SYNTHESIS AND ANTIMICROBIAL ACTIVITY
717
1590 (2C N), 1522, 1339 (NO2), 689 (C-S-C); 1H NMR (DMSO-d6, δ ppm): 4.71 (s, 2H,
CH2-N), 7.53–8.63 (m, 11H, Ar-H); 13C NMR (DMSO-d6, δ ppm): 50.2, 117.7, 118.9,
119.9, 121.2, 122.3, 123.7, 127.1, 127.6, 128.1, 131.2, 132.8, 140.1, 140.5, 146.0, 146.8,
155.1, 156.5, 160.5, 164.8, 176.9, 180.4. MS m/z (rel. Int.%): calcd. for C24H13N7O5S3:
575.60; found: 575.88 (M+). Anal. calcd. for C24H13N7O5S3: C, 50.08; H, 2.28; N, 17.03;
S, 16.71; found: C, 50.15; H, 2.19; N, 17.10; S, 16.65.
2-(4-Chlorophenyl)-3-((3-(6-Nitrobenzo[d]Thiazol-2-yl)-4-oxo-3,4-Dihy-
droquinazolin-2-yl)Methyl)-1,3,4-Thiadiazol-3-ium-5-Thiolate (6f). Yield: 68%;
mp 212◦C–214◦C; IR spectrum (KBr, ν, cm−1): 2922, 2863 (CH2), 1682 (CO), 1643,
1591 (2C N), 1525, 1341 (NO2), 772 (C-Cl), 687 (C-S-C); 1H NMR (DMSO-d6, δ ppm):
4.70 (s, 2H, CH2-N), 7.62–8.65 (m, 11H, Ar-H); 13C NMR (DMSO-d6, δ ppm): 49.9,
117.8, 119.0, 120.4, 121.6, 122.3, 127.6, 127.8, 127.9, 129.2, 131.4, 132.7, 133.3, 135.2,
140.1, 146.8, 155.2, 156.6, 160.1, 164.9, 176.6, 180.3. MS m/z (rel. Int.%): calcd. for
C24H13ClN6O3S3: 565.05; found: 565.23 (M+). Anal. calcd. for C24H13ClN6O3S3: C,
51.01; H, 2.32; N, 14.87; S, 17.02; found: C, 50.92; H, 2.38; N, 14.93; S, 16.98.
2-(2-Chlorophenyl)-3-((3-(6-Nitrobenzo[d]Thiazol-2-yl)-4-oxo-3,4-Dihy-
droquinazolin-2-yl)Methyl)-1,3,4-Thiadiazol-3-ium-5-Thiolate (6g). Yield: 74%;
mp 241◦C–243◦C; IR spectrum (KBr, ν, cm−1): 2928, 2860 (CH2), 1679 (CO), 1645, 1592
(2C N), 1527, 1343 (NO2), 685 (C-S-C), 776 (C-Cl); 1H NMR (DMSO-d6, δ ppm): 4.71
(s, 2H, CH2-N), 7.41–8.62 (m, 11H, Ar-H); 13C NMR (DMSO-d6, δ ppm): 50.0, 117.9,
119.1, 120.0, 121.5, 122.2, 125.5, 127.2, 127.7, 128.1, 130.1, 131.2, 131.8, 132.0, 132.6,
133.3, 139.8, 146.8, 155.3, 156.8, 160.1, 164.8, 176.5, 180.3. MS m/z (rel. Int.%): calcd.
for C24H13ClN6O3S3: 565.05; found: 565.19 (M+). Anal. calcd. for C24H13ClN6O3S3: C,
51.01; H, 2.32; N, 14.87; S, 17.02; found: C, 51.09; H, 2.38; N, 14.81; S, 17.07.
3-((3-(6-Nitrobenzo[d]Thiazol-2-yl)-4-oxo-3,4-Dihydroquinazolin-2-yl)
Methyl)-2-(2-Nitrophenyl)-1,3,4-Thiadiazol-3-ium-5-Thiolate (6h). Yield: 62%;
mp 215◦C–217◦C; IR spectrum (KBr, ν, cm−1): 2931, 2865 (CH2), 1680 (CO), 1637,
1591 (2C N), 1522, 1349 (NO2), 686 (C-S-C); 1H NMR (DMSO-d6, δ ppm): 4.72 (s, 2H,
CH2-N), 7.65–8.59 (m, 11H, Ar-H); 13C NMR (DMSO-d6, δ ppm): 50.2, 117.8, 119.3,
120.1, 121.6, 122.2, 123.7, 125.5, 127.4, 128.2, 130.7, 131.3, 132.7, 133.3, 134.4, 140.4,
146.8, 149.4, 155.2, 156.7, 160.1, 164.8, 176.4, 180.5. MS m/z (rel. Int.%): calcd. for
C24H13N7O5S3: 575.60; found: 575.82 (M+). Anal. calcd. for C24H13N7O5S3: C, 50.08;
H, 2.28; N, 17.03; S, 16.71; found: C, 50.01; H, 2.35; N, 17.11; S, 16.78.
2-(3,4-Dichlorophenyl)-3-((3-(6-Nitrobenzo[d]Thiazol-2-yl)-4-oxo-3,4-Di-
hydroquinazolin-2-yl)Methyl)-1,3,4-Thiadiazol-3-ium-5-Thiolate
(6i). Yield:
70%; mp 265◦C–267◦C; IR spectrum (KBr, ν, cm−1): 2939, 2862 (CH2), 1687 (CO),
1
1641, 1599 (2C N), 1519, 1346 (NO2), 771 (C-Cl), 689 (C-S-C); H NMR (DMSO-d6,
δ ppm): 4.70 (s, 2H, CH2-N), 7.47–8.63 (m, 10H, Ar-H); 13C NMR (DMSO-d6, δ ppm):
50.1, 117.7, 119.1, 119.9, 121.7, 122.4, 127.7, 126.6, 128.1, 130.9, 131.0, 131.2, 131,5,
132.7, 133.4, 134.6, 140.2, 146.9, 155.3, 156.7, 160.3, 165.1, 176.2, 180.4. MS m/z
(rel. Int.%): calcd. for C24H12Cl2N6O3S3: 599.49; found: 599.29 (M+). Anal. calcd. for
C24H12Cl2N6O3S3: C, 48.08; H, 2.02; N, 14.02; S, 16.05, found: C, 48.18; H, 1.96; N,
14.10; S,16.11.
2-(2-Chloro-5-Nitrophenyl)-3-((3-(6-Nitrobenzo[d]Thiazol-2-yl)-4-oxo-
3,4-Dihydroquinazolin-2-yl)Methyl)-1,3,4-Thiadiazol-3-ium-5-Thiolate
(6j).
Yield: 73%; mp 194◦C–196◦C; IR spectrum (KBr, ν, cm−1): 2935, 2861 (CH2), 1686
(CO), 1649, 1595 (2C N), 1527, 1344 (NO2), 772 (C-Cl), 683 (C-S-C); 1H NMR (DMSO-
d6, δ ppm): 4.71 (s, 2H, CH2-N), 7.64–8.62 (m, 10H, Ar-H); 13C NMR (DMSO-d6, δ