Med Chem Res
2-(1-(4-(4-(4-Hydroxybenzylidene)-2-methyl-5-oxo-4,5-
dihydro-1H-imidazol-1-yl)phenyl)ethylidene)
hydrazinecarbothioamide (3j)
2-(1-(4-(2-Methyl-4-(4-methylbenzylidene)-5-oxo-4,5-
dihydro-1H-imidazol-1-yl)phenyl)ethylidene)
hydrazinecarbothioamide (3m)
Yield: 61 %; m.p.: 166–168 °C; IR (KBr) mmax/cm-1
:
Yield: 63 %; m.p.: 205–207 °C; IR (KBr) mmax/cm-1
3,410, 3,345 (NH2), 3,239 (NH), 3,060 (C–H, aromatic),
:
3,421 (OH), 3,413, 3,356 (NH2), 3,263 (NH), 3,083 (C–H,
aromatic), 2,929, 3,013 (C–H), 1,684 (C=O), 1,580 (C=N),
1,517 (C=C), 1,333 (C=S); 1H NMR (300 MHz, DMSO-d6,
d, ppm): 2.06 (s, 3H, CH3), 2.34 (s, 3H, CH3), 7.07 (s, 1H,
NH), 7.36 (s, 1H, CH=C), 6.64–7.88 (m, 8H, Ar–H), 8.54
(s, 2H, NH2), 9.15 (s, 1H, OH); 13C NMR (100 MHz,
DMSO-d6, d, ppm): 16.7, 21.3, 114.6, 116.1, 124.6, 127.6,
129.3, 130.6, 130.9, 133.2, 135.6, 147.4, 157.8, 166.3,
170.8, 181.3; LCMS (m/z): 393 (M?); Anal. Calcd. For
C20H19N5O2S: C-61.05, H-4.87, N-17.80; Found: C-61.09,
H-4.81, N-17.84 %.
2,931, 3,009 (C–H), 1,687 (C=O), 1,579 (C=N), 1,525
1
(C=C), 1,335 (C=S); H NMR (300 MHz, DMSO-d6, d,
ppm): 2.02 (s, 3H, CH3), 2.34 (s, 3H, CH3), 2.40 (s, 3H,
CH3), 7.02 (s, 1H, NH), 7.14–7.89 (m, 8H, Ar–H), 7.81 (s,
1H, CH=C), 8.52 (s, 2H, NH2); 13C NMR (100 MHz,
DMSO-d6, d, ppm): 16.4, 21.1, 21.7, 114.2, 124.4, 128.5,
128.9, 129.6, 130.7, 132.3, 133.7, 137.6, 135.4, 147.3,
166.5, 170.4, 181.6; LCMS (m/z): 391 (M?); Anal. Calcd.
For C21H21N5OS: C-64.43, H-5.41, N-17.89; Found:
C-64.48, H-5.48, N-17.93 %.
2-(1-(4-(2-Methyl-4-(2-methylbenzylidene)-5-oxo-4,5-
dihydro-1H-imidazol-1-yl)phenyl)ethylidene)
hydrazinecarbothioamide (3k)
2-(1-(4-(4-(2-Methoxybenzylidene)-2-methyl-5-oxo-4,5-
dihydro-1H-imidazol-1-yl)phenyl)ethylidene)
hydrazinecarbothioamide (3n)
Yield: 64 %; m.p.: 188–190 °C; IR (KBr) mmax/cm-1
:
Yield: 64 %; m.p.: 188–190 °C; IR (KBr) mmax/cm-1
:
3,418, 3,354 (NH2), 3,261 (NH), 3,075 (C–H, aromatic),
2,924, 3,003 (C–H), 1,688 (C=O), 1,575 (C=N), 1,512
3,417, 3,349 (NH2), 3,238 (NH), 3,058 (C–H, aromatic),
2,927, 3,009 (C–H), 1,683 (C=O), 1,581 (C=N), 1,522
1
1
(C=C), 1,337 (C=S); H NMR (300 MHz, DMSO-d6, d,
(C=C), 1,329 (C=S); H NMR (300 MHz, DMSO-d6, d,
ppm): 2.03 (s, 3H, CH3), 2.34 (s, 3H, CH3), 2.50 (s, 3H,
CH3), 7.02 (s, 1H, NH), 6.19–7.88 (m, 8H, Ar–H), 8.05 (s,
1H, CH=C), 8.54 (s, 2H, NH2); 13C NMR (100 MHz,
DMSO-d6, d, ppm): 16.6, 19.4, 21.4, 108.4, 124.7, 125.4,
126.6, 127.4, 127.9, 129.5, 130.6, 133.5, 135.7, 136.1,
136.4, 147.5, 166.7, 170.8, 181.3; LCMS (m/z): 391 (M?);
Anal. Calcd. For C21H21N5OS: C-64.43, H-5.41, N-17.89;
Found: C-64.51, H-5.34, N-17.82 %.
