 100 154     SPACE eurjchem-91 100 155 to to PART eurjchem-91 100 156     SPACE eurjchem-91 100 157 yield yield VERB eurjchem-91 100 158     SPACE eurjchem-91 100 159 6‐ethyl‐3‐(2‐hydroxy‐1‐ 6‐ethyl‐3‐(2‐hydroxy‐1‐ NUM eurjchem-91 100 160 naphthylidene)pyrano[3,2‐c]quinoline‐2,4,5‐(3h,6h)‐trione(7 naphthylidene)pyrano[3,2‐c]quinoline‐2,4,5‐(3h,6h)‐trione(7 NOUN eurjchem-91 100 161 ) ) PUNCT eurjchem-91 100 162 . . PUNCT eurjchem-91 100 163     SPACE eurjchem-91 101 1 compound compound NOUN eurjchem-91 101 2     SPACE eurjchem-91 101 3 7 7 NUM eurjchem-91 101 4     SPACE eurjchem-91 101 5 was be AUX eurjchem-91 101 6     SPACE eurjchem-91 101 7 also also ADV eurjchem-91 101 8     SPACE eurjchem-91 101 9 obtained obtain VERB eurjchem-91 101 10     SPACE eurjchem-91 101 11 from from ADP eurjchem-91 101 12     SPACE eurjchem-91 101 13 the the DET eurjchem-91 101 14     SPACE eurjchem-91 101 15 condensation condensation NOUN eurjchem-91 101 16     SPACE eurjchem-91 101 17 of of ADP eurjchem-91 101 18                         SPACE eurjchem-91 101 19 4‐hydroxypyranoquinoline 4‐hydroxypyranoquinoline NOUN eurjchem-91 101 20     SPACE eurjchem-91 101 21 derivative derivative NOUN eurjchem-91 101 22     SPACE eurjchem-91 101 23 1 1 NUM eurjchem-91 101 24     SPACE eurjchem-91 101 25 with with ADP eurjchem-91 101 26     SPACE eurjchem-91 101 27 2‐hydroxy‐1‐ 2‐hydroxy‐1‐ NUM eurjchem-91 101 28 naphthaldehyde naphthaldehyde NOUN eurjchem-91 101 29     SPACE eurjchem-91 101 30 ( ( PUNCT eurjchem-91 101 31 scheme scheme NOUN eurjchem-91 101 32     SPACE eurjchem-91 101 33 3 3 NUM eurjchem-91 101 34 ) ) PUNCT eurjchem-91 101 35 . . PUNCT eurjchem-91 101 36       SPACE eurjchem-91 102 1 interestingly interestingly ADV eurjchem-91 102 2 , , PUNCT eurjchem-91 102 3     SPACE eurjchem-91 102 4 condensation condensation NOUN eurjchem-91 102 5     SPACE eurjchem-91 102 6 of of ADP eurjchem-91 102 7     SPACE eurjchem-91 102 8 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 102 9     SPACE eurjchem-91 102 10 2 2 NUM eurjchem-91 102 11     SPACE eurjchem-91 102 12 with with ADP eurjchem-91 102 13     SPACE eurjchem-91 102 14 4‐hydroxy‐ 4‐hydroxy‐ NUM eurjchem-91 102 15 2‐oxo‐1‐phenyl‐1,2‐dihydroquinoline‐3‐carboxaldehyde 2‐oxo‐1‐phenyl‐1,2‐dihydroquinoline‐3‐carboxaldehyde NUM eurjchem-91 102 16     SPACE eurjchem-91 102 17 ( ( PUNCT eurjchem-91 102 18 8) 8) NOUN eurjchem-91 102 19     SPACE eurjchem-91 102 20 [ [ X eurjchem-91 102 21 19 19 NUM eurjchem-91 102 22 ] ] SYM eurjchem-91 102 23     SPACE eurjchem-91 102 24 and and CCONJ eurjchem-91 102 25     SPACE eurjchem-91 102 26 2‐hydroxy‐4‐oxo‐4h‐pyrido[1,2‐a]pyrimidine‐3‐ 2‐hydroxy‐4‐oxo‐4h‐pyrido[1,2‐a]pyrimidine‐3‐ NUM eurjchem-91 102 27 carboxaldehyde carboxaldehyde NOUN eurjchem-91 102 28     SPACE eurjchem-91 102 29 ( ( PUNCT eurjchem-91 102 30 9 9 NUM eurjchem-91 102 31 ) ) PUNCT eurjchem-91 102 32     SPACE eurjchem-91 103 1 [ [ X eurjchem-91 103 2 20 20 NUM eurjchem-91 103 3 ] ] SYM eurjchem-91 103 4     SPACE eurjchem-91 103 5 in in ADP eurjchem-91 103 6     SPACE eurjchem-91 103 7 boiling boiling NOUN eurjchem-91 103 8     SPACE eurjchem-91 103 9 dmf dmf PROPN eurjchem-91 103 10 , , PUNCT eurjchem-91 103 11     SPACE eurjchem-91 103 12 containing contain VERB eurjchem-91 103 13     SPACE eurjchem-91 103 14 few few ADJ eurjchem-91 103 15     SPACE eurjchem-91 103 16 drops drop VERB eurjchem-91 103 17     SPACE eurjchem-91 103 18 of of ADP eurjchem-91 103 19     SPACE eurjchem-91 103 20 piperidine piperidine NOUN eurjchem-91 103 21 , , PUNCT eurjchem-91 103 22     SPACE eurjchem-91 103 23 furnished furnish VERB eurjchem-91 103 24     SPACE eurjchem-91 103 25 directly directly ADV eurjchem-91 103 26     SPACE eurjchem-91 103 27 the the DET eurjchem-91 103 28     SPACE eurjchem-91 103 29 cyclized cyclized ADJ eurjchem-91 103 30     SPACE eurjchem-91 103 31 products product NOUN eurjchem-91 103 32 , , PUNCT eurjchem-91 103 33     SPACE eurjchem-91 103 34 6‐ethyl‐ 6‐ethyl‐ NUM eurjchem-91 103 35 3‐[(4‐hydroxy‐1‐phenyl‐2‐oxo‐1,2‐dihydroquinolin‐3‐yl)met 3‐[(4‐hydroxy‐1‐phenyl‐2‐oxo‐1,2‐dihydroquinolin‐3‐yl)met NUM eurjchem-91 103 36     SPACE eurjchem-91 103 37 hyldene‐2h‐pyrano[3,2‐c]quinoline‐2,4,5‐(3h,6h)‐trione hyldene‐2h‐pyrano[3,2‐c]quinoline‐2,4,5‐(3h,6h)‐trione NUM eurjchem-91 103 38     SPACE eurjchem-91 103 39 ( ( PUNCT eurjchem-91 103 40 10 10 NUM eurjchem-91 103 41 ) ) PUNCT eurjchem-91 103 42     SPACE eurjchem-91 103 43 and and CCONJ eurjchem-91 103 44     SPACE eurjchem-91 103 45 6‐ethyl‐3‐[(2‐hydroxy‐4‐oxo‐4h‐pyrido[1,2‐a]pyrimidin‐3‐ 6‐ethyl‐3‐[(2‐hydroxy‐4‐oxo‐4h‐pyrido[1,2‐a]pyrimidin‐3‐ NUM eurjchem-91 103 46 yl)methylidene]‐2h‐pyrano[3,2‐c]quinoline‐2,4,5‐(3h,6h)‐tri yl)methylidene]‐2h‐pyrano[3,2‐c]quinoline‐2,4,5‐(3h,6h)‐tri NUM eurjchem-91 103 47     SPACE eurjchem-91 103 48 one one NUM eurjchem-91 103 49     SPACE eurjchem-91 103 50 ( ( PUNCT eurjchem-91 103 51 11 11 NUM eurjchem-91 103 52 ) ) PUNCT eurjchem-91 103 53 , , PUNCT eurjchem-91 103 54     SPACE eurjchem-91 103 55 respectively respectively ADV eurjchem-91 103 56 , , PUNCT eurjchem-91 103 57     SPACE eurjchem-91 103 58 in in ADP eurjchem-91 103 59     SPACE eurjchem-91 103 60 one one NUM eurjchem-91 103 61     SPACE eurjchem-91 103 62 step step NOUN eurjchem-91 103 63     SPACE eurjchem-91 103 64 reactions reaction NOUN eurjchem-91 103 65 . . PUNCT eurjchem-91 103 66     SPACE eurjchem-91 104 1 under under ADP eurjchem-91 104 2     SPACE eurjchem-91 104 3 these these DET eurjchem-91 104 4     SPACE eurjchem-91 104 5 reaction reaction NOUN eurjchem-91 104 6     SPACE eurjchem-91 104 7 conditions condition NOUN eurjchem-91 104 8     SPACE eurjchem-91 104 9 the the DET eurjchem-91 104 10     SPACE eurjchem-91 104 11 knoevenagel knoevenagel NOUN eurjchem-91 104 12     SPACE eurjchem-91 104 13 condensation condensation NOUN eurjchem-91 104 14     SPACE eurjchem-91 104 15 intermediates intermediate NOUN eurjchem-91 104 16     SPACE eurjchem-91 104 17 were be AUX eurjchem-91 104 18     SPACE eurjchem-91 104 19 not not PART eurjchem-91 104 20     SPACE eurjchem-91 104 21 isolated isolate VERB eurjchem-91 104 22 , , PUNCT eurjchem-91 104 23     SPACE eurjchem-91 104 24 but but CCONJ eurjchem-91 104 25     SPACE eurjchem-91 104 26 underwent underwent NOUN eurjchem-91 104 27     SPACE eurjchem-91 104 28 intramolecular intramolecular ADJ eurjchem-91 104 29     SPACE eurjchem-91 104 30 nucleophilic nucleophilic ADJ eurjchem-91 104 31     SPACE eurjchem-91 104 32 lactonization lactonization NOUN eurjchem-91 104 33     SPACE eurjchem-91 104 34 to to PART eurjchem-91 104 35     SPACE eurjchem-91 104 36 form form VERB eurjchem-91 104 37     SPACE eurjchem-91 104 38 the the DET eurjchem-91 104 39     SPACE eurjchem-91 104 40 cyclized cyclized ADJ eurjchem-91 104 41     SPACE eurjchem-91 104 42 products product NOUN eurjchem-91 104 43     SPACE eurjchem-91 104 44 10 10 NUM eurjchem-91 104 45     SPACE eurjchem-91 104 46 and and CCONJ eurjchem-91 104 47     SPACE eurjchem-91 104 48 11 11 NUM eurjchem-91 104 49     SPACE eurjchem-91 104 50 ( ( PUNCT eurjchem-91 104 51 scheme scheme NOUN eurjchem-91 104 52     SPACE eurjchem-91 104 53 4 4 NUM eurjchem-91 104 54 ) ) PUNCT eurjchem-91 104 55 . . PUNCT eurjchem-91 104 56     SPACE eurjchem-91 105 1 on on ADP eurjchem-91 105 2     SPACE eurjchem-91 105 3 the the DET eurjchem-91 105 4     SPACE eurjchem-91 105 5 other other ADJ eurjchem-91 105 6     SPACE eurjchem-91 105 7 hand hand NOUN eurjchem-91 105 8 , , PUNCT eurjchem-91 105 9     SPACE eurjchem-91 105 10 when when SCONJ eurjchem-91 105 11     SPACE eurjchem-91 105 12 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 105 13     SPACE eurjchem-91 105 14 2 2 NUM eurjchem-91 105 15     SPACE eurjchem-91 105 16 was be AUX eurjchem-91 105 17     SPACE eurjchem-91 105 18 subjected subject VERB eurjchem-91 105 19     SPACE eurjchem-91 105 20 to to PART eurjchem-91 105 21     SPACE eurjchem-91 105 22 react react VERB eurjchem-91 105 23     SPACE eurjchem-91 105 24 with with ADP eurjchem-91 105 25     SPACE eurjchem-91 105 26 2‐amino 2‐amino NOUN eurjchem-91 105 27     SPACE eurjchem-91 105 28 chromone‐3‐carboxaldehyde chromone‐3‐carboxaldehyde NOUN eurjchem-91 105 29     SPACE eurjchem-91 105 30 ( ( PUNCT eurjchem-91 105 31 12a 12a NOUN eurjchem-91 105 32 ) ) PUNCT eurjchem-91 105 33     SPACE eurjchem-91 106 1 [ [ X eurjchem-91 106 2 21 21 NUM eurjchem-91 106 3 ] ] SYM eurjchem-91 106 4     SPACE eurjchem-91 106 5 and and CCONJ eurjchem-91 106 6     SPACE eurjchem-91 106 7 its its PRON eurjchem-91 106 8     SPACE eurjchem-91 106 9 8‐allyl 8‐allyl NUM eurjchem-91 106 10     SPACE eurjchem-91 106 11 analog analog NOUN eurjchem-91 106 12     SPACE eurjchem-91 106 13 12b 12b NOUN eurjchem-91 106 14 , , PUNCT eurjchem-91 