id	author	title	date	pages	extension	mime	words	sentence	flesch	summary	cache	txt
eurjchem-351	Abass, Mohamed; Mohamed, Elhossain Ali; Ismail, Mostafa Mohamed; Mayas, Aisha Saleh	Substituted Quinolinones. Part 16. Preparation and reactions of 3-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-3-oxopropanoic acid	2011	10	.pdf	application/pdf	6375	270	62	Compound No. IR (KBr),  (cm‐1) 1H NMR (DMSO‐d6) †,  Mass, m/z (Ir%) 2 3447‐2951 (OH), 1734 (C=Ocarboxylic), 1672 (C=Oketone), 1615 (C=Oquinolone) (CDCl3): 3.79 (s, 3H, NCH3), 3.88 (s, 2H, CH2), 5.66 (s, 0.5H, 3‐H), 7.26 (d, 1H, J = 8, 8‐H), 7.50 (dd, 1H, J = 7.8, 2.0, 6‐H), 7.80 (dd, 1H, J = 7.8, 2.0, 7‐H), 8.32 (d, 1H, J = 8, 5‐H), 13.60 (bs, 0.5H, OH), 15.60 (bs, 1H, OHcarboxylic) 261 (4.1) (M+̣), 243 (M+̣ ‐ H2O) (22.8), 245 (3.6), 244 (8.4), 217 (23.3), 215 (100), 216 (17.6), 131 (32.4), 106 (11.3), 89 (37.3), 76 (26.3), 65 (22.7), 53 (39.4), 50 (44.2) 3a 3444 (OH), 1735 (C=Oester), 1672 (C=Oketone), 1644 (C=Oquinolone), 1162 (C‐O‐Cether) 3.48 (s, 3H, NCH3), 3.52 (s, 2H, CH2), 3.62 (s, 3H, OCH3), 7.44 (t, 1H, J = 6.2, 6‐ H), 7.64 (d, 1H, J = 8, 8‐ H), 7.76 (t, 1H, J = 6.2, 7‐H), 8 (d, 1H, J = 8, 5‐H), 13.4 (bs, 1H, OH) 275 (4.8) (M+̣), 276 (1.5), 274(1.9), 261 (9.6), 245 (18.3), 217 (12.4), 203 (13.8), 175 (100), 161 (17.6), 145 (24.4), 117 (16.2), 93 (28.1), 77 (23.2), 64 (16.0), 51 (45.0) 4 3446‐ 2500 (OH, NH), 1739 (C=Ocarboxylic), 1671 (C=Oketone + C=Oquinolone) 3.50 (s, 3H, NCH3), 7.52 ( t, 1 H, J = 6.4, C7‐H), 7.79 (d, 1H, J = 8, C8‐H), 7.90 (t, 1H, J = 6.4,C6‐ H), 8 (d, 1H, J = 8, C5‐H), 12.8 (bs, 1H, OHoxime), 13.4 (bs, 1H, OH), 17.6 (bs, 1H, OHcarboxylic) 290 (M+̣) (4.9), 291 (1.3), 285 (15.4), 229 (5.4), 228 (13.6), 216 (23.0), 215 (40.3), 202 (18.1), 134 (18.5), 106 (15.7), 77 (75.9), 51 (100) 5 3432 (OH), 1737 (C=O pyrone), 1649 (C=Oquinolone), 1618 (C=N) 3.50 (s, 3H, NCH3), 7.25‐7.32 (t, J = 6.9 Hz, 1H, 7‐H), 7.45 (d, J = 8.0 Hz, 1H, 8‐H), 7.76 (t, J = 6.9 Hz, 1H, 6‐H), 7.98 (d, J = 8.0 Hz, 1H, 5‐H), 12.8 (s, 1H, OHoxime) 6 3206‐2434 (OHcarboxylic), 1737 (C=Ocarboxlic), 1640 (C=Oquinolone), 1503, 1481 (NO2) 3.73 (s, 3H, NCH3), 7.30‐8.05 (m, 8H, Harom), 9.17 (bs, 1H, NH), 12.37 (bs, 1H, OH), 15.23 (bs, 1H, OHcarboxylic) 410 (M+̣) (5.1), 411(2.3), 394 (20.4), 365 (10.7), 349 (17.9), 321 (32.6), 230 (100), 217 (34.7), 203 (31.8), 175 (56.9) 7 3404(NH), 1725 ‐1673 (C=Opyrone), 1631 (C=O quinolone), 1571, 1495 (NO2) 3.73 (s, 3H, NCH3), 7.33‐8.02 (m, 8H, Harom), 9.40 (bs, 1H, NH) 392 (M+̣) (3.6), 393 (1.8), 347 (8.7), 256 (18.0), 243 (100), 230 (10.4), 217 (40.1), 203 (30.2), 189 (63.3), 175 (34.2), 161 (32.0) 8 3227 (OH, NH), 1742 (C=Ocarboxylic), 1674 (C=Oquinolone) 3.28 (s, 3H, NCH3), 3.63 (s, 3H, OCH3), 6.89 (d, 1H, J = 8.2, 2‐Hpyrrole), 7.09 (d, 1H, J = 8.2, 3‐HPyrrole), 7.51 (t, 1H, J = 7.9, 6‐H), 