Synthesis of some nitrogen heterocycles and their in vitro evaluation
(41.20), 101 (52.90), 91 (41.20), 85 (41.20), 83 (41.20), 76 (52.90), 69 (41.20), 67
(58.80), 66 (47.10), 65 (70.60), 60 (100), 58 (76.50), 57 (52.90), 55 (76.50), 50
(5.90). Anal. Found: C, 58.51; H, 4.06; N, 11.35. C12H10N2O4 requires: C, 58.54; H,
4.06; N, 11.38.
6-Aryl-5-cyano-4-hydroxy-2-substituted pyrimidines (3a and 5)
5-Bromo-2-hydroxybenzaldehyde thiosemicarbazone (9)
A mixture of 2a, b and thiourea, guanidine hydrochloride, and thiosemicarbazide
(0.01) in presence of anhydrous potassium carbonate (0.03 mol) in methanol
(50 ml) was heated under reflux for 2–3 h, then cooled and poured into dilute
hydrochloric acid (1 %). The solid formed was filtered off, washed with water,
dried, and purified by recrystallization from suitable solvent to give 3a, 5, and 9.
6-(5-Bromo-2-hydroxyphenyl)-5-cyano-4-hydroxy-2-mercaptopyrimidine (3a) as
pale yellow crystals, yield 68 %, m.p. 286 °C. IR (KBr): 3,390–2,850 (br-OH),
2,250 (CN), 1,635 (C=N), 1,618, 1,585 (C=C), 1,385 (C=S), 1,210, 1,083 (C–O)
1
cm-1. H-NMR (DMSO-d6): d 7.31–8.01 (m, 3H, Ar–H), 10.4 (s, 1H, NH), 11.30
(s, 1H, OH), 11.51 (s, 1H, OH) ppm. MS: m/z (%) = 325 (M??2, 83.60), 324
(M??1, 100), 323 (M?, 84.40), 310 (15.60), 309 (13.30), 308 (10.40), 307 (16.50),
297 (31.10), 296 (13.30), 293 (11.10), 292 (17.60), 291 (14.40), 290 (13.30), 269
(0.7), 268 (48.90), 267 (34.10), 266 (51.1), 265 (65.8), 264 (13.3), 239 (9.80), 238
(7.40), 237 (13.30), 94 (13.30), 93 (10.40), 90 (11.90), 89 (27.30), 86 (33.30), 85
(23.80), 82 (25.90), 81 (18.50), 80 (21.10), 79 (14.80), 71 (18.50), 69 (23.00), 68
(25.20), 64 (23.00), 63 (20.70), 61 (15.80), 60 (23.00), 59 (26.30), 58 (10.40), 56
(17.00), 53 (12.60), 52 (20.70), 50 (17.00). Anal. Found: C, 40.84; H, 1.83; N,
12.89; S, 9.89. C11H6N3BrO2S requires: C, 40.87; H, 1,86; N, 13.00; S, 9.91.
6-(3-nitrophenyl)-5-cyano-4-hydroxy-2-mercaptopyrimidine (3b) as yellow crys-
tals, yield 72 %, m.p. 278 °C. IR (KBr): 3,233 (NH), 3,390–2,850 (br.OH), 2,251
(CN), 1,631 (C=N), 1,617, 1,585 (C=C), 1,123 (C–O) cm-1. 1H-NMR (DMSO-d6):
d 7.31–8.15 (m, 4H, Ar–H), 10.21 (br-s, 1H, NH), 11.21 (s, 1H, OH) ppm. MS:
m/z (%) = 275 (M?1?1, 20.00), 274 (M?,23.00), 217 (12.50), 216 (30.00), 176
(50.00), 175 (95.00), 174 (52.50), 167 (17.50), 166 (47.50), 154 (17.50), 153
(12.30), 152 (15.00), 151 (22.50), 146 (30.00), 145 (32.50), 144 (25.00), 136 (100),
135 (42.50), 131 (22.50), 130 (20.00), 129 (60.00), 128 (77.50), 127 (37.50), 120
(20.00), 119 (90.00), 118 (52.50), 116 (57.50), 113 (37.50), 112 (15.00), 105
(30.00), 104 (22.50), 103 (70.00), 102 (55.00), 101 (47.50), 98 (40.00), 97 (22.50),
92 (12.50), 91 (67.50), 90 (62.50), 89 (52.50), 87 (25.00), 84 (32.50), 82 (22.50), 77
(82.50), 75 (42.50), 74 (32.50), 73 (35.00), 71 (40.00), 70 (40.00), 69 (65.00), 65
(40.00), 64 (52.50), 63 (80.00), 62 (27.50), 51 (47.50), 50 (65.00). Anal. Found: C,
48.03; H, 2.17; N, 20.35; S, 11.63. C11H6N4O3S requires: C, 48.17; H, 2.19; N,
20.44; S, 11.68.
6-(3-nitrophenyl)-5-cyano-4-hydroxy-2-aminopyrimidine (5) as pale yellow,
yield 63 %, m.p. 260 °C. IR (KBr): 3,385–2,875 (br.OH), 3,289, 3,171 (NH2),
2,255 (CN), 1,635 (C=N), 1,613, 1,589 (C=C), 1,172 (C–O) cm-1 1H-NMR
.
(DMSO-d6): d 6.21 (s, 2H, NH2), 7.31–8.10 (m, 4H, Ar–H), 11.23 (br-S, IH, OH)
123