106 15     SPACE eurjchem-91 107 1 [ [ X eurjchem-91 107 2 22 22 NUM eurjchem-91 107 3 ] ] SYM eurjchem-91 107 4     SPACE eurjchem-91 107 5 in in ADP eurjchem-91 107 6     SPACE eurjchem-91 107 7 boiling boiling NOUN eurjchem-91 107 8     SPACE eurjchem-91 107 9 dmf dmf PROPN eurjchem-91 107 10     SPACE eurjchem-91 107 11 containing contain VERB eurjchem-91 107 12     SPACE eurjchem-91 107 13 few few ADJ eurjchem-91 107 14     SPACE eurjchem-91 107 15 drops drop VERB eurjchem-91 107 16     SPACE eurjchem-91 107 17 of of ADP eurjchem-91 107 18     SPACE eurjchem-91 107 19 piperidine piperidine NOUN eurjchem-91 107 20     SPACE eurjchem-91 107 21 as as ADP eurjchem-91 107 22     SPACE eurjchem-91 107 23 a a DET eurjchem-91 107 24     SPACE eurjchem-91 107 25 catalyst catalyst NOUN eurjchem-91 107 26 , , PUNCT eurjchem-91 107 27     SPACE eurjchem-91 107 28 pyranoquinoline pyranoquinoline NOUN eurjchem-91 107 29     SPACE eurjchem-91 107 30 derivatives derivative NOUN eurjchem-91 107 31     SPACE eurjchem-91 107 32 14a 14a NOUN eurjchem-91 107 33 , , PUNCT eurjchem-91 107 34     SPACE eurjchem-91 107 35 b b NOUN eurjchem-91 107 36     SPACE eurjchem-91 107 37 or or CCONJ eurjchem-91 107 38     SPACE eurjchem-91 107 39 chromenopyridine chromenopyridine NOUN eurjchem-91 107 40     SPACE eurjchem-91 107 41 derivatives derivative NOUN eurjchem-91 107 42     SPACE eurjchem-91 107 43 15a 15a NOUN eurjchem-91 107 44 , , PUNCT eurjchem-91 107 45     SPACE eurjchem-91 107 46 b b NOUN eurjchem-91 107 47     SPACE eurjchem-91 107 48 were be AUX eurjchem-91 107 49     SPACE eurjchem-91 107 50 expected expect VERB eurjchem-91 107 51     SPACE eurjchem-91 107 52 as as ADP eurjchem-91 107 53     SPACE eurjchem-91 107 54 products product NOUN eurjchem-91 107 55     SPACE eurjchem-91 107 56 for for ADP eurjchem-91 107 57     SPACE eurjchem-91 107 58 this this DET eurjchem-91 107 59     SPACE eurjchem-91 107 60 reaction reaction NOUN eurjchem-91 107 61     SPACE eurjchem-91 107 62 ( ( PUNCT eurjchem-91 107 63 scheme scheme NOUN eurjchem-91 107 64     SPACE eurjchem-91 107 65 5 5 NUM eurjchem-91 107 66 ) ) PUNCT eurjchem-91 107 67 . . PUNCT eurjchem-91 107 68     SPACE eurjchem-91 108 1 herein herein NOUN eurjchem-91 108 2     SPACE eurjchem-91 108 3 again again ADV eurjchem-91 108 4 , , PUNCT eurjchem-91 108 5     SPACE eurjchem-91 108 6 the the DET eurjchem-91 108 7     SPACE eurjchem-91 108 8 reaction reaction NOUN eurjchem-91 108 9     SPACE eurjchem-91 108 10 proceeds proceed NOUN eurjchem-91 108 11     SPACE eurjchem-91 108 12 initially initially ADV eurjchem-91 108 13     SPACE eurjchem-91 108 14 via via ADP eurjchem-91 108 15     SPACE eurjchem-91 108 16 knoevenagel knoevenagel NOUN eurjchem-91 108 17     SPACE eurjchem-91 108 18 condensation condensation NOUN eurjchem-91 108 19     SPACE eurjchem-91 108 20 to to PART eurjchem-91 108 21     SPACE eurjchem-91 108 22 produce produce VERB eurjchem-91 108 23     SPACE eurjchem-91 108 24 the the DET eurjchem-91 108 25     SPACE eurjchem-91 108 26 intermediates intermediate NOUN eurjchem-91 108 27     SPACE eurjchem-91 108 28 13a 13a NOUN eurjchem-91 108 29     SPACE eurjchem-91 108 30 and and CCONJ eurjchem-91 108 31     SPACE eurjchem-91 108 32 13b 13b NOUN eurjchem-91 108 33 , , PUNCT eurjchem-91 108 34     SPACE eurjchem-91 108 35 respectively respectively ADV eurjchem-91 108 36 . . PUNCT eurjchem-91 108 37     SPACE eurjchem-91 108 38 these these DET eurjchem-91 108 39     SPACE eurjchem-91 108 40 intermediates intermediate NOUN eurjchem-91 108 41     SPACE eurjchem-91 108 42 can can AUX eurjchem-91 108 43     SPACE eurjchem-91 108 44 undergo undergo VERB eurjchem-91 108 45     SPACE eurjchem-91 108 46 intramolecular intramolecular ADJ eurjchem-91 108 47     SPACE eurjchem-91 108 48 nucleophilic nucleophilic ADJ eurjchem-91 108 49     SPACE eurjchem-91 108 50 lactonization lactonization NOUN eurjchem-91 108 51     SPACE eurjchem-91 108 52 forming form VERB eurjchem-91 108 53     SPACE eurjchem-91 108 54 pyranoquinoline pyranoquinoline NOUN eurjchem-91 108 55     SPACE eurjchem-91 108 56 derivatives derivative NOUN eurjchem-91 108 57     SPACE eurjchem-91 108 58 14a 14a NOUN eurjchem-91 108 59 , , PUNCT eurjchem-91 108 60     SPACE eurjchem-91 108 61 b b NOUN eurjchem-91 108 62     SPACE eurjchem-91 108 63 or or CCONJ eurjchem-91 108 64     SPACE eurjchem-91 108 65 lactimization lactimization NOUN eurjchem-91 108 66     SPACE eurjchem-91 108 67 forming form VERB eurjchem-91 108 68     SPACE eurjchem-91 108 69 chromenopyridine chromenopyridine NOUN eurjchem-91 108 70     SPACE eurjchem-91 108 71 derivatives derivative NOUN eurjchem-91 108 72     SPACE eurjchem-91 108 73 15a 15a NOUN eurjchem-91 108 74 , , PUNCT eurjchem-91 108 75     SPACE eurjchem-91 108 76 b. b. PROPN eurjchem-91 108 77     SPACE eurjchem-91 108 78 the the DET eurjchem-91 108 79     SPACE eurjchem-91 108 80 elemental elemental NOUN eurjchem-91 108 81     SPACE eurjchem-91 108 82 and and CCONJ eurjchem-91 108 83     SPACE eurjchem-91 108 84 mass mass ADJ eurjchem-91 108 85     SPACE eurjchem-91 108 86 analyses analysis NOUN eurjchem-91 108 87     SPACE eurjchem-91 108 88 of of ADP eurjchem-91 108 89     SPACE eurjchem-91 108 90 the the DET eurjchem-91 108 91     SPACE eurjchem-91 108 92 products product NOUN eurjchem-91 108 93     SPACE eurjchem-91 108 94 are be AUX eurjchem-91 108 95     SPACE eurjchem-91 108 96 not not PART eurjchem-91 108 97     SPACE eurjchem-91 108 98 differential differential VERB eurjchem-91 108 99     SPACE eurjchem-91 108 100 because because SCONJ eurjchem-91 108 101     SPACE eurjchem-91 108 102 both both DET eurjchem-91 108 103     SPACE eurjchem-91 108 104 structures structure NOUN eurjchem-91 108 105     SPACE eurjchem-91 108 106 are be AUX eurjchem-91 108 107     SPACE eurjchem-91 108 108 isomers isomer NOUN eurjchem-91 108 109 . . PUNCT eurjchem-91 108 110     SPACE eurjchem-91 109 1 the the DET eurjchem-91 109 2     SPACE eurjchem-91 109 3 1h 1h NUM eurjchem-91 109 4     SPACE eurjchem-91 109 5 nmr nmr NOUN eurjchem-91 109 6     SPACE eurjchem-91 109 7 spectra spectra NOUN eurjchem-91 109 8     SPACE eurjchem-91 109 9 were be AUX eurjchem-91 109 10     SPACE eurjchem-91 109 11 used use VERB eurjchem-91 109 12     SPACE eurjchem-91 109 13 to to PART eurjchem-91 109 14     SPACE eurjchem-91 109 15 distinguish distinguish VERB eurjchem-91 109 16     SPACE eurjchem-91 109 17 the the DET eurjchem-91 109 18     SPACE eurjchem-91 109 19 structure structure NOUN eurjchem-91 109 20     SPACE eurjchem-91 109 21 of of ADP eurjchem-91 109 22     SPACE eurjchem-91 109 23 the the DET eurjchem-91 109 24     SPACE eurjchem-91 109 25 products product NOUN eurjchem-91 109 26 . . PUNCT eurjchem-91 109 27     SPACE eurjchem-91 110 1 the the DET eurjchem-91 110 2     SPACE eurjchem-91 110 3 signals signal NOUN eurjchem-91 110 4     SPACE eurjchem-91 110 5 assigned assign VERB eurjchem-91 110 6     SPACE eurjchem-91 110 7 to to ADP eurjchem-91 110 8     SPACE eurjchem-91 110 9 the the DET eurjchem-91 110 10     SPACE eurjchem-91 110 11 oh oh NOUN eurjchem-91 110 12     SPACE eurjchem-91 110 13 and and CCONJ eurjchem-91 110 14     SPACE eurjchem-91 110 15 nh nh NOUN eurjchem-91 110 16     SPACE eurjchem-91 110 17 protons proton NOUN eurjchem-91 110 18     SPACE eurjchem-91 110 19 of of ADP eurjchem-91 110 20     SPACE eurjchem-91 110 21 compounds compound NOUN eurjchem-91 110 22     SPACE eurjchem-91 110 23 15a 15a NOUN eurjchem-91 110 24 , , PUNCT eurjchem-91 110 25     SPACE eurjchem-91 110 26 b b NOUN eurjchem-91 110 27     SPACE eurjchem-91 110 28 were be AUX eurjchem-91 110 29     SPACE eurjchem-91 110 30 not not PART eurjchem-91 110 31     SPACE eurjchem-91 110 32 observed observe VERB eurjchem-91 110 33     SPACE eurjchem-91 110 34 in in ADP eurjchem-91 110 35     SPACE eurjchem-91 110 36 the the DET eurjchem-91 110 37     SPACE eurjchem-91 110 38 spectra spectra NOUN eurjchem-91 110 39 , , PUNCT eurjchem-91 110 40     SPACE eurjchem-91 110 41 and and CCONJ eurjchem-91 110 42     SPACE eurjchem-91 110 43 therefore therefore ADV eurjchem-91 110 44     SPACE eurjchem-91 110 45 structures structure NOUN eurjchem-91 110 46     SPACE eurjchem-91 110 47 15a 15a NOUN eurjchem-91 110 48 , , PUNCT eurjchem-91 110 49     SPACE eurjchem-91 110 50 b b NOUN eurjchem-91 110 51     SPACE eurjchem-91 110 52 were be AUX eurjchem-91 110 53     SPACE eurjchem-91 110 54 excluded exclude VERB eurjchem-91 110 55 . . PUNCT eurjchem-91 110 56     SPACE eurjchem-91 110 57 the the DET eurjchem-91 110 58     SPACE eurjchem-91 110 59 spectra spectra NOUN eurjchem-91 110 60     SPACE eurjchem-91 110 61 of of ADP eurjchem-91 110 62     SPACE eurjchem-91 110 63 compounds compound NOUN eurjchem-91 110 64     SPACE eurjchem-91 