ppm): 2.07 (s, 3H, CH3), 2.34 (s, 3H, CH3), 3.57 (s, 3H,
CH3), 7.03 (s, 1H, NH), 6.94–7.88 (m, 8H, Ar–H), 7.62 (s,
1H, CH=C), 8.56 (s, 2H, NH2); 13C NMR (100 MHz,
DMSO-d6, d, ppm): 16.4, 21.7, 56.3, 108.5, 114.6, 120.7,
124.4, 128.3, 128.5, 129.6, 130.7, 133.7, 135.4, 147.3,
159.4, 166.5, 170.4, 181.6; LCMS (m/z): 407 (M?); Anal.
Calcd. For C21H21N5O2S: C-61.90, H-5.19, N-17.19;
Found: C-61.84, H-5.25, N-17.14 %.
2-(1-(4-(2-Methyl-4-(3-methylbenzylidene)-5-oxo-4,5-
dihydro-1H-imidazol-1-yl)phenyl)ethylidene)
hydrazinecarbothioamide (3l)
2-(1-(4-(4-(4-Methoxybenzylidene)-2-methyl-5-oxo-4,5-
dihydro-1H-imidazol-1-yl)phenyl)ethylidene)
hydrazinecarbothioamide (3o)
Yield: 60 %; m.p.: 216–218 °C; IR (KBr) mmax/cm-1
:
Yield: 61 %; m.p.: 167–169 °C; IR (KBr) mmax/cm-1
:
3,412, 3,338 (NH2), 3,248 (NH), 3,066 (C–H, aromatic),
2,937, 3,011 (C–H), 1,681 (C=O), 1,572 (C=N), 1,518
3,414, 3,342 (NH2), 3,239 (NH), 3,061 (C–H, aromatic),
2,925, 3,005 (C–H), 1,689 (C=O), 1,586 (C=N), 1,525
1
1
(C=C), 1,330 (C=S); H NMR (300 MHz, DMSO-d6, d,
(C=C), 1,332 (C=S); H NMR (300 MHz, DMSO-d6, d,
ppm): 2.04 (s, 3H, CH3), 2.31 (s, 3H, CH3), 2.43 (s, 3H,
CH3), 7.00 (s, 1H, NH), 7.06–7.87 (m, 8H, Ar–H), 7.38 (s,
1H, CH=C), 8.54 (s, 2H, NH2); 13C NMR (100 MHz,
DMSO-d6, d, ppm): 16.3, 21.5, 21.8, 114.5, 124.6, 125.7,
126.8, 128.1, 128.6, 129.2, 130.6, 133.5, 135.4, 135.7,
138.4, 147.3, 166.6, 170.7, 181.3; LCMS (m/z): 391 (M?);
Anal. Calcd. For C21H21N5OS: C-64.43, H-5.41, N-17.89;
Found: C-64.38, H-5.47, N-17.94 %.
ppm): 2.02 (s, 3H, CH3), 2.33 (s, 3H, CH3), 3.55 (s, 3H,
CH3), 7.02 (s, 1H, NH), 6.92–7.88 (m, 8H, Ar–H), 7.36 (s,
1H, CH=C), 8.53 (s, 2H, NH2); 13C NMR (100 MHz,
DMSO-d6, d, ppm): 16.2, 21.5, 55.4, 114.3, 114.6, 124.6,
127.6, 129.3, 130.4, 130.7, 133.1, 135.6, 147.7, 159.8,
166.2, 170.6, 181.3; LCMS (m/z): 407 (M?); Anal. Calcd.
For C21H21N5O2S: C-61.90, H-5.19, N-17.19; Found:
C-61.95, H-5.13, N-17.26 %.
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