Journal of Chemistry

Research Article

Synthesis and Antimicrobial Activities of Some New Heterocyclic Compounds Based on 6-Chloropyridazine-3(2H)-thione

Table 3

Spectral data of compounds (2–13).
Comp.IR cm−1 1H NMR ppm 13C-NMR ppm
2a3380 (NH), 1750 (CO), 1610 (C=N), 1459 (N–C=S), 1405 (C=S). 6.1 (s, 1H, NH, exchangeable with D2O), 6.9–7.6 (m, 6Ar H)126.72 (C6, C9), 127.45 (C8), 130.12 (C4), 130.48 (C3), 134.76 (C7), 154 (C2), 162 (C=O).
2b3410 (NH), 1620 (CO), 1595 (C=N), 1451 (N–C=S), 1411 (C=S).6.4 (s, 1H, NH, exchangeable with D2O), 7.4–7.9 (m, 4H Ar H)114 (C6), 123 (C8), 131.2 (C4), 131.6 (C3), 1349 (C9), 139.9 (C7), 154 (C2), 162 (C=O).
2c3385 (NH), 1616 (CO), 1580 (C=N), 1432 (N–C=S), 1418 (C=S).6.6 (s, 1H, NH, exchangeable with D2O), 7.1–7.8 (m, 5H, Ar H)122 (C8), 125 (C6), 131 (C4), 131.8 (C3), 133 (C9), 138 (C7), 153.4 (C2),
162.3 (C=O).
33370 (NH), 1610 (C=N), 1438 (N–C=S), 1401 (C=S). 6.7 (s, 1H, NH, exchangeable with D2O), 6.8–7.6 (m, 6H, Ar H).110.3 (C7), 112.1 (C10), 121.2 (C4), 123 (C8), 123 (C9), 125.2 (C5), 180.6 (C3).
43420 (NH), 3390 (NH), 1610 (C=N), 1432 (N–C=S), 1416 (C=S).6.3 (s, 1H, NH, exchangeable with D2O), 6.8 (s, 1H, NH, exchangeable with D2O), 6.9–7.6 (m, 6H, Ar H). 116.8 (C5 & C8 benzotriazine), 120.4 (C6 & C7, benzotriazine), 132.4 (C4, pyridazine), 134.1-(C5, pyridazine), 151 (C6), 154.1 (C3).
53310 (NH), 1660 (CO), 1605 (C=N), 1440 (N–C=S), 1413 (C=S).2.95 (d, 1H, −CH2), 3.15 (d, 1H, −CH2), 3.85 (d, 1H, −CH), 6.83 (s, 1H, NH, exchangeable with D2O), 7.41–7.96 (m, 7H, Ar H).40.1 (CH2), 72.4 (C4, imidazole), 125.1, 127.3, 128 (Ph–C), 130 (C5, pyridazine), 131.3 (C4, pyridazine), 152.3 (C6, pyridazine), 154.2 (C3, pyridazine), 174.2 (C=O).
63427-3409 (NH2), 3316 (NH), 1580 (C=N), 1444 (NC=S), 1408 (C=S).6.29 (s, 2H, NH2, exchangeable with D2O), 6.45 (s, 1H, NH), 6.81–6.93 (m, 2H, Ar H).122.1 (C4, pyridazine), 125.3 (C5, pyridazine), 137.9 (C3, triazole), 141.6 (C6, pyridazine), 179.3 (C3, p-yridazine).
7a3357 (NH), 1600 (C=N), 1425 (N–C=S), 1405 (C=S).6.52 (s, 1H, NH, exchangeable with D2O), 6.81–7.84 (m, 6H, Ar H).119.9 (C4, pyridazine), 122.2 (C5, pyridazine), 126.1 (C1, phenyl), 126.7 (C2 & C6, phenyl), 129.1 (C3 & C5, phenyl), 132.4 (C–Cl), 179.1 (C3, pyridazine).