110 65 14a 14a NOUN eurjchem-91 110 66 , , PUNCT eurjchem-91 110 67     SPACE eurjchem-91 110 68 b b NOUN eurjchem-91 110 69     SPACE eurjchem-91 110 70 showed show VERB eurjchem-91 110 71     SPACE eurjchem-91 110 72 characteristic characteristic ADJ eurjchem-91 110 73     SPACE eurjchem-91 110 74 exchangeable exchangeable ADJ eurjchem-91 110 75     SPACE eurjchem-91 110 76 signals signal NOUN eurjchem-91 110 77     SPACE eurjchem-91 110 78 attributed attribute VERB eurjchem-91 110 79     SPACE eurjchem-91 110 80 to to ADP eurjchem-91 110 81     SPACE eurjchem-91 110 82 the the DET eurjchem-91 110 83     SPACE eurjchem-91 110 84 nh2 nh2 NOUN eurjchem-91 110 85     SPACE eurjchem-91 110 86 protons proton NOUN eurjchem-91 110 87 . . PUNCT eurjchem-91 110 88     SPACE eurjchem-91 110 89 compounds compound VERB eurjchem-91 110 90     SPACE eurjchem-91 110 91 14a 14a NOUN eurjchem-91 110 92     SPACE eurjchem-91 110 93 and and CCONJ eurjchem-91 110 94     SPACE eurjchem-91 110 95 14b 14b NUM eurjchem-91 110 96     SPACE eurjchem-91 110 97 were be AUX eurjchem-91 110 98     SPACE eurjchem-91 110 99 also also ADV eurjchem-91 110 100     SPACE eurjchem-91 110 101 obtained obtain VERB eurjchem-91 110 102     SPACE eurjchem-91 110 103 from from ADP eurjchem-91 110 104     SPACE eurjchem-91 110 105 the the DET eurjchem-91 110 106     SPACE eurjchem-91 110 107 reaction reaction NOUN eurjchem-91 110 108     SPACE eurjchem-91 110 109 of of ADP eurjchem-91 110 110     SPACE eurjchem-91 110 111 pyranoquinoline pyranoquinoline NOUN eurjchem-91 110 112     SPACE eurjchem-91 110 113 1 1 NUM eurjchem-91 110 114     SPACE eurjchem-91 110 115 with with ADP eurjchem-91 110 116     SPACE eurjchem-91 110 117 2‐ 2‐ NUM eurjchem-91 110 118 aminochromone‐3‐carboxaldehydes aminochromone‐3‐carboxaldehyde NOUN eurjchem-91 110 119     SPACE eurjchem-91 110 120 ( ( PUNCT eurjchem-91 110 121 12a 12a NOUN eurjchem-91 110 122 , , PUNCT eurjchem-91 110 123     SPACE eurjchem-91 110 124 b b NOUN eurjchem-91 110 125 ) ) PUNCT eurjchem-91 110 126     SPACE eurjchem-91 110 127 in in ADP eurjchem-91 110 128     SPACE eurjchem-91 110 129 glacial glacial ADJ eurjchem-91 110 130     SPACE eurjchem-91 110 131 acetic acetic ADJ eurjchem-91 110 132     SPACE eurjchem-91 110 133 acid acid NOUN eurjchem-91 110 134     SPACE eurjchem-91 110 135 and and CCONJ eurjchem-91 110 136     SPACE eurjchem-91 110 137 freshly freshly ADV eurjchem-91 110 138     SPACE eurjchem-91 110 139 fused fuse VERB eurjchem-91 110 140     SPACE eurjchem-91 110 141 sodium sodium NOUN eurjchem-91 110 142     SPACE eurjchem-91 110 143 acetate acetate NOUN eurjchem-91 110 144 . . PUNCT eurjchem-91 110 145       SPACE eurjchem-91 110 146 in in ADP eurjchem-91 110 147     SPACE eurjchem-91 110 148 continuation continuation NOUN eurjchem-91 110 149     SPACE eurjchem-91 110 150 to to ADP eurjchem-91 110 151     SPACE eurjchem-91 110 152 our our PRON eurjchem-91 110 153     SPACE eurjchem-91 110 154 previous previous ADJ eurjchem-91 110 155     SPACE eurjchem-91 110 156 work work NOUN eurjchem-91 110 157     SPACE eurjchem-91 110 158 on on ADP eurjchem-91 110 159     SPACE eurjchem-91 110 160 the the DET eurjchem-91 110 161     SPACE eurjchem-91 110 162 chemistry chemistry NOUN eurjchem-91 110 163     SPACE eurjchem-91 110 164 of of ADP eurjchem-91 110 165     SPACE eurjchem-91 110 166 chromone‐3‐carbonitrile chromone‐3‐carbonitrile PROPN eurjchem-91 110 167     SPACE eurjchem-91 111 1 [ [ X eurjchem-91 111 2 23 23 NUM eurjchem-91 111 3 ] ] PUNCT eurjchem-91 111 4 , , PUNCT eurjchem-91 111 5     SPACE eurjchem-91 111 6 we we PRON eurjchem-91 111 7     SPACE eurjchem-91 111 8 found find VERB eurjchem-91 111 9     SPACE eurjchem-91 111 10 that that SCONJ eurjchem-91 111 11     SPACE eurjchem-91 111 12 2‐amino‐3‐ 2‐amino‐3‐ NUM eurjchem-91 111 13 formylchromone formylchromone NOUN eurjchem-91 111 14     SPACE eurjchem-91 111 15 is be AUX eurjchem-91 111 16     SPACE eurjchem-91 111 17 chemically chemically ADV eurjchem-91 111 18     SPACE eurjchem-91 111 19 equivalent equivalent NOUN eurjchem-91 111 20     SPACE eurjchem-91 111 21 to to PART eurjchem-91 111 22     SPACE eurjchem-91 111 23 chromone‐3‐ chromone‐3‐ VERB eurjchem-91 111 24 carbonitrile carbonitrile NOUN eurjchem-91 111 25     SPACE eurjchem-91 111 26 under under ADP eurjchem-91 111 27     SPACE eurjchem-91 111 28 certain certain ADJ eurjchem-91 111 29     SPACE eurjchem-91 111 30 nucleophilic nucleophilic ADJ eurjchem-91 111 31     SPACE eurjchem-91 111 32 conditions condition NOUN eurjchem-91 111 33 . . PUNCT eurjchem-91 111 34     SPACE eurjchem-91 112 1 thus thus ADV eurjchem-91 112 2 , , PUNCT eurjchem-91 112 3     SPACE eurjchem-91 112 4 treating treat VERB eurjchem-91 112 5     SPACE eurjchem-91 112 6 β‐ketoacid β‐ketoacid PUNCT eurjchem-91 112 7     SPACE eurjchem-91 112 8 2 2 NUM eurjchem-91 112 9     SPACE eurjchem-91 112 10 with with ADP eurjchem-91 112 11     SPACE eurjchem-91 112 12 chromone‐3‐carbonitriles chromone‐3‐carbonitrile NOUN eurjchem-91 112 13     SPACE eurjchem-91 112 14 ( ( PUNCT eurjchem-91 112 15 16a 16a NOUN eurjchem-91 112 16 , , PUNCT eurjchem-91 112 17     SPACE eurjchem-91 112 18 b b NOUN eurjchem-91 112 19 ) ) PUNCT eurjchem-91 112 20     SPACE eurjchem-91 113 1 [ [ X eurjchem-91 113 2 21,22 21,22 NOUN eurjchem-91 113 3 ] ] X eurjchem-91 113 4     SPACE eurjchem-91 113 5 in in ADP eurjchem-91 113 6     SPACE eurjchem-91 113 7 boiling boiling NOUN eurjchem-91 113 8     SPACE eurjchem-91 113 9 dmf dmf PROPN eurjchem-91 113 10     SPACE eurjchem-91 113 11 containing contain VERB eurjchem-91 113 12     SPACE eurjchem-91 113 13 few few ADJ eurjchem-91 113 14     SPACE eurjchem-91 113 15 drops drop VERB eurjchem-91 113 16     SPACE eurjchem-91 113 17 of of ADP eurjchem-91 113 18     SPACE eurjchem-91 113 19 piperidine piperidine NOUN eurjchem-91 113 20     SPACE eurjchem-91 113 21 afforded afford VERB eurjchem-91 113 22     SPACE eurjchem-91 113 23 compounds compound NOUN eurjchem-91 113 24     SPACE eurjchem-91 113 25 14a 14a NOUN eurjchem-91 113 26 , , PUNCT eurjchem-91 113 27     SPACE eurjchem-91 113 28 b. b. NOUN eurjchem-91 113 29     SPACE eurjchem-91 113 30 formation formation NOUN eurjchem-91 113 31     SPACE eurjchem-91 113 32 of of ADP eurjchem-91 113 33     SPACE eurjchem-91 113 34 compounds compound NOUN eurjchem-91 113 35     SPACE eurjchem-91 113 36 14a 14a NOUN eurjchem-91 113 37 , , PUNCT eurjchem-91 113 38     SPACE eurjchem-91 113 39 b b NOUN eurjchem-91 113 40     SPACE eurjchem-91 113 41 from from ADP eurjchem-91 113 42     SPACE eurjchem-91 113 43 carbonitriles carbonitrile NOUN eurjchem-91 113 44     SPACE eurjchem-91 113 45 16a 16a NOUN eurjchem-91 113 46 , , PUNCT eurjchem-91 113 47     SPACE eurjchem-91 113 48 b b NOUN eurjchem-91 113 49     SPACE eurjchem-91 113 50 was be AUX eurjchem-91 113 51     SPACE eurjchem-91 113 52 accomplished accomplish VERB eurjchem-91 113 53     SPACE eurjchem-91 113 54 via via ADP eurjchem-91 113 55     SPACE eurjchem-91 113 56 a a DET eurjchem-91 113 57     SPACE eurjchem-91 113 58 tandem tandem NOUN eurjchem-91 113 59     SPACE eurjchem-91 113 60 cyclization cyclization NOUN eurjchem-91 113 61     SPACE eurjchem-91 113 62 reaction reaction NOUN eurjchem-91 113 63     SPACE eurjchem-91 113 64 through through ADP eurjchem-91 113 65     SPACE eurjchem-91 113 66 michael michael PROPN eurjchem-91 113 67     SPACE eurjchem-91 113 68 addition addition NOUN eurjchem-91 113 69     SPACE eurjchem-91 113 70 of of ADP eurjchem-91 113 71     SPACE eurjchem-91 113 72 the the DET eurjchem-91 113 73     SPACE eurjchem-91 113 74 active active ADJ eurjchem-91 113 75     SPACE eurjchem-91 113 76 methylene methylene NOUN eurjchem-91 113 77     SPACE eurjchem-91 113 78 group group NOUN eurjchem-91 113 79     SPACE eurjchem-91 113 80 in in ADP eurjchem-91 113 81     SPACE eurjchem-91 113 82 compound compound NOUN eurjchem-91 113 83     SPACE eurjchem-91 113 84 2 2 NUM eurjchem-91 113 85     SPACE eurjchem-91 113 86 to to ADP eurjchem-91 113 87     SPACE eurjchem-91 113 88 the the DET eurjchem-91 113 89     SPACE eurjchem-91 113 90 γ‐pyrone γ‐pyrone NOUN eurjchem-91 113 91     SPACE eurjchem-91 113 92 moiety moiety NOUN eurjchem-91 113 93     SPACE eurjchem-91 113 94 of of ADP eurjchem-91 113 95     SPACE eurjchem-91 113 96 carbonitriles carbonitrile NOUN eurjchem-91 113 97     SPACE eurjchem-91 113 98 16a 16a NOUN eurjchem-91 113 99 , , PUNCT eurjchem-91 113 100     SPACE eurjchem-91 113 101 b b NOUN eurjchem-91 113 102     SPACE eurjchem-91 113 103 producing produce VERB eurjchem-91 113 104     SPACE eurjchem-91 113 105 intermediates intermediate NOUN eurjchem-91 113 106     SPACE eurjchem-91 113 107 a a DET eurjchem-91 113 108     SPACE eurjchem-91 113 109 ( ( PUNCT