Molecules 2013, 18
4149
(-C=C- pyrimidine ring), 1304 (C-O), 1168 (-NH-SO2), 1078 (CH aromatic ring), 965 (S-N), 839 (S-C);
1H-NMR δ: 8.56–8.89 (dm, 3H, pyrimidine ring), 8.24 (s, 1H, CO-NH), 8.07 (s, 1H, N=CH), 7.35–7.89
(d, 8H, Ar-H), 5.05 (s, 1H, Ar-OH), 4.17 (s, 1H, -NH-SO2), 3.63 (d, 2H, CH2), 3.44 (m, 1H, HN-N).
N4-(4-Nitrobenzylidene)hydrazinoacetylamino-N1-(pyrimidin-2-yl)benzensulfonamide (4a6). Yield 75%,
m.p. 227–230 C; IR (KBr, cm−1): 3445 (-NH), 2851 (CH2-NH), 2932 (=CH- pyrimidine ring), 1689
(C=O), 1623 (HN-CO), 1592 (-C=C- aromatic ring), 1536 (N=CH), 1514 (-C=C- pyrimidine ring), 1343
1
(C-NO2), 1316 (C-O), 1174 (-NH-SO2), 1078 (CH aromatic ring), 951 (S-N), 837 (S-C); H-NMR δ:
8.50–8.87 (dm, 3H, pyrimidine ring), 8.21 (s, 1H, CO-NH), 8.06 (s, 1H, N=CH), 7.33–7.90 (d, 8H, Ar-H),
4.16 (s, 1H, -NH-SO2), 3.70 (d, 2H, CH2), 3.41 (m, 1H, HN-N).
N4-(Benzylidene)hydrazinoacetylamino-N1-(3,4-dimethyl-1,2-oxazol-5-yl)benzensulfonamide (4b1). Yield
87%, m.p. 118–120 C; IR (KBr, cm−1): 3465 (-NH), 2864 (CH2-NH), 1686 (C=O), 1625 (HN-CO),
1592 (-C=C- aromatic ring), 1518 (N=CH), 1496 (-C=C- oxazole ring), 1310 (C-O), 1151 (-NH-SO2),
1
1093 (CH aromatic ring), 956 (S-N), 830 (S-C); H-NMR δ: 8.41 (s, 1H, CO-NH), 8.12 (s, 1H,
N=CH), 7.21–7.93 (dm, 9H, Ar-H), 4.62 (s, 1H, -NH-SO2), 3.59 (d, 2H, CH2), 3.24 (m, 1H, HN-N),
2.01–2.38 (s, 6H, 2CH3).
N4-(4-Fluorobenzylidene)hydrazinoacetylamino-N1-(3,4-dimethyl-1,2-oxazol-5-yl)benzensulfonamide
(4b2). Yield 68%, m.p. 187–199 C; IR (KBr, cm−1): 3452 (-NH), 2863 (CH2-NH), 1697 (C=O), 1631
(HN-CO), 1601 (-C=C- aromatic ring), 1507 (N=CH), 1482 (-C=C- oxazole ring), 1320 (C-O), 1225
1
(C-F), 1153 (-NH-SO2), 1097 (CH aromatic ring), 962 (S-N), 824 (S-C); H-NMR δ: 8.36 (s, 1H,
CO-NH), 8.21 (s, 1H, N=CH), 7.18–7.91 (d, 8H, Ar-H), 4.65 (s, 1H, -NH-SO2), 3.62 (d, 2H, CH2),
3.38 (m, 1H, HN-N), 2.08–2.34 (s, 6H, 2CH3).
N4-(4-Chlorobenzylidene)hydrazinoacetylamino-N1-(3,4-dimethyl-1,2-oxazol-5-yl)benzensulfonamide (4b3).
Yield 62%, m.p. 175–178 C; IR (KBr, cm−1): 3451 (-NH), 2850 (CH2-NH), 1702 (C=O), 1622
(HN-CO), 1586 (-C=C- aromatic ring), 1540 (N=CH), 1483 (-C=C- oxazole ring), 1312 (C-O), 1169
1
(-NH-SO2), 1086 (CH aromatic ring), 957 (S-N), 830 (S-C), 814 (C-Cl); H-NMR δ: 8.31 (s, 1H,
CO-NH), 8.16 (s, 1H, N=CH), 7.25–7.98 (d, 8H, Ar-H), 4.74 (s, 1H, -NH-SO2), 3.64 (d, 2H, CH2),
3.39 (m, 1H, HN-N), 2.08–2.40 (s, 6H, 2CH3).
N4-(4-Bromobenzylidene)hydrazinoacetylamino-N1-(3,4-dimethyl-1,2-oxazol-5-yl)benzensulfonamide
(4b4). Yield 57%, m.p. 219 C; IR (KBr, cm−1): 3439 (-NH), 2870 (CH2-NH), 1669 (C=O), 1625
(HN-CO), 1591 (-C=C- aromatic ring), 1522 (N=CH), 1481 (-C=C- oxazole ring), 1315 (C-O), 1156
1
(-NH-SO2), 1095 (CH aromatic ring), 940 (S-N), 832 (S-C), 555 (C-Br); H-NMR δ: 8.32 (s, 1H,
CO-NH), 8.18 (s, 1H, N=CH), 7.36-7.94 (d, 8H, Ar-H), 4.61 (s, 1H, -NH-SO2), 3.65 (d, 2H, CH2), 3.39
(m, 1H, HN-N), 2.10–2.32 (s, 6H, 2CH3).
N4-(4-Hydroxybenzylidene)hydrazinoacetylamino-N1-(3,4-dimethyl-1,2-oxazol-5-yl)benzensulfonamide (4b5).
Yield 63%, m.p. 190–192 C; IR (KBr, cm−1): 3495 (C-OH), 3479 (-NH), 2859 (CH2-NH), 1659
(C=O), 1622 (HN-CO), 1593 (-C=C- aromatic ring), 1530 (N=CH), 1476 (-C=C- oxazole ring), 1323
1
(C-O), 1150 (-NH-SO2), 1094 (CH aromatic ring), 962 (S-N), 825 (S-C); H-NMR δ: 8.36 (s, 1H,