7b3349 (NH), 1606 (C=N), 1432 (N–C=S), 1418 (C=S).6.48 (s, 1H, NH, exchangeable with D2O), 6.76–7.59 (m, 7H, Ar H).120.1 (C4, pyridazine), 122.5 (C5, pyridazine), 127.2 (C2 & C6, phenyl) 129.2 (C3 & C5, phenyl), 130.6 (C1, phenyl), 130.9 (C4, phenyl), 139.8 (C3, triazole), 180.1 (C3, pyridazine)
8a3420 (NH), 3391 (NH), 1610 (C=N), 1429 (N–C=S), 1408 (C=S).2.14 (s, 3H, CH3), 6.42 (s, 1H, NH, exchangeable with D2O), 6.9–7.7 (m, 7H, Ar H), 10.14 (s, 1H, NH, exchangeable with D2O). 25.4 (CH3), 81.5 (C3, triazole), 126 (C4, phenyl), 126.9 (C2 & C6, phenyl), 128 (C3 & C5, phenyl), 129.8 (C4, pyridazine), 134.2 (C5, pyridazine), 141.2 (C1, phenyl), 150.1 (C3, pyridazine).
8b3406 (NH), 3360 (NH), 1590 (C=N), 1437 (N–C=S), 1410 (C=S). 2.23 (s, 3H, CH3), 6.56 (s, 1H, NH, D2O-exchangeable), 6.8–7.7 (m, 6H, Ar H), 10.67 (s, 1H, NH, exchangeable with D2O).25.8 (CH3), 83.2 (C3, triazole), 122 (C4, phenyl), 123.5 (C2, phenyl), 129.1 (C5, phenyl), 129.8 (C4, pyridazine), 131.2 (C4, pyridazine), 133.2 (C6, phenyl), 136.2 (C5, pyridazine), 143.2 (C1, phenyl), 148.2 (C–NO2), 152.3 (C3, pyridazine).
93360 (NH), 1572 (C=N), 1417 (C=S), 1345 (S=O).2.99 (s, 3H, CH3), 6.5 (s, 1H, NH, exchangeable with D2O), 6.89–7.92 (m, 6H, Ar H).22.1 (CH3), 123.3 (C1, phenyl), 128.1 (C3 & C5, phenyl), 129.2 (C5, pyridazine), 129.8 (C4, pyridazine), 130.4 (C2 & C6, phenyl), 132.6 (C4, phenyl), 154.1 (C3, pyridazine).
101605 (C=N), 1530-1380 (NO2), 1340 (C–S–).7.9 (d, 1H, CH), 8.1 (d, 1H, CH), 8.58–8.62 (m, 2H, (NO2)2C6H3–), 9.08 (s, 1H, (NO2)2C6H3–),123.6 (C5, pyridazine), 124.8 (C3, phenyl), 129.1 (C5, phenyl), 129.3 (C4, pyridazine), 143.2 (C4, phenyl), 145.9 (C2, phenyl), 152.2 (C–Cl), 178.2 (C6, pyridazine).
111620 (C=N)7.9 (d, 2H, 2CH), 8.0 (d, 2H, 2CH)124.2 (2C5), 125.4 (2C4), 152.2 (2C–Cl), 178.1 (2C6).
123340 (NH), 1600 (C=N), 1273 (C–S–).6.35 (s, 1H, NH, exchangeable with D2O), 6.81–7.98 (m, 7H, Ar H).120.3 (C4 & C5, pyridazine), 122.5 (C4, phenyl), 127.1 (C2 & C6, phenyl), 128.2 (C3 & C5, phenyl), 134.2 (C1, phenyl), 177.2 (2C–S).
131580 (C=N).7.99 (d, 2H, 2CH), 8.87 (d, 2H, 2CH).122.1 (2C5), 126.3 (2C4), 152.6 (2C–Cl), 178 (2C–S).