Table 2.
Physical and spectroscopic data of compounds 17–31
| Compounds | Yield (%) | Mp (°C) | Formula | HRMS-EI, m/z (calcd.) | 1H NMR (DMSO-d6)δ |
|---|---|---|---|---|---|
| 17 (MJ70) | 70 | 174–175 | C19H14N2O2 | 302.1057 (302.1055) | 3.87 (3H, s, OCH3), 7.22–7.34 (2H, m, 2 × ArH), 7.53–7.72 (5H, m, 5 × ArH), 7.95–8.22 (3H, m, 3 × ArH), 12.62 (1H, br s, NH) |
| 18 (MJ74) | 68 | 311–312 | C17H13N3O2 | 291.1001 (291.1008) | 3.84 (3H, s, OCH3), 7.15–7.19 (2H, m, 2 × ArH), 7.35–7.49 (3H, m, 3 × ArH), 7.63–7.68 (1H, m, 1 × ArH), 8.45 (1H, s, 1 × ArH), 8.46–8.63 (1H, m, 1 × ArH), 11.76 (1H, s, NH), 12.11 (1H, br s, NH) |
| 19 (MJ79) | 60 | 289–290 | C17H12N2O2S | 308.0628 (308.0619) | 3.89 (3H, s, OCH3), 7.43–7.57 (4H, m, 4 × ArH), 7.76–7.80 (1H, m, 1 × ArH), 8.07–8.11 (1H, m, 1 × ArH), 8.73 (1H, s, 1 × ArH), 8.98–9.01 (1H, m, 1 × ArH), 12.49 (1H, br s, NH) |
| 20 (MJ69) | 65 | 254–255 | C20H17N3O | 315.1367 (315.1372) | 2.99 [6H, s, N(CH3)2], 7.22–7.34 (2H, m, 2 × ArH), 7.51–7.72 (5H, m, 5 × ArH), 7.96–8.23 (3H, m, 3 × ArH), 12.39 (1H, br s, NH) |
| 21 (MJ75) | 60 | >300 | C18H16N4O | 304.1316 (304.1324) | 2.99 [6H, s, N(CH3)2], 7.17–7.34 (4H, m, 4 × ArH), 7.43–7.47 (1H, m, 1 × ArH), 7.58–7.63 (1H, m, 1 × ArH), 8.44 (1H, s, 1 × ArH), 8.65–8.69 (1H, m, 1 × ArH), 11.71 (1H, s, NH), 11.92 (1H, br s, NH) |
| 22 (MJ80) | 62 | >300 | C18H15N3OS | 321.0941 (321.0936) | 2.99 [6H, s, N(CH3)2], 7.20–7.67 (5H, m, 5 × ArH), 8.02–8.05 (1H, m, 1 × ArH), 8.63 (1H, s, 1 × ArH), 8.97–9.01 (1H, m, 1 × ArH), 12.21 (1H, br s, NH) |
| 23 (MJ66) | 65 | 276–277 | C22H19N3O | 341.1523 (341.1528) | 1.99 (4H, m, CH2CH2NCH2CH2), 3.27 (4H, m, CH2NCH2), 7.10–7.21 (2H, m, 2 × ArH), 7.56–7.76 (5H, m, 5 × ArH), 8.01–8.21 (3H, m, 3 × ArH), 12.34 (1H, br s, NH) |
| 24 (MJ65) | 61 | 298 | C20H18N4O | 330.1488 (330.1481) | 1.94 (4H, m, CH2CH2NCH2CH2), 3.28 (4H, m, CH2NCH2), 6.97–7.20 (4H, m, 4 × ArH), 7.39–7.43 (1H, m, 1 × ArH), 7.53–7.58 (1H, m, 1 × ArH), 8.38 (1H, s, 1 × ArH), 8.61–8.65 (1H, m, 1 × ArH), 11.68 (1H, s, NH), 11.88 (1H, br s, NH) |
