| Comp. | IR cm−1 |
1H NMR ppm |
13C-NMR ppm |
| 2a | 3380 (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). |
| 2b | 3410 (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). |
| 2c | 3385 (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). |
| 3 | 3370 (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). |
| 4 | 3420 (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). |
| 5 | 3310 (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). |
| 6 | 3427-3409 (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). |
| 7a | 3357 (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). |
| 7b | 3349 (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) |
| 8a | 3420 (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). |
| 8b | 3406 (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). |
| 9 | 3360 (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). |
| 10 | 1605 (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). |
| 11 | 1620 (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). |
| 12 | 3340 (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). |
| 13 | 1580 (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). |
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