eurjchem-91 113 110 non‐isolable non‐isolable NUM eurjchem-91 113 111 ) ) PUNCT eurjchem-91 113 112 . . PUNCT eurjchem-91 113 113     SPACE eurjchem-91 114 1 the the DET eurjchem-91 114 2     SPACE eurjchem-91 114 3 base‐mediated base‐mediate VERB eurjchem-91 114 4     SPACE eurjchem-91 114 5 retro‐michael retro‐michael PROPN eurjchem-91 114 6     SPACE eurjchem-91 114 7 reaction reaction NOUN eurjchem-91 114 8     SPACE eurjchem-91 114 9 of of ADP eurjchem-91 114 10     SPACE eurjchem-91 114 11 a a PRON eurjchem-91 114 12     SPACE eurjchem-91 114 13 gave give VERB eurjchem-91 114 14     SPACE eurjchem-91 114 15 the the DET eurjchem-91 114 16     SPACE eurjchem-91 114 17 open open ADJ eurjchem-91 114 18     SPACE eurjchem-91 114 19 chain chain NOUN eurjchem-91 114 20     SPACE eurjchem-91 114 21 intermediates intermediate NOUN eurjchem-91 114 22     SPACE eurjchem-91 114 23 b b NOUN eurjchem-91 114 24     SPACE eurjchem-91 114 25 ( ( PUNCT eurjchem-91 114 26 non‐isolable non‐isolable ADJ eurjchem-91 114 27 ) ) PUNCT eurjchem-91 114 28 , , PUNCT eurjchem-91 114 29     SPACE eurjchem-91 114 30 the the DET eurjchem-91 114 31     SPACE eurjchem-91 114 32 attack attack NOUN eurjchem-91 114 33     SPACE eurjchem-91 114 34 of of ADP eurjchem-91 114 35     SPACE eurjchem-91 114 36 hydroxyl hydroxyl NOUN eurjchem-91 114 37     SPACE eurjchem-91 114 38 group group NOUN eurjchem-91 114 39     SPACE eurjchem-91 114 40 onto onto ADP eurjchem-91 114 41     SPACE eurjchem-91 114 42 the the DET eurjchem-91 114 43     SPACE eurjchem-91 114 44 nitrile nitrile ADJ eurjchem-91 114 45     SPACE eurjchem-91 114 46 function function NOUN eurjchem-91 114 47     SPACE eurjchem-91 114 48 gave give VERB eurjchem-91 114 49     SPACE eurjchem-91 114 50 intermediates intermediate NOUN eurjchem-91 114 51     SPACE eurjchem-91 114 52 c c NOUN eurjchem-91 114 53     SPACE eurjchem-91 114 54 ( ( PUNCT eurjchem-91 114 55 non‐ non‐ ADV eurjchem-91 114 56 isolable isolable ADJ eurjchem-91 114 57 ) ) PUNCT eurjchem-91 114 58     SPACE eurjchem-91 114 59 which which PRON eurjchem-91 114 60     SPACE eurjchem-91 114 61 underwent underwent NOUN eurjchem-91 114 62     SPACE eurjchem-91 114 63 lactonization lactonization NOUN eurjchem-91 114 64     SPACE eurjchem-91 114 65 leading lead VERB eurjchem-91 114 66     SPACE eurjchem-91 114 67 to to ADP eurjchem-91 114 68     SPACE eurjchem-91 114 69 14a 14a NOUN eurjchem-91 114 70 , , PUNCT eurjchem-91 114 71     SPACE eurjchem-91 114 72 b. b. PROPN eurjchem-91 114 73     SPACE eurjchem-91 114 74 the the DET eurjchem-91 114 75     SPACE eurjchem-91 114 76 transformation transformation NOUN eurjchem-91 114 77     SPACE eurjchem-91 114 78 of of ADP eurjchem-91 114 79     SPACE eurjchem-91 114 80 16 16 NUM eurjchem-91 114 81     SPACE eurjchem-91 114 82 into into ADP eurjchem-91 114 83     SPACE eurjchem-91 114 84 14 14 NUM eurjchem-91 114 85     SPACE eurjchem-91 114 86 can can AUX eurjchem-91 114 87     SPACE eurjchem-91 114 88 be be AUX eurjchem-91 114 89     SPACE eurjchem-91 114 90 regarded regard VERB eurjchem-91 114 91     SPACE eurjchem-91 114 92 as as ADP eurjchem-91 114 93     SPACE eurjchem-91 114 94 a a DET eurjchem-91 114 95     SPACE eurjchem-91 114 96 domino domino NOUN eurjchem-91 114 97     SPACE eurjchem-91 114 98 " " PUNCT eurjchem-91 114 99 michael michael PROPN eurjchem-91 114 100     SPACE eurjchem-91 114 101 / / SYM eurjchem-91 114 102     SPACE eurjchem-91 114 103 retro‐michael retro‐michael PROPN eurjchem-91 114 104     SPACE eurjchem-91 114 105 / / SYM eurjchem-91 114 106     SPACE eurjchem-91 114 107 nitrile‐addition nitrile‐addition NOUN eurjchem-91 114 108     SPACE eurjchem-91 114 109 / / SYM eurjchem-91 114 110     SPACE eurjchem-91 114 111 lactonization lactonization NOUN eurjchem-91 114 112 " " PUNCT eurjchem-91 114 113     SPACE eurjchem-91 114 114 as as SCONJ eurjchem-91 114 115     SPACE eurjchem-91 114 116 shown show VERB eurjchem-91 114 117     SPACE eurjchem-91 114 118 in in ADP eurjchem-91 114 119     SPACE eurjchem-91 114 120 scheme scheme NOUN eurjchem-91 114 121     SPACE eurjchem-91 114 122 6 6 NUM eurjchem-91 114 123     SPACE eurjchem-91 114 124 [ [ X eurjchem-91 114 125 24 24 NUM eurjchem-91 114 126 ] ] PUNCT eurjchem-91 114 127 . . PUNCT eurjchem-91 114 128           SPACE eurjchem-91 115 1 4 4 NUM eurjchem-91 115 2 . . PUNCT eurjchem-91 115 3     SPACE eurjchem-91 115 4 conclusion conclusion NOUN eurjchem-91 115 5         SPACE eurjchem-91 115 6 we we PRON eurjchem-91 115 7     SPACE eurjchem-91 115 8 have have AUX eurjchem-91 115 9     SPACE eurjchem-91 115 10 developed develop VERB eurjchem-91 115 11     SPACE eurjchem-91 115 12 a a DET eurjchem-91 115 13     SPACE eurjchem-91 115 14 new new ADJ eurjchem-91 115 15     SPACE eurjchem-91 115 16 and and CCONJ eurjchem-91 115 17     SPACE eurjchem-91 115 18 convenient convenient ADJ eurjchem-91 115 19     SPACE eurjchem-91 115 20 method method NOUN eurjchem-91 115 21     SPACE eurjchem-91 115 22 for for ADP eurjchem-91 115 23     SPACE eurjchem-91 115 24 the the DET eurjchem-91 115 25     SPACE eurjchem-91 115 26 synthesis synthesis NOUN eurjchem-91 115 27     SPACE eurjchem-91 115 28 of of ADP eurjchem-91 115 29     SPACE eurjchem-91 115 30 novel novel NOUN eurjchem-91 115 31     SPACE eurjchem-91 115 32 pyrano[3,2‐c]quinolinone pyrano[3,2‐c]quinolinone NOUN eurjchem-91 115 33     SPACE eurjchem-91 115 34 derivatives derivative NOUN eurjchem-91 115 35     SPACE eurjchem-91 115 36 via via ADP eurjchem-91 115 37     SPACE eurjchem-91 115 38 condensation condensation NOUN eurjchem-91 115 39     SPACE eurjchem-91 115 40 reactions reaction NOUN eurjchem-91 115 41     SPACE eurjchem-91 115 42 of of ADP eurjchem-91 115 43     SPACE eurjchem-91 115 44 3‐(1‐ethyl‐4‐hydroxy‐2‐oxo‐2(1h)‐ 3‐(1‐ethyl‐4‐hydroxy‐2‐oxo‐2(1h)‐ NUM eurjchem-91 115 45 quinolin‐3‐yl)‐3‐oxopropanoic quinolin‐3‐yl)‐3‐oxopropanoic ADJ eurjchem-91 115 46     SPACE eurjchem-91 115 47 acid acid NOUN eurjchem-91 115 48     SPACE eurjchem-91 115 49 with with ADP eurjchem-91 115 50     SPACE eurjchem-91 115 51 some some DET eurjchem-91 115 52     SPACE eurjchem-91 115 53 ortho‐ ortho‐ NOUN eurjchem-91 115 54 hydroxyaldehydes hydroxyaldehyde VERB eurjchem-91 115 55     SPACE eurjchem-91 115 56 and and CCONJ eurjchem-91 115 57     SPACE eurjchem-91 115 58 ortho‐aminoaldehydes ortho‐aminoaldehyde VERB eurjchem-91 115 59 . . PUNCT eurjchem-91 115 60         SPACE eurjchem-91 115 61 references reference NOUN eurjchem-91 115 62         SPACE eurjchem-91 116 1 [ [ X eurjchem-91 116 2 1 1 NUM eurjchem-91 116 3 ] ] PUNCT eurjchem-91 116 4 . . PUNCT eurjchem-91 117 1 darque darque ADJ eurjchem-91 117 2 , , PUNCT eurjchem-91 117 3     SPACE eurjchem-91 117 4 a. a. NOUN eurjchem-91 117 5 ; ; PUNCT eurjchem-91 117 6     SPACE eurjchem-91 117 7 dumètre dumètre NOUN eurjchem-91 117 8 , , PUNCT eurjchem-91 117 9     SPACE eurjchem-91 117 10 a. a. NOUN eurjchem-91 117 11 ; ; PUNCT eurjchem-91 117 12     SPACE eurjchem-91 117 13 hutter hutter NOUN eurjchem-91 117 14 , , PUNCT eurjchem-91 117 15     SPACE eurjchem-91 117 16 s. s. PROPN eurjchem-91 117 17 ; ; PUNCT eurjchem-91 117 18     SPACE eurjchem-91 117 19 casano casano PROPN eurjchem-91 117 20 , , PUNCT eurjchem-91 117 21     SPACE eurjchem-91 117 22 g. g. PROPN eurjchem-91 117 23 ; ; PUNCT eurjchem-91 117 24     SPACE eurjchem-91 117 25 robin robin PROPN eurjchem-91 117 26 , , PUNCT eurjchem-91 117 27     SPACE eurjchem-91 117 28 m. m. NOUN eurjchem-91 117 29 ; ; PUNCT eurjchem-91 117 30     SPACE eurjchem-91 117 31 pannecouque pannecouque NOUN eurjchem-91 117 32 , , PUNCT eurjchem-91 117 33     SPACE eurjchem-91 117 34 c. c. NOUN eurjchem-91 117 35 ; ; PUNCT eurjchem-91 117 36     SPACE eurjchem-91 117 37 azas aza NOUN eurjchem-91 117 38 , , PUNCT eurjchem-91 117 39     SPACE eurjchem-91 117 40 n. n. NOUN eurjchem-91 117 41     SPACE eurjchem-91 117 42 bioorg bioorg NOUN eurjchem-91 117 43 . . PUNCT eurjchem-91 117 44     SPACE eurjchem-91 118 1 med med PROPN eurjchem-91 118 2 . . PUNCT eurjchem-91 118 3     SPACE eurjchem-91 118 4 chem chem NOUN eurjchem-91 118 5 . . PUNCT eurjchem-91 118 6     SPACE eurjchem-91 118 7 lett lett PROPN eurjchem-91 118 8 . . PUNCT eurjchem-91 118 9     SPACE eurjchem-91 118 10 2009 2009 NUM eurjchem-91 118 11 , , PUNCT eurjchem-91 118 12     SPACE eurjchem-91 118 13 19 19 NUM eurjchem-91 118 14 , , PUNCT eurjchem-91 118 15     SPACE eurjchem-91 118 16 5962‐ 5962‐ NUM eurjchem-91 118 17 5964 5964 NUM eurjchem-91 118 18 . . PUNCT eurjchem-91 119 1 [ [ X eurjchem-91 119 2 2 2 NUM eurjchem-91 119 3 ] ] PUNCT eurjchem-91 119 4 . . PUNCT eurjchem-91 120 1 mizutani mizutani PROPN eurjchem-91 120 2 , , PUNCT eurjchem-91 120 3     SPACE eurjchem-91 120 4 n. n. NOUN eurjchem-91 120 5 ; ; PUNCT