Compound

Spectral Data

2

IR, v (cm−1): 3294,3208, 3173 (N-H), 2909 (CH3), 1659 (C=O), 1519 (C=N), 1215 (C=S); 1H NMR (CDCl3, 400 M Hz, δ ppm): δH = 10.3 (1H, s, -NH), 6.2 (2H, s, -NH2), 2.3 (3H, s, -CH3-C); 13C NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 168.4 (C=S), 148.8 (C=O), 145.2 (C=N), 16.5 (CH3); Anal.calcd. for C4H6N4OS: C 30.37, H 3.82, N 35.42; Found (%) C 30.46, H 3.77,N 35.43; MS/EI, m/z (I, %) for C4H6N4OS (m.w.: 158.19 g/mol): [M]+• 158(100), [M+• - CO]+ 130(4), [M+• - NCCH3]+ 89(1).

3

IR,v (cm−1): 3240 (N-H), 2965, 2924 (CH3), 1684 (C=O), 1483 (C=N),1255 (C=S); 1H NMR (CDCl3, 400 M Hz, δ ppm): δH = 10.5 (1H, s, -NH), 3.9 (3H, s, -CH3-N), 2.3 (3H, s, -CH3-C); 13C NMR (CDCl3, 100 M Hz, δ ppm): δC = 172.4 (C=S), 152.8 (C=O), 148.7 (C=N), 44.9 (CH3-N)16.2 (CH3); Anal.calcd. for C5H7N3OS: C 38.20, H 4.49, N 26.73; Found (%) C 38.23, H 4.40N 26.83; MS/EI, m/z (I, %) for C5H7N3OS (m.w.: 157.19 g/mol): [M]+• 157(100), [M+• - CO]+ 129(4), [M+• - NCCH3]+ 88(6), [M+• - CH3]+ 73(14).

4

IR, v (cm−1): 3304 (O-H), 3244 (N-H), 3072 - 2939 (CH3), 1755 (C=O), 1605 (C=N), 1067 (C=S); 1H NMR (DMSO-d6, 400 M Hz, δ ppm): δH = 13.5 (1H, s, -OH), 12.5 (1H, s, -NH), 7.4 - 7.3 (5H, m, aromatic C-H), 4.4 (2H, s, S-CH2-), 2.1 (3H, s, CH3-C=N-); 13C NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 201.4 (C=S), 165.9 (-COOH), 144.5 (C=N), 136.9 - 127.7 (aromatic ring carbon), 38.5 (S-CH2-), 20.7 (CH3-C=N-); Anal.calcd. for C11H12N2O2S2: C 49.23, H 4.51, N 10.44; Found (%) C 49.21, H 4.33, N 10.54; MS/EI, m/z (I, %) for C11H12N2O2S2 (m.w.: 268.36 g/mol): [M]+• 268(1), [M+• - COOH]+ 223(14), [M+• - CH3C=NNHCS]+ 124(15), [M+• - S]+ 91(100).

5

IR, v (cm−1): 3323 (O-H), 3248 (N-H), 2947 - 2853 (CH3), 1755 (C=O), 1612 (C=N), 1069 (C=S); 1H NMR (DMSO-d6, 400 M Hz, δ ppm): δH = 13.5 (1H, s, -OH), 12.4 (1H, s, -NH), 3.2 (2H, s, S-CH2-), 2.0 (3H, s, CH3-C=N-), 1.3 - 1.5 (12H, m, -CH2-), 0.8 (3H, t, -CH3); 13C NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 202.3 (C=S), 166.1 (-COOH), 144.3 (C=N), 31.6 (S-CH2-), 28.9-28.3 (-CH2-), 22.5 (CH3-C=N-), 14.4 (-CH3); Anal.calcd. forC12H22N2O2S2: C 49.62, H 7.63, N 9.64; Found (%) C 49.54, H 7.47, N 9.86; MS/EI, m/z (I, %) for C12H22N2O2S2 (m.w.: 290.45 g/mol): [M]+• 290(1), [M+• - COOH]+ 245(23), [M+• - S-C8H17]+ 146(15).