| 25 (MJ78) | 60 | >300 | C20H17N3OS | 347.1090 (347.1092) | 1.97 (4H, m, CH2CH2NCH2CH2), 3.47 (4H, m, CH2NCH2), 7.43–7.57 (4H, m, 4 × ArH), 7.76–7.80 (1H, m, 1 × ArH), 8.07–8.11 (1H, m, 1 × ArH), 8.73 (1H, s, 1 × ArH), 8.98–9.02 (1H, m, 1 × ArH), 12.51 (1H, br s, NH) |
| 26 (MJ68) | 65 | 233–235 | C23H21N3O | 355.1680 (355.1685) | 1.57–1.62 [6H, m, (CH2)2CH2NCH2CH2], 3.26–3.31 (4H, m, CH2NCH2), 7.48–7.65 (6H, m, 6 × ArH), 7.72–7.76 (1H, m, 1 × ArH), 8.00–8.13 (3H, m, 3 × ArH), 12.43 (1H, br s, NH) |
| 27 (MJ72) | 64 | >300 | C21H20N4O | 344.1638 (344.1637) | 1.59–1.62 [6H, m, (CH2)2CH2NCH2CH2], 3.20–3.24 (4H, m, CH2NCH2), 7.18–7.21 (2H, m, 2 × ArH), 7.41–7.48 (3H, m, 3 × ArH), 7.50–7.62 (1H, m, 1 × ArH), 8.46 (1H, s, 1 × ArH), 8.65–8.69 (1H, m, 1 × ArH), 11.73 (1H, s, NH), 11.96 (1H, br s, NH) |
| 28 (MJ73) | 60 | >300 | C21H19N3OS | 361.1240 (361.1249) | 1.57–1.59 [6H, m, (CH2)2CH2NCH2CH2], 3.22–3.25 (4H, m, CH2NCH2), 7.42–7.54 (4H, m, 4 × ArH), 7.63–7.67 (1H, m, 1 × ArH), 8.03–8.07 (1H, m, 1 × ArH), 8.66 (1H, s, 1 × ArH), 8.97–9.00 (1H, m, 1 × ArH), 12.30 (1H, br s, NH) |
| 29 (MJ67) | 64 | 291–293 | C22H19N3O2 | 357.1470 (357.1477) | 3.22 (4H, t, J = 4.7 Hz, CH2NCH2), 3.77 (4H, t, J = 4.7 Hz, CH2OCH2), 7.51–7.66 (6H, m, 6 × ArH), 7.73–7.76 (1H, m, 1 × ArH), 8.00–8.11 (3H, m, 3 × ArH), 12.48 (1H, br s, NH) |
| 30 (MJ76) | 65 | >300 | C20H18N4O2 | 346.1434 (346.1430) | 2.97 (4H, t, J = 4.7 Hz, CH2NCH2), 3.74 (4H, t, J = 4.7 Hz, CH2OCH2), 7.12–7.22 (2H, m, 2 × ArH), 7.41–7.63 (4H, m, 4 × ArH), 8.43 (1H, s, 1 × ArH), 8.60–8.64 (1H, m, 1 × ArH), 11.76 (1H, s, NH), 12.01 (1H, br s, NH) |
| 31 (MJ77) | 60 | >300 | C20H17N3O2S | 363.1034 (363.1041) | 2.47 (4H, t, J = 4.7 Hz, CH2NCH2), 3.75 (4H, t, J = 4.7 Hz, CH2OCH2), 7.44–7.59 (4H, m, 4 × ArH), 7.67–7.72 (1H, m, 1 × ArH), 8.03–8.07 (1H, m, 1 × ArH), 8.67 (1H, s, 1 × ArH), 8.96–9.00 (1H, m, 1 × ArH), 12.31 (1H, br s, NH) |
HRMS-EI, high-resolution electron impact mass spectra; Mp, melting point.