eurjchem-91 120 6     SPACE eurjchem-91 120 7 aoki aoki PROPN eurjchem-91 120 8 , , PUNCT eurjchem-91 120 9     SPACE eurjchem-91 120 10 y. y. NOUN eurjchem-91 120 11 ; ; PUNCT eurjchem-91 120 12     SPACE eurjchem-91 120 13 nabe nabe NOUN eurjchem-91 120 14 , , PUNCT eurjchem-91 120 15     SPACE eurjchem-91 120 16 t. t. PROPN eurjchem-91 120 17 ; ; PUNCT eurjchem-91 120 18     SPACE eurjchem-91 120 19 ishiwara ishiwara NOUN eurjchem-91 120 20 , , PUNCT eurjchem-91 120 21     SPACE eurjchem-91 120 22 m. m. NOUN eurjchem-91 120 23 ; ; PUNCT eurjchem-91 120 24     SPACE eurjchem-91 120 25 yoshino yoshino NOUN eurjchem-91 120 26 , , PUNCT eurjchem-91 120 27     SPACE eurjchem-91 120 28 s. s. PROPN eurjchem-91 120 29 ; ; PUNCT eurjchem-91 120 30     SPACE eurjchem-91 120 31 takagaki takagaki NOUN eurjchem-91 120 32 , , PUNCT eurjchem-91 120 33     SPACE eurjchem-91 120 34 h. h. PROPN eurjchem-91 120 35 ; ; PUNCT eurjchem-91 120 36     SPACE eurjchem-91 120 37 kohno kohno NOUN eurjchem-91 120 38 , , PUNCT eurjchem-91 120 39     SPACE eurjchem-91 120 40 s. s. PROPN eurjchem-91 120 41     SPACE eurjchem-91 120 42 eur eur PROPN eurjchem-91 120 43 . . PUNCT eurjchem-91 120 44     SPACE eurjchem-91 120 45 j. j. PROPN eurjchem-91 120 46     SPACE eurjchem-91 120 47 pharm pharm PROPN eurjchem-91 120 48 . . PUNCT eurjchem-91 120 49     SPACE eurjchem-91 120 50 2009 2009 NUM eurjchem-91 120 51 , , PUNCT eurjchem-91 120 52     SPACE eurjchem-91 120 53 602 602 NUM eurjchem-91 120 54 , , PUNCT eurjchem-91 120 55     SPACE eurjchem-91 120 56 138‐142 138‐142 NUM eurjchem-91 120 57 . . PUNCT eurjchem-91 120 58     SPACE eurjchem-91 121 1 [ [ X eurjchem-91 121 2 3 3 NUM eurjchem-91 121 3 ] ] PUNCT eurjchem-91 121 4 . . PUNCT eurjchem-91 121 5 di di PROPN eurjchem-91 121 6     SPACE eurjchem-91 121 7 santo santo PROPN eurjchem-91 121 8 , , PUNCT eurjchem-91 121 9     SPACE eurjchem-91 121 10 r. r. PROPN eurjchem-91 121 11 ; ; PUNCT eurjchem-91 121 12     SPACE eurjchem-91 121 13 costi costi NOUN eurjchem-91 121 14 , , PUNCT eurjchem-91 121 15     SPACE eurjchem-91 121 16 r. r. PROPN eurjchem-91 121 17 ; ; PUNCT eurjchem-91 121 18     SPACE eurjchem-91 121 19 roux roux NOUN eurjchem-91 121 20 , , PUNCT eurjchem-91 121 21     SPACE eurjchem-91 121 22 a. a. NOUN eurjchem-91 121 23 ; ; PUNCT eurjchem-91 121 24     SPACE eurjchem-91 121 25 miele miele PROPN eurjchem-91 121 26 , , PUNCT eurjchem-91 121 27     SPACE eurjchem-91 121 28 g. g. NOUN eurjchem-91 121 29 ; ; PUNCT eurjchem-91 121 30     SPACE eurjchem-91 121 31 crucitti crucitti NOUN eurjchem-91 121 32 , , PUNCT eurjchem-91 121 33     SPACE eurjchem-91 121 34 g. g. NOUN eurjchem-91 121 35     SPACE eurjchem-91 121 36 c. c. PROPN eurjchem-91 121 37 ; ; PUNCT eurjchem-91 121 38     SPACE eurjchem-91 121 39 iacovo iacovo PROPN eurjchem-91 121 40 , , PUNCT eurjchem-91 121 41     SPACE eurjchem-91 121 42 a. a. NOUN eurjchem-91 121 43 ; ; PUNCT eurjchem-91 121 44     SPACE eurjchem-91 121 45 rosi rosi PROPN eurjchem-91 121 46 , , PUNCT eurjchem-91 121 47     SPACE eurjchem-91 121 48 f. f. PROPN eurjchem-91 121 49 ; ; PUNCT eurjchem-91 121 50     SPACE eurjchem-91 121 51 marchand marchand PROPN eurjchem-91 121 52 , , PUNCT eurjchem-91 121 53     SPACE eurjchem-91 121 54 c. c. PROPN eurjchem-91 121 55     SPACE eurjchem-91 121 56 j. j. PROPN eurjchem-91 121 57     SPACE eurjchem-91 121 58 med med PROPN eurjchem-91 121 59 . . PUNCT eurjchem-91 121 60     SPACE eurjchem-91 121 61 chem chem NOUN eurjchem-91 121 62 . . PUNCT eurjchem-91 121 63     SPACE eurjchem-91 121 64 2008 2008 NUM eurjchem-91 121 65 , , PUNCT eurjchem-91 121 66     SPACE eurjchem-91 121 67 51 51 NUM eurjchem-91 121 68 , , PUNCT eurjchem-91 121 69     SPACE eurjchem-91 121 70 4744‐4750 4744‐4750 NUM eurjchem-91 121 71 . . PUNCT eurjchem-91 121 72     SPACE eurjchem-91 122 1 [ [ X eurjchem-91 122 2 4 4 NUM eurjchem-91 122 3 ] ] PUNCT eurjchem-91 122 4 . . PUNCT eurjchem-91 123 1 arya arya PROPN eurjchem-91 123 2 , , PUNCT eurjchem-91 123 3     SPACE eurjchem-91 123 4 k. k. PROPN eurjchem-91 123 5 ; ; PUNCT eurjchem-91 123 6     SPACE eurjchem-91 123 7 agarwal agarwal PROPN eurjchem-91 123 8 , , PUNCT eurjchem-91 123 9     SPACE eurjchem-91 123 10 m. m. NOUN eurjchem-91 123 11     SPACE eurjchem-91 123 12 bioorg bioorg PROPN eurjchem-91 123 13 . . PUNCT eurjchem-91 123 14     SPACE eurjchem-91 123 15 med med PROPN eurjchem-91 123 16 . . PUNCT eurjchem-91 123 17     SPACE eurjchem-91 123 18 chem chem NOUN eurjchem-91 123 19 . . PUNCT eurjchem-91 123 20     SPACE eurjchem-91 124 1 lett lett PROPN eurjchem-91 124 2 . . PUNCT eurjchem-91 124 3     SPACE eurjchem-91 125 1 2007 2007 NUM eurjchem-91 125 2 , , PUNCT eurjchem-91 125 3     SPACE eurjchem-91 125 4 17 17 NUM eurjchem-91 125 5 , , PUNCT eurjchem-91 125 6     SPACE eurjchem-91 125 7 86‐93 86‐93 NUM eurjchem-91 125 8 . . PUNCT eurjchem-91 125 9     SPACE eurjchem-91 126 1 [ [ X eurjchem-91 126 2 5 5 NUM eurjchem-91 126 3 ] ] PUNCT eurjchem-91 126 4 . . PUNCT eurjchem-91 127 1 el‐adly el‐adly ADV eurjchem-91 127 2 , , PUNCT eurjchem-91 127 3     SPACE eurjchem-91 127 4 r. r. PROPN eurjchem-91 127 5     SPACE eurjchem-91 127 6 a. a. NOUN eurjchem-91 127 7 ; ; PUNCT eurjchem-91 127 8     SPACE eurjchem-91 127 9 el el PROPN eurjchem-91 127 10 – – PUNCT eurjchem-91 127 11 sayed say VERB eurjchem-91 127 12 , , PUNCT eurjchem-91 127 13     SPACE eurjchem-91 127 14 s. s. PROPN eurjchem-91 127 15     SPACE eurjchem-91 127 16 m. m. NOUN eurjchem-91 127 17 ; ; PUNCT eurjchem-91 127 18     SPACE eurjchem-91 127 19 ismail ismail NOUN eurjchem-91 127 20 , , PUNCT eurjchem-91 127 21     SPACE eurjchem-91 127 22 m. m. NOUN eurjchem-91 127 23     SPACE eurjchem-91 127 24 m. m. NOUN eurjchem-91 127 25     SPACE eurjchem-91 127 26 synth synth NOUN eurjchem-91 127 27 . . PUNCT eurjchem-91 127 28     SPACE eurjchem-91 128 1 lubrication lubrication NOUN eurjchem-91 128 2     SPACE eurjchem-91 128 3 2005 2005 NUM eurjchem-91 128 4 , , PUNCT eurjchem-91 128 5     SPACE eurjchem-91 128 6 22 22 NUM eurjchem-91 128 7 , , PUNCT eurjchem-91 128 8     SPACE eurjchem-91 128 9 211‐223 211‐223 NUM eurjchem-91 128 10 . . PUNCT eurjchem-91 128 11       SPACE eurjchem-91 129 1 [ [ X eurjchem-91 129 2 6 6 NUM eurjchem-91 129 3 ] ] PUNCT eurjchem-91 129 4 . . PUNCT eurjchem-91 130 1 rivkin rivkin PROPN eurjchem-91 130 2 , , PUNCT eurjchem-91 130 3     SPACE eurjchem-91 130 4 a. a. NOUN eurjchem-91 130 5 ; ; PUNCT eurjchem-91 130 6     SPACE eurjchem-91 130 7 kim kim PROPN eurjchem-91 130 8 , , PUNCT eurjchem-91 130 9     SPACE eurjchem-91 130 10 y. y. NOUN eurjchem-91 130 11     SPACE eurjchem-91 130 12 r. r. PROPN eurjchem-91 130 13 ; ; PUNCT eurjchem-91 130 14     SPACE eurjchem-91 130 15 goulet goulet VERB eurjchem-91 130 16 , , PUNCT eurjchem-91 130 17     SPACE eurjchem-91 130 18 n. n. NOUN eurjchem-91 130 19     SPACE eurjchem-91 130 20 t. t. PROPN eurjchem-91 130 21 ; ; PUNCT eurjchem-91 130 22     SPACE eurjchem-91 130 23 boys boy NOUN eurjchem-91 130 24 , , PUNCT eurjchem-91 130 25     SPACE eurjchem-91 130 26 n. n. NOUN eurjchem-91 130 27 ; ; PUNCT eurjchem-91 130 28     SPACE eurjchem-91 130 29 hill hill NOUN eurjchem-91 130 30 , , PUNCT eurjchem-91 130 31     SPACE eurjchem-91 130 32 a. a. NOUN eurjchem-91 130 33     SPACE eurjchem-91 130 34 d. d. PROPN eurjchem-91 130 35 ; ; PUNCT eurjchem-91 130 36     SPACE eurjchem-91 130 37 kariv kariv PROPN eurjchem-91 130 38 , , PUNCT eurjchem-91 130 39     SPACE eurjchem-91 130 40 i. i. NOUN eurjchem-91 130 41 ; ; PUNCT eurjchem-91 130 42     SPACE eurjchem-91 130 43 krauss krauss PROPN eurjchem-91 130 44 , , PUNCT eurjchem-91 130 45     SPACE eurjchem-91 130 46 s. s. PROPN eurjchem-91 130 47 ; ; PUNCT eurjchem-91 130 48     SPACE eurjchem-91 130 49 ginanni ginanni NOUN eurjchem-91 130 50 , , PUNCT eurjchem-91 130 51     SPACE eurjchem-91 130 52 n. n. NOUN eurjchem-91 130 53 ; ; PUNCT eurjchem-91 130 54     SPACE eurjchem-91 130 55 stack stack NOUN eurjchem-91 130 56 , , PUNCT eurjchem-91 130 57     SPACE eurjchem-91 131 1 p. p. NOUN eurjchem-91 131 2     SPACE eurjchem-91 131 3 r. r. PROPN eurjchem-91 131 4 ; ; PUNCT eurjchem-91 131 5     SPACE eurjchem-91 131 6 kohli kohli PROPN eurjchem-91 131 7 , , PUNCT eurjchem-91 131 8     SPACE eurjchem-91 131 9 n. n. PROPN eurjchem-91 131 10     SPACE eurjchem-91 131 11 e. e. PROPN eurjchem-91 131 12 ; ; PUNCT eurjchem-91 131 13     SPACE eurjchem-91 131 14 chung chung PROPN eurjchem-91 131 15 , , PUNCT eurjchem-91 131 16     SPACE eurjchem-91 131 17 c. c. PROPN eurjchem-91 131 18     SPACE eurjchem-91 131 19 c. c. PROPN eurjchem-91 131 20 ; ; PUNCT eurjchem-91 131 21     SPACE eurjchem-91 131 22 varnerin varnerin NOUN eurjchem-91 131 23 , , PUNCT eurjchem-91 131 24     SPACE eurjchem-91 131 25 j. j. PROPN eurjchem-91 