Ethanolic solution (40 ml) of compound 9 (1.2 g, 0.0035 mole), the appropriate benzaldehyde
derivatives 10-14 and catalytic amount of glacial acetic acid (1 ml) was refluxed for 2-4 hrs. After
the reaction completion, the solvent was removed under vacuum, and the solid formed was collected
and crystallized from aqueous ethanol to obtained compounds 15-19. 15: Yield%: 46.3, mp: 274-
7oC, C25H21N5OS, 1H-NMR (400 MHz, DMSo-d6); δ 2.37 (s, 3H, CH3), 2.64 (s, 3H, CH3), 3.12 (s,
3H, CH3), 7.18 (d, 1H, J = 8.0 Hz, Ar-H), 7.29 (d, 1H, J = 7.5 Hz, Ar-H), 7.33 (s, 1H, N=CH), 7.40
(t, 2H, J = 15.0 Hz, Ar-H), 7.65 (d, 1H, J = 8.0 Hz, Ar-H), 7.72 (d, 1H, J = 8.0 Hz, Ar-H), 7.80 (d,
1H, J = 7.5 Hz, Ar-H), 7.91 (d, 1H, J = 8.0 Hz, Ar-H), 8.03 (d, 1H, J = 8.0 Hz, Ar-H), 8.10 (d, 1H, J
13
= 8.5 Hz, Ar-H), 8.29 (s, 1H, NH). C-NMR δ 14.3, 21.5, 23.2, 112.6, 118.5, 121.4, 122.1, 124.1,
127.2, 129.3, 130.0, 130.8, 131.6, 137.4, 140.3, 140.7, 145.3, 148.2, 150.3, 151.0, 154.8, 155.3,
156.7, 163.9, 169.8. MS m/z (%): 439 (17.6, M+). 16: Yield%: 51.2, mp: 252-5oC, C24H18ClN5OS,
1H-NMR (500 MHz, DMSo-d6); δ 2.63 (s, 3H, CH3), 3.11 (s, 3H, CH3), 7.28 (t, 1H, J = 15.5 Hz,
Ar-H), 7.37 (t, 1H, J = 16.0 Hz, Ar-H), 7.43 (d, 1H, J = 6.5 Hz, Ar-H), 7.53 (d, 1H, J = 8.0 Hz, Ar-
H), 7.70 (d, 1H, J = 8.0 Hz, Ar-H), 7.77 (d, 2H, J = 8.5 Hz, Ar-H), 7.80 (s, 1H, N=CH), 7.89 (d, 1H,
J = 8.5 Hz, Ar-H), 8.02 (d, 1H, J = 8.0 Hz, Ar-H), 8.09 (d, 1H, J = 8.0 Hz, Ar-H), 8.31 (s, 1H, NH).
13C-NMR δ 13.9, 22.8, 56.0, 110.7, 112.1, 118.4, 118.5, 128.8, 129.0, 137.0, 146.7, 147.8, 150.5,
156.3, 160.7, 163.6, 169.5. MS m/z (%): 459 (11.4, M+). 17: Yield%: 39.7, mp: 226-8oC,
C25H21N5O2S, 1H-NMR (400 MHz, DMSo-d6); δ 2.94 (s, 3H, CH3), 3.12 (s, 3H, CH3), 3.82 (s, 3H,
OCH3), 6.92 (d, 1H, J = 8.5 Hz, Ar-H), 7.04 (d, 2H, J = 9.0 Hz, Ar-H), 7.29 (t, 1H, J = 15.5 Hz, Ar-
H), 7.38 (t, 1H, J = 14.5 Hz, Ar-H), 7.71 (d, 1H, J = 12.5 Hz, Ar-H), 7.77 (d, 1H, J = 13.5 Hz, Ar-H),
7.90 (d, 1H, J = 8.0 Hz, Ar-H), 8.01 (d, 1H, J = 8.0 Hz, Ar-H), 8.07 (d, 1H, J = 12.5 Hz, Ar-H), 8.27
13
(s, 1H, N=CH), 11.86 (s, 1H, NH). C-NMR δ 13.9, 22.8, 55.3, 112.2, 114.4, 118.4, 118.6, 121.0,
121.4, 124.0, 128.3, 128.9, 129.0, 130.0, 130.4, 136.9, 147.8, 148.0, 154.3, 156.3, 161.0, 163.3,
1
169.2. MS m/z (%):455 (25.7, M+). 18: Yield%: 56.7, mp: 241-5oC, C26H23N5O3S, H-NMR (400
MHz, DMSo-d6); δ 2.64 (s, 3H, CH3), 3.11 (s, 3H, CH3), 3.74 (s, 3H, OCH3), 3.82 (s, 3H, OCH3),
6.98 (s, 1H, Ar-H), 7.04 (d, 1H, J = 8.5 Hz, Ar-H), 7.22 (d, 1H, J = 8.0 Hz, Ar-H), 7.29 (t, 1H, J =
15.0 Hz, Ar-H), 7.38 (t, 1H, J = 15.0 Hz, Ar-H), 7.70 (d, 1H, J = 8.5 Hz, Ar-H), 7.78 (d, 1H, J = 7.5
Hz, Ar-H), 8.00 (d, 1H, J = 8.0 Hz, Ar-H), 8.07 (d, 1H, J = 8.0 Hz, Ar-H), 8.24 (s, 1H, N=CH),
11.88 (s, 1H, NH). 13C-NMR δ 13.8, 22.8, 55.5, 55.6, 108.2, 108.6, 111.4, 111.6, 112.2, 118.4,
118.6, 121.0, 122.1, 136.9, 143.9, 147.8, 148.2, 149.1, 163.3, 169.3. MS m/z (%): 485 (17.4, M+).
1
19: Yield%: 57, mp: 250-5oC,C24H18N6O3S, H-NMR (400 MHz, DMSo-d6); δ 2.83 (s, 3H, CH3),
2.91 (s, 3H, CH3), 7.30 (t, 1H, J = 15.0 Hz, Ar-H), 7.75(d, 1H, J = 8.5 Hz, Ar-H), 7.85 (t, 1H, J = 15
Hz, Ar-H), 8.02(d, 2H, J = 8.0 Hz, Ar-H), 8.13 (d, 1H, J = 8.0 Hz, Ar-H), 8.18 (d, 1H, J = 8.0 Hz,
17