7.82 (m, 2H, 7‐H + 8‐H), 8.10 (d, 1H, J = 7.8, 5‐H), 9.64 (bs, 1H, NH), 13.8 (bs, 1H, OHcarboxylic) 298 (M+̣) (15.9), 299 (5.0), 297 (8.4), 283 (2.9), 269 (8.5), 267 (15.2), 266 (12.0), 254 (21.2), 215 (20.3), 199 (12.2), 159 (14.5), 131 (11.0), 77 (21.1), 76 (18.6), 75 (100) 10 3429, 3243 (OH, NH), 1740 (C=Ocarboxylic), 1730 (C=Oindolone), 1650 (C=Oquinolone) 3.71 (s, 3H, NCH3), 6.92‐8.34 (m, 8H, Harom), 10.42 (bs, 1H, NH), 12.40 (bs, 1H, OH), 14.2 (bs, 1H, OHcarboxylic) 390 (M+̣) (8.6), 391 (2.6), 346 (34.0), 330 (22.1), 316 (20.2), 173 (34.6), 159 (43.8), 145 (32.7) 11 3157 (NH), 1752 (C=Opyrone), 1652 (C=Oindolone, C=Oquinolone) 3.52 (s, 3H, NCH3), 7.04‐8.70 (m, 8H, Harom), 12.01 (bs, 1H, NH) 372 (M+̣) (4.6), 373 (1.7), 331 (23.3), 317(12.5), 255 (100), 241 (10.7), 229 (21.9), 201 (13.3), 200 (15.2), 173 (18.6), 145 (20.2), 78 (21.3) 12 3435 (OH), 1730 (C=Opyrone), 1636 (C=O quinolone) 3.49 (s, 3H, NCH3), 7.37‐7.84 (s, 8H, Harom), 8.16 (s, 1H, 4‐Hcoumarin), 14.80 (bs,1H, OH) 347 (M+̣) (100), 348 (36.0), 349 (6.7), 319 (39.6), 275 (61.9), 202 (38.4), 173 (57.6), 134 (46.5), 90 (23.6), 77 (71.4), 63 (46.8) 13 3423,(OH), 1670, 1651 (C=Opyrone), 1644 (C=Oquinolone) 3.52 (s, 3H, NCH3), 7.15‐7.97 (m, 8H, Harom), 5.68 (s, 1H, Hmethine), 12.00 (bs, 1H, OH) 17a 3415 (OH), 1717 (C=Opyrone), 1670 (C=Oquinolone) 3.70 (s, 3H, NCH3), 3.77 (s, 3H, NCH3), 5.82 (s, 1H, Hmethine), 7.30‐8.33 (m, 8H, Harom), 13.4 (bs, 1H, OH) 428 (M+̣) (38.3), 429 (9.4), 400 (31.2), 399(10.9), 385(6.8), 268(16.4), 254 (29.6), 226 (8.3), 214 (11.3), 202 (20.4), 199 (60.6), 172 (14.3), 117 (14.2), 115 (24.0), 104 (38.5), 77 (100), 76 (29.7), 64 (23.3) 17b 3438, 3158 (OH), 1752 (C=Opyrone), 1657 (C=Oquinolone) 2.43 (s, 3H, 6CH3), 3.49 (s, 3H, NCH3), 5.44 (s, 1H, Hmethine), 7.31‐8.05 (m, 7H, Harom), 12.11 (bs, 1H, NH), 13.8 (bs, 1H, OH) 428 (M+̣) (100), 429 (25.3), 430 (10.6), 427 (11.3), 400 (74.2), 399 (18.2), 372 (27.3), 226 (21.4), 200 (25.4), 199 (97.6), 186 (22.6), 39 (12.8), 104 (55.6), 77 (99.9) 20 3051 (C‐Harom), 1748 (C=Opyrone), 1644 (C=Opyrone), 1622 (C=Oquinolone) (CDCl3) 3.84 (s, 3H, NCH3), 6.94 (s, 1H, Hmethine), 7.12 (d, 1H, J = 7.9, 6‐Hquinolinone), 7.44 ‐7.53 (m, 4H, Harom), 7.74 (d, 1H, J = 8.2, 8‐Hchromone), 8.17 (d, 1H, J = 8.0, 5‐Hquinolone), 8.37 (d, 1H, J = 8.2, 5‐Hchromone), 8.70 (s, 1H, 2‐Hchromone) 399 (M+̣) (5.4), 400 (2.2), 398 (25.4), 397 (100), 396 (35.8), 368 (30.4), 277 (81.6), 276 (18.3), 104 (11.4), 93 (28.2), 77 (36.2), 65 (67.2) † All 1H NMR experiments were carried out in DMSO‐d6 unless cited. IR spectrum of the product showed a medium absorption band broaden between 3206‐2434 cm‐1 due to H‐ bonded N‐H and O‐H, in addition to two strong stretching bands at 1737 and 1640 cm‐1 due to C=O of carboxylic acid and quinolinone.	cache/eurjchem-351.pdf	txt/eurjchem-351.txt