131 26     SPACE eurjchem-91 131 27 p. p. PROPN eurjchem-91 131 28 ; ; PUNCT eurjchem-91 131 29     SPACE eurjchem-91 131 30 goudreau goudreau NOUN eurjchem-91 131 31 , , PUNCT eurjchem-91 131 32     SPACE eurjchem-91 131 33 m. m. NOUN eurjchem-91 131 34     SPACE eurjchem-91 131 35 r. r. PROPN eurjchem-91 131 36 ; ; PUNCT eurjchem-91 131 37     SPACE eurjchem-91 131 38 mounot mounot NOUN eurjchem-91 131 39 , , PUNCT eurjchem-91 131 40     SPACE eurjchem-91 131 41 b. b. PROPN eurjchem-91 131 42     SPACE eurjchem-91 131 43 bioorg bioorg PROPN eurjchem-91 131 44 . . PUNCT eurjchem-91 131 45     SPACE eurjchem-91 132 1 med med PROPN eurjchem-91 132 2 . . PUNCT eurjchem-91 132 3     SPACE eurjchem-91 132 4 chem chem NOUN eurjchem-91 132 5 . . PUNCT eurjchem-91 132 6     SPACE eurjchem-91 133 1 lett lett PROPN eurjchem-91 133 2 . . PUNCT eurjchem-91 133 3     SPACE eurjchem-91 134 1 2006 2006 NUM eurjchem-91 134 2 , , PUNCT eurjchem-91 134 3     SPACE eurjchem-91 134 4 16 16 NUM eurjchem-91 134 5 , , PUNCT eurjchem-91 134 6     SPACE eurjchem-91 134 7 4620‐ 4620‐ NUM eurjchem-91 134 8 4623 4623 NUM eurjchem-91 134 9 .. .. PUNCT eurjchem-91 134 10     SPACE eurjchem-91 135 1 [ [ X eurjchem-91 135 2 7 7 NUM eurjchem-91 135 3 ] ] PUNCT eurjchem-91 135 4 . . PUNCT eurjchem-91 135 5 takagoki takagoki PROPN eurjchem-91 135 6 , , PUNCT eurjchem-91 135 7     SPACE eurjchem-91 135 8 s. s. PROPN eurjchem-91 135 9 ; ; PUNCT eurjchem-91 135 10     SPACE eurjchem-91 135 11 kimura kimura NOUN eurjchem-91 135 12 , , PUNCT eurjchem-91 135 13     SPACE eurjchem-91 135 14 n. n. NOUN eurjchem-91 135 15 ; ; PUNCT eurjchem-91 135 16     SPACE eurjchem-91 135 17 aoki aoki PROPN eurjchem-91 135 18 , , PUNCT eurjchem-91 135 19     SPACE eurjchem-91 135 20 y. y. NOUN eurjchem-91 135 21     SPACE eurjchem-91 135 22 i. i. PROPN eurjchem-91 135 23     SPACE eurjchem-91 135 24 m. m. PROPN eurjchem-91 135 25     SPACE eurjchem-91 135 26 jpn jpn PROPN eurjchem-91 135 27 . . PUNCT eurjchem-91 135 28     SPACE eurjchem-91 135 29 kokai kokai PROPN eurjchem-91 135 30     SPACE eurjchem-91 135 31 tokkyo tokkyo PROPN eurjchem-91 135 32     SPACE eurjchem-91 135 33 koha koha PROPN eurjchem-91 135 34     SPACE eurjchem-91 135 35 jp jp PROPN eurjchem-91 135 36     SPACE eurjchem-91 135 37 2005 2005 NUM eurjchem-91 135 38 , , PUNCT eurjchem-91 135 39     SPACE eurjchem-91 135 40 119 119 NUM eurjchem-91 135 41 , , PUNCT eurjchem-91 135 42     SPACE eurjchem-91 135 43 976‐976 976‐976 NOUN eurjchem-91 135 44 . . PUNCT eurjchem-91 135 45     SPACE eurjchem-91 136 1 [ [ X eurjchem-91 136 2 8 8 NUM eurjchem-91 136 3 ] ] PUNCT eurjchem-91 136 4 . . PUNCT eurjchem-91 137 1 katlinska katlinska PROPN eurjchem-91 137 2 , , PUNCT eurjchem-91 137 3     SPACE eurjchem-91 137 4 j. j. PROPN eurjchem-91 137 5     SPACE eurjchem-91 137 6 polish polish PROPN eurjchem-91 137 7     SPACE eurjchem-91 137 8 j. j. PROPN eurjchem-91 137 9     SPACE eurjchem-91 137 10 pharm pharm PROPN eurjchem-91 137 11 . . PUNCT eurjchem-91 137 12     SPACE eurjchem-91 137 13 2001 2001 NUM eurjchem-91 137 14 , , PUNCT eurjchem-91 137 15     SPACE eurjchem-91 137 16 53 53 NUM eurjchem-91 137 17 , , PUNCT eurjchem-91 137 18     SPACE eurjchem-91 137 19 47‐50 47‐50 NUM eurjchem-91 137 20 . . PUNCT eurjchem-91 137 21     SPACE eurjchem-91 138 1 [ [ X eurjchem-91 138 2 9 9 NUM eurjchem-91 138 3 ] ] PUNCT eurjchem-91 138 4 . . PUNCT eurjchem-91 139 1 abonίa abonίa PROPN eurjchem-91 139 2 , , PUNCT eurjchem-91 139 3     SPACE eurjchem-91 139 4 r. r. PROPN eurjchem-91 139 5 ; ; PUNCT eurjchem-91 139 6     SPACE eurjchem-91 139 7 cuervo cuervo PROPN eurjchem-91 139 8 , , PUNCT eurjchem-91 139 9     SPACE eurjchem-91 139 10 p. p. NOUN eurjchem-91 139 11 ; ; PUNCT eurjchem-91 139 12     SPACE eurjchem-91 139 13 hursthouse hursthouse NOUN eurjchem-91 139 14 , , PUNCT eurjchem-91 139 15     SPACE eurjchem-91 139 16 m. m. NOUN eurjchem-91 139 17     SPACE eurjchem-91 139 18 b. b. PROPN eurjchem-91 139 19 ; ; PUNCT eurjchem-91 139 20     SPACE eurjchem-91 139 21 cobo cobo PROPN eurjchem-91 139 22 , , PUNCT eurjchem-91 139 23     SPACE eurjchem-91 139 24 j. j. PROPN eurjchem-91 139 25 ; ; PUNCT eurjchem-91 139 26     SPACE eurjchem-91 139 27 glidewell glidewell NOUN eurjchem-91 139 28 , , PUNCT eurjchem-91 139 29     SPACE eurjchem-91 139 30 c. c. PROPN eurjchem-91 139 31     SPACE eurjchem-91 139 32 acta acta PROPN eurjchem-91 139 33     SPACE eurjchem-91 139 34 cryst cryst NOUN eurjchem-91 139 35 . . PUNCT eurjchem-91 139 36     SPACE eurjchem-91 139 37 sect sect NOUN eurjchem-91 139 38 . . PUNCT eurjchem-91 139 39     SPACE eurjchem-91 140 1 c c X eurjchem-91 140 2 : : PUNCT eurjchem-91 140 3     SPACE eurjchem-91 140 4 crystal crystal NOUN eurjchem-91 140 5     SPACE eurjchem-91 140 6 str str NOUN eurjchem-91 140 7 . . PUNCT eurjchem-91 140 8     SPACE eurjchem-91 140 9 commun commun PROPN eurjchem-91 140 10 . . PUNCT eurjchem-91 140 11     SPACE eurjchem-91 140 12 2010 2010 NUM eurjchem-91 140 13 , , PUNCT eurjchem-91 140 14     SPACE eurjchem-91 140 15 66 66 NUM eurjchem-91 140 16 , , PUNCT eurjchem-91 140 17     SPACE eurjchem-91 140 18 44‐46 44‐46 NUM eurjchem-91 140 19 . . PUNCT eurjchem-91 140 20     SPACE eurjchem-91 141 1 [ [ X eurjchem-91 141 2 10 10 NUM eurjchem-91 141 3 ] ] PUNCT eurjchem-91 141 4 . . PUNCT eurjchem-91 142 1 gao gao PROPN eurjchem-91 142 2 , , PUNCT eurjchem-91 142 3     SPACE eurjchem-91 142 4 w. w. PROPN eurjchem-91 142 5     SPACE eurjchem-91 142 6 t. t. PROPN eurjchem-91 142 7 ; ; PUNCT eurjchem-91 142 8     SPACE eurjchem-91 142 9 hou hou NOUN eurjchem-91 142 10 , , PUNCT eurjchem-91 142 11     SPACE eurjchem-91 142 12 w. w. PROPN eurjchem-91 142 13     SPACE eurjchem-91 142 14 d. d. PROPN eurjchem-91 142 15 ; ; PUNCT eurjchem-91 142 16     SPACE eurjchem-91 142 17 zheng zheng PROPN eurjchem-91 142 18 , , PUNCT eurjchem-91 142 19     SPACE eurjchem-91 142 20 m. m. NOUN eurjchem-91 142 21     SPACE eurjchem-91 142 22 r. r. PROPN eurjchem-91 142 23 ; ; PUNCT eurjchem-91 142 24     SPACE eurjchem-91 142 25 tang tang NOUN eurjchem-91 142 26 , , PUNCT eurjchem-91 142 27     SPACE eurjchem-91 142 28 l. l. PROPN eurjchem-91 142 29     SPACE eurjchem-91 142 30 j. j. PROPN eurjchem-91 142 31     SPACE eurjchem-91 142 32 synth synth NOUN eurjchem-91 142 33 . . PUNCT eurjchem-91 142 34     SPACE eurjchem-91 142 35 commun commun PROPN eurjchem-91 142 36 . . PUNCT eurjchem-91 142 37     SPACE eurjchem-91 142 38 2010 2010 NUM eurjchem-91 142 39 , , PUNCT eurjchem-91 142 40     SPACE eurjchem-91 142 41 40 40 NUM eurjchem-91 142 42 , , PUNCT eurjchem-91 142 43     SPACE eurjchem-91 142 44 732‐738 732‐738 PROPN eurjchem-91 142 45 . . PUNCT eurjchem-91 142 46     SPACE eurjchem-91 143 1 [ [ X eurjchem-91 143 2 11 11 NUM eurjchem-91 143 3 ] ] PUNCT eurjchem-91 143 4 . . PUNCT eurjchem-91 144 1 jampilek jampilek PROPN eurjchem-91 144 2 , , PUNCT eurjchem-91 144 3     SPACE eurjchem-91 144 4 j. j. PROPN eurjchem-91 144 5 ; ; PUNCT eurjchem-91 144 6     SPACE eurjchem-91 144 7 musiol musiol NOUN eurjchem-91 144 8 , , PUNCT eurjchem-91 144 9     SPACE eurjchem-91 144 10 r. r. PROPN eurjchem-91 144 11 ; ; PUNCT eurjchem-91 144 12     SPACE eurjchem-91 144 13 pesko pesko ADV eurjchem-91 144 14 , , PUNCT eurjchem-91 144 15     SPACE eurjchem-91 144 16 m. m. NOUN eurjchem-91 144 17 ; ; PUNCT eurjchem-91 144 18     SPACE eurjchem-91 144 19 kralova kralova PROPN eurjchem-91 144 20 , , PUNCT eurjchem-91 144 21     SPACE eurjchem-91 144 22 k. k. PROPN eurjchem-91 144 23 ; ; PUNCT eurjchem-91 144 24     SPACE eurjchem-91 144 25 vejsova vejsova PROPN eurjchem-91 144 26 , , PUNCT eurjchem-91 144 27     SPACE eurjchem-91 144 28 m. m. NOUN eurjchem-91 144 29 ; ; PUNCT eurjchem-91 144 30     SPACE eurjchem-91 144 31 carroll carroll NOUN eurjchem-91 144 32 , , PUNCT eurjchem-91 144 33     SPACE eurjchem-91 144 34 j. j. PROPN eurjchem-91 144 35 ; ; PUNCT eurjchem-91 144 36     SPACE eurjchem-91 144 37 coffey coffey NOUN eurjchem-91 144 38 , , PUNCT eurjchem-91 144 39     SPACE eurjchem-91 144 40 a. a. NOUN eurjchem-91 144 41 ; ; PUNCT eurjchem-91 144 42     SPACE eurjchem-91 144 43 dohnal dohnal ADJ eurjchem-91 144 44 , , PUNCT eurjchem-91 144 45     SPACE eurjchem-91 144 46 j. j. PROPN eurjchem-91 144 47     SPACE eurjchem-91 144 48 molecules molecule NOUN eurjchem-91 144 49     SPACE eurjchem-91 144 50 2009 2009 NUM eurjchem-91 144 51 , , PUNCT eurjchem-91 144 52     SPACE eurjchem-91 144 53 14 14 NUM eurjchem-91 144 54 , , PUNCT eurjchem-91 144 55     SPACE eurjchem-91 144 56 1145‐1159 1145‐1159 NUM eurjchem-91 144 57 . . PUNCT eurjchem-91 144 58     SPACE eurjchem-91 145 1 [ [ X eurjchem-91 145 2 12 12 NUM eurjchem-91 145 3 ] ] PUNCT eurjchem-91 145 4 . . PUNCT eurjchem-91 146 1 tedesco tedesco PROPN eurjchem-91 146 2 , , PUNCT eurjchem-91 146 3     SPACE eurjchem-91 146 4 r. r. PROPN eurjchem-91 146 5 ; ; PUNCT eurjchem-91 146 6     SPACE eurjchem-91 146 7 chai chai NOUN eurjchem-91 146 8 , , PUNCT eurjchem-91 146 9     SPACE eurjchem-91 146 10 d. d. PROPN eurjchem-91 146 11 ; ; PUNCT eurjchem-91 146 12     SPACE eurjchem-91 146 13 darcy darcy PROPN eurjchem-91 146 14 , , PUNCT eurjchem-91 146 15     SPACE eurjchem-91 146 16 m. m. NOUN eurjchem-91 146 17     SPACE eurjchem-91 146 18 g. g. PROPN eurjchem-91 146 19 ; ; PUNCT eurjchem-91 146 20     SPACE eurjchem-91 146 21 dhanak dhanak NOUN eurjchem-91 146 22 , , PUNCT eurjchem-91 146 23     SPACE eurjchem-91 146 24 d. d. PROPN eurjchem-91 146 25 ; ; PUNCT eurjchem-91 146 26     SPACE eurjchem-91 146 27 fitch fitch PROPN eurjchem-91 146 28 , , PUNCT eurjchem-91 146 29     SPACE eurjchem-91 146 30 d. d. PROPN eurjchem-91 146 31     SPACE eurjchem-91 146 32 m. m. NOUN eurjchem-91 146 33 ; ; PUNCT eurjchem-91 146 34     SPACE eurjchem-91 146 35 gates gate NOUN eurjchem-91 146 36 , , PUNCT eurjchem-91 146 37     SPACE eurjchem-91 146 38 a. a. NOUN eurjchem-91 146 39 ; ; PUNCT eurjchem-91 146 40     SPACE eurjchem-91 146 41 johnston johnston PROPN eurjchem-91 146 42 , , PUNCT eurjchem-91 146 43     SPACE eurjchem-91 146 44 v. v. ADP eurjchem-91 146 45     SPACE eurjchem-91 146 46 k. k. NOUN eurjchem-91 146 47 ; ; PUNCT eurjchem-91 146 48     SPACE eurjchem-91 146 49 duffy duffy PROPN eurjchem-91 146 50 , , PUNCT eurjchem-91 146 51     SPACE eurjchem-91 146 52 k. k. PROPN eurjchem-91 146 53     SPACE eurjchem-91 146 54 j. j. PROPN eurjchem-91 146 55     SPACE eurjchem-91 146 56 bioorg bioorg PROPN eurjchem-91 146 57 . . PUNCT eurjchem-91 146 58     SPACE eurjchem-91 146 59 med med PROPN eurjchem-91 146 60 . . PUNCT eurjchem-91 146 61     SPACE eurjchem-91 146 62 chem chem NOUN eurjchem-91 146 63 . . PUNCT eurjchem-91 146 64     SPACE eurjchem-91 147 1 lett lett PROPN eurjchem-91 147 2 . . PUNCT eurjchem-91 147 3     SPACE eurjchem-91 148 1 2009 2009 NUM eurjchem-91 148 2 , , PUNCT eurjchem-91 148 3     SPACE eurjchem-91 148 4 19 19 NUM eurjchem-91 148 5 , , PUNCT eurjchem-91 148 6     SPACE eurjchem-91 148 7 4354‐ 4354‐ NUM eurjchem-91 148 8 4358 4358 NUM eurjchem-91 148 9 . . PUNCT eurjchem-91 148 10     SPACE eurjchem-91 149 1 [ [ X eurjchem-91 149 2 13 13 NUM eurjchem-91 149 3 ] ] PUNCT eurjchem-91 149 4 . . PUNCT eurjchem-91 150 1 zhang zhang PROPN eurjchem-91 150 2 , , PUNCT eurjchem-91 150 3     SPACE eurjchem-91 150 4 s.‐l s.‐l PROPN eurjchem-91 150 5 . . PROPN eurjchem-91 150 6 ; ; PUNCT eurjchem-91 150 7     SPACE eurjchem-91 150 8 huang huang PROPN eurjchem-91 150 9 , , PUNCT eurjchem-91 150 10     SPACE eurjchem-91 150 11 z.‐s z.‐s NUM eurjchem-91 150 12 . . PUNCT eurjchem-91 150 13 ; ; PUNCT eurjchem-91 150 14     SPACE eurjchem-91 150 15 li li PROPN eurjchem-91 150 16 , , PUNCT eurjchem-91 150 17     SPACE eurjchem-91 150 18 y.‐m y.‐m NUM eurjchem-91 150 19 . . PUNCT eurjchem-91 150 20 ; ; PUNCT eurjchem-91 150 21     SPACE eurjchem-91 150 22 chan chan PROPN eurjchem-91 150 23 , , PUNCT eurjchem-91 150 24     SPACE eurjchem-91 150 25 a. a. NOUN eurjchem-91 150 26     SPACE eurjchem-91 150 27 s. s. PROPN eurjchem-91 150 28     SPACE eurjchem-91 150 29 c. c. PROPN eurjchem-91 150 30 ; ; PUNCT eurjchem-91 150 31     SPACE eurjchem-91 150 32 gu gu NOUN eurjchem-91 150 33 , , PUNCT eurjchem-91 150 34     SPACE eurjchem-91 150 35 l.‐q l.‐q PROPN eurjchem-91 150 36 . . PUNCT eurjchem-91 150 37     SPACE eurjchem-91 150 38 tetrahedron tetrahedron NOUN eurjchem-91 150 39     SPACE eurjchem-91 150 40 2008 2008 NUM eurjchem-91 150 41 , , PUNCT eurjchem-91 150 42     SPACE eurjchem-91 150 43 64 64 NUM eurjchem-91 150 44 , , PUNCT eurjchem-91 150 45     SPACE eurjchem-91 150 46 4403‐4407 4403‐4407 NUM eurjchem-91 150 47 . . PUNCT eurjchem-91 150 48     SPACE eurjchem-91 151 1 [ [ X eurjchem-91 151 2 14 14 NUM eurjchem-91 151 3 ] ] PUNCT eurjchem-91 151 4 . . PUNCT eurjchem-91 152 1 abass abass PROPN eurjchem-91 152 2 , , PUNCT eurjchem-91 152 3     SPACE eurjchem-91 152 4 m. m. NOUN eurjchem-91 152 5 ; ; PUNCT eurjchem-91 152 6     SPACE eurjchem-91 152 7 othman othman ADJ eurjchem-91 152 8 , , PUNCT eurjchem-91 152 9     SPACE eurjchem-91 152 10 e. e. PROPN eurjchem-91 152 11     SPACE eurjchem-91 152 12 s. s. PROPN eurjchem-91 152 13 ; ; PUNCT eurjchem-91 152 14     SPACE eurjchem-91 152 15 hassan hassan PROPN eurjchem-91 152 16 , , PUNCT eurjchem-91 152 17     SPACE eurjchem-91 152 18 a. a. NOUN eurjchem-91 152 19     SPACE eurjchem-91 152 20 synth synth NOUN eurjchem-91 152 21 . . PUNCT eurjchem-91 152 22     SPACE eurjchem-91 152 23 commun commun PROPN eurjchem-91 152 24 . . PUNCT eurjchem-91 152 25     SPACE eurjchem-91 152 26 2007 2007 NUM eurjchem-91 152 27 , , PUNCT eurjchem-91 152 28     SPACE eurjchem-91 152 29 37 37 NUM eurjchem-91 152 30 , , PUNCT eurjchem-91 152 31     SPACE eurjchem-91 152 32 607‐ 607‐ NOUN eurjchem-91 152 33 621 621 NUM eurjchem-91 152 34 . . PUNCT eurjchem-91 152 35       SPACE eurjchem-91 153 1 [ [ X eurjchem-91 153 2 15 15 NUM eurjchem-91 153 3 ] ] PUNCT eurjchem-91 153 4 . . PUNCT eurjchem-91 154 1 roschger roschger NOUN eurjchem-91 154 2 , , PUNCT eurjchem-91 154 3     SPACE eurjchem-91 154 4 p. p. NOUN eurjchem-91 154 5 ; ; PUNCT eurjchem-91 154 6     SPACE eurjchem-91 154 7 stadlbauer stadlbauer NOUN eurjchem-91 154 8 , , PUNCT eurjchem-91 154 9     SPACE eurjchem-91 154 10 w. w. PROPN eurjchem-91 154 11     SPACE eurjchem-91 154 12 liebigs liebig VERB eurjchem-91 154 13     SPACE eurjchem-91 154 14 ann ann PROPN eurjchem-91 154 15 . . PUNCT eurjchem-91 154 16     SPACE eurjchem-91 154 17 chem chem NOUN eurjchem-91 154 18 . . PUNCT eurjchem-91 154 19     SPACE eurjchem-91 154 20 1990 1990 NUM eurjchem-91 154 21 , , PUNCT eurjchem-91 154 22     SPACE eurjchem-91 154 23 13 13 NUM eurjchem-91 154 24 , , PUNCT eurjchem-91 154 25     SPACE eurjchem-91 154 26 821‐823 821‐823 NUM eurjchem-91 154 27 . . PUNCT eurjchem-91 154 28     SPACE eurjchem-91 155 1 [ [ X eurjchem-91 155 2 16 16 NUM eurjchem-91 155 3 ] ] PUNCT eurjchem-91 155 4 . . PUNCT eurjchem-91 156 1 bowman bowman PROPN eurjchem-91 156 2 , , PUNCT eurjchem-91 156 3     SPACE eurjchem-91 156 4 r. r. PROPN eurjchem-91 156 5     SPACE eurjchem-91 156 6 e. e. PROPN eurjchem-91 156 7 ; ; PUNCT eurjchem-91 156 8     SPACE eurjchem-91 156 9 campbell campbell PROPN eurjchem-91 156 10 , , PUNCT eurjchem-91 156 11     SPACE eurjchem-91 156 12 a. a. NOUN eurjchem-91 156 13 ; ; PUNCT eurjchem-91 156 14     SPACE eurjchem-91 156 15 tanner tanner NOUN eurjchem-91 156 16 , , PUNCT eurjchem-91 156 17     SPACE eurjchem-91 156 18 e. e. PROPN eurjchem-91 156 19     SPACE eurjchem-91 156 20 m. m. PROPN eurjchem-91 156 21     SPACE eurjchem-91 156 22 j. j. PROPN eurjchem-91 156 23     SPACE eurjchem-91 156 24 chem chem NOUN eurjchem-91 156 25 . . PUNCT eurjchem-91 156 26     SPACE eurjchem-91 156 27 soc soc PROPN eurjchem-91 156 28 . . PUNCT eurjchem-91 156 29     SPACE eurjchem-91 156 30 1959 1959 NUM eurjchem-91 156 31 , , PUNCT eurjchem-91 156 32     SPACE eurjchem-91 156 33 444‐ 444‐ NOUN eurjchem-91 156 34 447 447 NUM eurjchem-91 156 35 . . PUNCT eurjchem-91 156 36     SPACE eurjchem-91 157 1 [ [ X eurjchem-91 157 2 17 17 NUM eurjchem-91 157 3 ] ] PUNCT eurjchem-91 157 4 . . PUNCT eurjchem-91 158 1 stadlbauer stadlbauer PROPN eurjchem-91 158 2 , , PUNCT eurjchem-91 158 3     SPACE eurjchem-91 158 4 w. w. PROPN eurjchem-91 158 5 ; ; PUNCT eurjchem-91 158 6     SPACE eurjchem-91 158 7 kappe kappe PROPN eurjchem-91 158 8 , , PUNCT eurjchem-91 158 9     SPACE eurjchem-91 158 10 t. t. NOUN eurjchem-91 158 11     SPACE eurjchem-91 158 12 monatsh monatsh ADJ eurjchem-91 158 13 . . PUNCT eurjchem-91 158 14     SPACE eurjchem-91 158 15 chem chem NOUN eurjchem-91 158 16 . . PUNCT eurjchem-91 158 17     SPACE eurjchem-91 158 18 1985 1985 NUM eurjchem-91 158 19 , , PUNCT eurjchem-91 158 20     SPACE eurjchem-91 158 21 116 116 NUM eurjchem-91 158 22 , , PUNCT eurjchem-91 158 23     SPACE eurjchem-91 158 24 1005‐1015 1005‐1015 NUM eurjchem-91 158 25 . . PUNCT eurjchem-91 158 26       SPACE eurjchem-91 159 1 [ [ X eurjchem-91 159 2 18 18 NUM eurjchem-91 159 3 ] ] PUNCT eurjchem-91 159 4 . . PUNCT eurjchem-91 160 1 kappe kappe PROPN eurjchem-91 160 2 , , PUNCT eurjchem-91 160 3     SPACE eurjchem-91 160 4 t. t. PROPN eurjchem-91 160 5 ; ; PUNCT eurjchem-91 160 6     SPACE eurjchem-91 160 7 aigner aigner NOUN eurjchem-91 160 8 , , PUNCT eurjchem-91 160 9     SPACE eurjchem-91 160 10 r. r. PROPN eurjchem-91 160 11 ; ; PUNCT eurjchem-91 160 12     SPACE eurjchem-91 160 13 hohengassner hohengassner NOUN eurjchem-91 160 14 , , PUNCT eurjchem-91 160 15     SPACE eurjchem-91 160 16 p. p. NOUN eurjchem-91 160 17 ; ; PUNCT eurjchem-91 160 18     SPACE eurjchem-91 160 19 stadlbauer stadlbauer NOUN eurjchem-91 160 20 , , PUNCT eurjchem-91 160 21     SPACE eurjchem-91 160 22 w. w. PROPN eurjchem-91 160 23     SPACE eurjchem-91 160 24 j. j. PROPN eurjchem-91 160 25     SPACE eurjchem-91 160 26 prakt prakt NOUN eurjchem-91 160 27 . . PUNCT eurjchem-91 160 28     SPACE eurjchem-91 160 29 chem chem NOUN eurjchem-91 160 30 . . PUNCT eurjchem-91 160 31     SPACE eurjchem-91 160 32 chem.­ztg chem.­ztg PROPN eurjchem-91 160 33 . . PUNCT eurjchem-91 160 34     SPACE eurjchem-91 160 35 1994 1994 NUM eurjchem-91 160 36 , , PUNCT eurjchem-91 160 37     SPACE eurjchem-91 160 38 336 336 NUM eurjchem-91 160 39 , , PUNCT eurjchem-91 160 40     SPACE eurjchem-91 160 41 956‐961 956‐961 NUM eurjchem-91 160 42 . . PUNCT eurjchem-91 160 43     SPACE eurjchem-91 161 1 [ [ X eurjchem-91 161 2 19 19 NUM eurjchem-91 161 3 ] ] PUNCT eurjchem-91 161 4 . . PUNCT eurjchem-91 161 5 brown brown PROPN eurjchem-91 161 6 , , PUNCT eurjchem-91 161 7     SPACE eurjchem-91 161 8 r. r. PROPN eurjchem-91 161 9     SPACE eurjchem-91 161 10 f.c f.c PROPN eurjchem-91 161 11 . . PROPN eurjchem-91 161 12 ; ; PUNCT eurjchem-91 161 13     SPACE eurjchem-91 161 14 hobbs hobbs PROPN eurjchem-91 161 15 , , PUNCT eurjchem-91 161 16     SPACE eurjchem-91 161 17 j. j. PROPN eurjchem-91 161 18     SPACE eurjchem-91 161 19 j. j. PROPN eurjchem-91 161 20 ; ; PUNCT eurjchem-91 161 21     SPACE eurjchem-91 161 22 hughes hughe NOUN eurjchem-91 161 23 , , PUNCT eurjchem-91 161 24     SPACE eurjchem-91 161 25 g. g. PROPN eurjchem-91 161 26     SPACE eurjchem-91 161 27 k. k. PROPN eurjchem-91 161 28 ; ; PUNCT eurjchem-91 161 29     SPACE eurjchem-91 161 30 ritchie ritchie PROPN eurjchem-91 161 31 , , PUNCT eurjchem-91 161 32     SPACE eurjchem-91 161 33 e. e. PROPN eurjchem-91 161 34     SPACE eurjchem-91 161 35 aust aust PROPN eurjchem-91 161 36 . . PUNCT eurjchem-91 161 37     SPACE eurjchem-91 161 38 j. j. PROPN eurjchem-91 161 39     SPACE eurjchem-91 161 40 chem chem NOUN eurjchem-91 161 41 . . PUNCT eurjchem-91 161 42     SPACE eurjchem-91 161 43 1954 1954 NUM eurjchem-91 161 44 , , PUNCT eurjchem-91 161 45     SPACE eurjchem-91 161 46 7 7 NUM eurjchem-91 161 47 , , PUNCT eurjchem-91 161 48     SPACE eurjchem-91 161 49 348‐377 348‐377 NUM eurjchem-91 161 50 . . PUNCT eurjchem-91 161 51     SPACE eurjchem-91 162 1 [ [ X eurjchem-91 162 2 20 20 NUM eurjchem-91 162 3 ] ] PUNCT eurjchem-91 162 4 . . PUNCT eurjchem-91 162 5 ingalls ingall NOUN eurjchem-91 162 6 , , PUNCT eurjchem-91 162 7     SPACE eurjchem-91 162 8 e. e. PROPN eurjchem-91 162 9     SPACE eurjchem-91 162 10 a. a. PROPN eurjchem-91 162 11 ; ; PUNCT eurjchem-91 162 12     SPACE eurjchem-91 162 13 popp popp VERB eurjchem-91 162 14 , , PUNCT eurjchem-91 162 15     SPACE eurjchem-91 162 16 f. f. PROPN eurjchem-91 162 17     SPACE eurjchem-91 162 18 d. d. PROPN eurjchem-91 162 19     SPACE eurjchem-91 162 20 j. j. PROPN eurjchem-91 162 21     SPACE eurjchem-91 162 22 heterocycl heterocycl PROPN eurjchem-91 162 23 . . PUNCT eurjchem-91 162 24     SPACE eurjchem-91 162 25 chem chem NOUN eurjchem-91 162 26 . . PUNCT eurjchem-91 162 27     SPACE eurjchem-91 163 1 1967 1967 NUM eurjchem-91 163 2 , , PUNCT eurjchem-91 163 3     SPACE eurjchem-91 163 4 4 4 NUM eurjchem-91 163 5 , , PUNCT eurjchem-91 163 6     SPACE eurjchem-91 163 7 523–526 523–526 NUM eurjchem-91 163 8 . . PUNCT eurjchem-91 163 9       SPACE eurjchem-91 164 1 [ [ X eurjchem-91 164 2 21 21 NUM eurjchem-91 164 3 ] ] PUNCT eurjchem-91 164 4 . . PUNCT eurjchem-91 165 1 petersen petersen PROPN eurjchem-91 165 2 , , PUNCT eurjchem-91 165 3     SPACE eurjchem-91 165 4 u. u. PROPN eurjchem-91 165 5 ; ; PUNCT eurjchem-91 165 6     SPACE eurjchem-91 165 7 heitzer heitzer NOUN eurjchem-91 165 8 , , PUNCT eurjchem-91 165 9     SPACE eurjchem-91 165 10 h. h. PROPN eurjchem-91 165 11     SPACE eurjchem-91 165 12 liebigs liebig VERB eurjchem-91 165 13     SPACE eurjchem-91 165 14 ann ann PROPN eurjchem-91 165 15 . . PUNCT eurjchem-91 165 16     SPACE eurjchem-91 165 17 chem chem NOUN eurjchem-91 165 18 . . PUNCT eurjchem-91 165 19     SPACE eurjchem-91 165 20 1976 1976 NUM eurjchem-91 165 21 , , PUNCT eurjchem-91 165 22     SPACE eurjchem-91 165 23 9 9 NUM eurjchem-91 165 24 , , PUNCT eurjchem-91 165 25     SPACE eurjchem-91 165 26 1659‐1662 1659‐1662 NUM eurjchem-91 165 27 . . PUNCT eurjchem-91 165 28     SPACE eurjchem-91 166 1 [ [ X eurjchem-91 166 2 22 22 NUM eurjchem-91 166 3 ] ] PUNCT eurjchem-91 166 4 . . PUNCT eurjchem-91 167 1 ibrahim ibrahim PROPN eurjchem-91 167 2 , , PUNCT eurjchem-91 167 3     SPACE eurjchem-91 167 4 s. s. PROPN eurjchem-91 167 5     SPACE eurjchem-91 167 6 s. s. PROPN eurjchem-91 167 7 ; ; PUNCT eurjchem-91 167 8     SPACE eurjchem-91 167 9 allimony allimony ADJ eurjchem-91 167 10 , , PUNCT eurjchem-91 167 11     SPACE eurjchem-91 167 12 h. h. PROPN eurjchem-91 167 13     SPACE eurjchem-91 167 14 a. a. NOUN eurjchem-91 167 15 ; ; PUNCT eurjchem-91 167 16     SPACE eurjchem-91 167 17 abdel‐halim abdel‐halim PROPN eurjchem-91 167 18 , , PUNCT eurjchem-91 167 19     SPACE eurjchem-91 167 20 a. a. NOUN eurjchem-91 167 21     SPACE eurjchem-91 167 22 m. m. NOUN eurjchem-91 167 23 ; ; PUNCT eurjchem-91 167 24     SPACE eurjchem-91 167 25 ibrahim ibrahim NOUN eurjchem-91 167 26 , , PUNCT eurjchem-91 167 27     SPACE eurjchem-91 167 28 m. m. NOUN eurjchem-91 167 29     SPACE eurjchem-91 167 30 a. a. NOUN eurjchem-91 167 31     SPACE eurjchem-91 167 32 arkivoc arkivoc NOUN eurjchem-91 167 33     SPACE eurjchem-91 167 34 2009 2009 NUM eurjchem-91 167 35 , , PUNCT eurjchem-91 167 36     SPACE eurjchem-91 167 37 14 14 NUM eurjchem-91 167 38 , , PUNCT eurjchem-91 167 39     SPACE eurjchem-91 167 40 28‐38 28‐38 NOUN eurjchem-91 167 41 . . PUNCT eurjchem-91 167 42       SPACE eurjchem-91 168 1 [ [ X eurjchem-91 168 2 23 23 NUM eurjchem-91 168 3 ] ] PUNCT eurjchem-91 168 4 . . PUNCT eurjchem-91 169 1 ibrahim ibrahim PROPN eurjchem-91 169 2 , , PUNCT eurjchem-91 169 3     SPACE eurjchem-91 169 4 m. m. NOUN eurjchem-91 169 5     SPACE eurjchem-91 169 6 a. a. NOUN eurjchem-91 169 7     SPACE eurjchem-91 169 8 synth synth NOUN eurjchem-91 169 9 . . PUNCT eurjchem-91 169 10     SPACE eurjchem-91 169 11 commun commun PROPN eurjchem-91 169 12 . . PUNCT eurjchem-91 169 13     SPACE eurjchem-91 169 14 2009 2009 NUM eurjchem-91 169 15 , , PUNCT eurjchem-91 169 16     SPACE eurjchem-91 169 17 39 39 NUM eurjchem-91 169 18 , , PUNCT eurjchem-91 169 19     SPACE eurjchem-91 169 20 3527‐3545 3527‐3545 NUM eurjchem-91 169 21 . . PUNCT eurjchem-91 169 22       SPACE eurjchem-91 170 1 [ [ X eurjchem-91 170 2 24 24 NUM eurjchem-91 170 3 ] ] PUNCT eurjchem-91 170 4 . . PUNCT eurjchem-91 171 1 rashid rashid PROPN eurjchem-91 171 2 , , PUNCT eurjchem-91 171 3     SPACE eurjchem-91 171 4 m. m. NOUN eurjchem-91 171 5     SPACE eurjchem-91 171 6 a. a. NOUN eurjchem-91 171 7 ; ; PUNCT eurjchem-91 171 8     SPACE eurjchem-91 171 9 rasool rasool NOUN eurjchem-91 171 10 , , PUNCT eurjchem-91 171 11     SPACE eurjchem-91 171 12 n. n. NOUN eurjchem-91 171 13 ; ; PUNCT eurjchem-91 171 14     SPACE eurjchem-91 171 15 appel appel PROPN eurjchem-91 171 16 , , PUNCT eurjchem-91 171 17     SPACE eurjchem-91 171 18 b. b. PROPN eurjchem-91 171 19 ; ; PUNCT eurjchem-91 171 20     SPACE eurjchem-91 171 21 adeel adeel PROPN eurjchem-91 171 22 , , PUNCT eurjchem-91 171 23     SPACE eurjchem-91 171 24 m. m. NOUN eurjchem-91 171 25 ; ; PUNCT eurjchem-91 171 26     SPACE eurjchem-91 171 27 karapetyan karapetyan PROPN eurjchem-91 171 28 , , PUNCT eurjchem-91 171 29     SPACE eurjchem-91 171 30 v. v. ADV eurjchem-91 171 31 ; ; PUNCT eurjchem-91 171 32     SPACE eurjchem-91 171 33 mkrtchyan mkrtchyan ADJ eurjchem-91 171 34 , , PUNCT eurjchem-91 171 35     SPACE eurjchem-91 171 36 s. s. PROPN eurjchem-91 171 37 ; ; PUNCT eurjchem-91 171 38     SPACE eurjchem-91 171 39 reinke reinke NOUN eurjchem-91 171 40 , , PUNCT eurjchem-91 171 41     SPACE eurjchem-91 171 42 h. h. PROPN eurjchem-91 171 43 ; ; PUNCT eurjchem-91 171 44     SPACE eurjchem-91 171 45 fischer fischer NOUN eurjchem-91 171 46 , , PUNCT eurjchem-91 171 47     SPACE eurjchem-91 171 48 c. c. NOUN eurjchem-91 171 49 ; ; PUNCT eurjchem-91 171 50     SPACE eurjchem-91 171 51 langer langer NOUN eurjchem-91 171 52 , , PUNCT eurjchem-91 171 53     SPACE eurjchem-91 171 54 p. p. NOUN eurjchem-91 171 55     SPACE eurjchem-91 171 56 tetrahedron tetrahedron NOUN eurjchem-91 171 57     SPACE eurjchem-91 171 58 2008 2008 NUM eurjchem-91 171 59 , , PUNCT eurjchem-91 171 60     SPACE eurjchem-91 171 61 64 64 NUM eurjchem-91 171 62 , , PUNCT eurjchem-91 171 63     SPACE eurjchem-91 171 64 5416‐5425 5416‐5425 NUM eurjchem-91 171 65 . . PUNCT eurjchem-91 171 66     SPACE