2168
Med Chem Res (2013) 22:2163–2173
1
phenyl isothiocyanate was poured into the solution of
hydrazide with continuous stirring. The reaction mixture
was refluxed for 8 h. The white solid obtained on cooling
the reaction mixture to room temperature was filtered,
dried, and recrystallized from dichloromethane.
IR (KBr, cm-1): 1246 (C=S), 1682 (C=O); H-NMR
(DMSO-d6, d ppm): 11.15 (d, 1H, NH), 10.45 (d, 1H, NH),
10.72 (s, 1H, NH), 7.19–7.76 (m, 14H, Ar–H), 4.10 (s, 2H,
SCH2), 3.73 (s, 3H, OCH3); 13C-NMR (DMSO-d6, d ppm):
169.57 (–CONH), 181.32 (C=S), 152.87 (C3 of triazole),
147.67 (C5 of triazole), 137.92 (C1 of phenyl ring), 130.75
(C2 and C6 of phenyl ring), 128.78 (C3 and C5 of phenyl
ring), 127.17 (C4 of phenyl ring), 40.78 (–SCH2), 55.93
(CH3); MS m/z: 490 [M?] (58).
1
IR (KBr, cm-1): 1243 (C=S), 1703 (C=O); H-NMR
(DMSO-d6, d ppm): 11.20 (d, 1H, NH), 10.80 (d, 1H, NH),
10.21(s, 1H, NH), 7.02–7.55 (m, 15H, Ar–H), 4.12 (s, 2H,
SCH2); 13C-NMR (DMSO-d6, d ppm): 170.34 (–CONH),
181.53 (C=S), 153.18 (C3 of triazole), 147.64 (C5 of tria-
zole), 137.14 (C1 of phenyl ring), 130.73 (C2 and C6 of
phenyl ring), 129.34 (C3 and C5 of phenyl ring), 128.67 (C4
of phenyl ring), 41.52 (-SCH2); MS m/z: 460 [M?] (55).
Synthesis of 1-[2-(4,5-diphenyl-4H-1,2,4-triazole-3-
ylthio)acetyl]-4-(4-ethoxyphenyl) thiosemicarbazide (3e)
The experimental procedure was repeated with 2a (0.01
mol, 3.25 g) and 4-ethoxyphenyl isothiocyanate (0.01 mol,
1.79 g) in 25 ml absolute ethanol.
Synthesis of 1-[2-(4,5-diphenyl-4H-1,2,4-triazole-3-
ylthio)acetyl]-4-(4-flurophenyl) thiosemic arbazide (3b)
1
IR (KBr, cm-1): 1253 (C=S), 1690 (C=O); H-NMR
The experimental procedure was repeated with 2a (0.01
mol, 3.25 g) and 4-fluorophenyl isothiocyanate (0.01 mol,
1.53 g) in 25 ml absolute ethanol.
(DMSO-d6, d ppm): 11.43 (d, 1H, NH), 10.78 (d, 1H, NH),
10.67 (s, 1H, NH), 7.25–7.76 (m, 14H, Ar–H), 4.24 (s, 2H,
SCH2), 3.98 (q, 2H, CH2), 1.33 (t, 3H, CH3); 13C-NMR
(DMSO-d6, d ppm): 170.27 (–CONH), 180.54 (C=S),
152.12 (C3 of triazole), 148.74 (C5 of triazole), 137.14 (C1
of phenyl ring), 129.29 (C2 and C6 of phenyl ring), 128.61
(C3 and C5 of phenyl ring), 127.56 (C4 of phenyl ring),
41.36 (–SCH2), 64.72 (OCH2), 14.8 (CH3); MS m/z: 504
[M?] (75).
1
IR (KBr, cm-1): 1256 (C=S), 1675 (C=O); H-NMR
(DMSO-d6, d ppm): 11.12 (d, 1H, NH), 10.65 (d, 1H, NH),
10.13 (s, 1H, NH), 7.10-7.63 (m, 14H, Ar–H), 4.21 (s, 2H,
SCH2); 13C-NMR (DMSO-d6, d ppm): 170.68 (–CONH),
180.63 (C=S), 153.91 (C3 of triazole), 148.23 (C5 of tria-
zole), 137.23 (C1 of phenyl ring), 130.78 (C2 and C6 of
phenyl ring), 128.69 (C3 and C5 of phenyl ring), 128.52 (C4
of phenyl ring), 41.62 (–SCH2); MS m/z: 478 [M?] (65).
Synthesis of 1-[2-(4,5-diphenyl-4H-1,2,4-triazole-3-
ylthio)acetyl]-4-(isopropyl) thiosemicarbazide (3f)
Synthesis of 1-[2-(4,5-diphenyl-4H-1,2,4-triazole-3-
ylthio)acetyl]-4-(4-chlorophenyl) thiosemicarbazide (3c)
The experimental procedure was repeated with 2a (0.01 mol,
3.25 g) and isopropyl isothiocyanate (0.01 mol, 1.01 g) in 25
ml absolute ethanol.
The experimental procedure was repeated with 2a (0.01
mol, 3.25 g) and 4-chlorophenyl isothiocyanate (0.01 mol,
1.69 g) in 25 ml absolute ethanol.
1
IR (KBr, cm-1): 1250 (C=S), 1685 (C=O); H-NMR
(DMSO-d6, d ppm): 11.37 (d, 1H, NH), 10.21 (d, 1H, NH),
10.65 (s, 1H, NH), 7.12-7.63 (m, 10H, Ar–H), 4.18 (s, 2H,
SCH2), 3.97 (m, 1H, CH), 1.36 (d, 6H, 2CH3); 13C-NMR
(DMSO-d6, d ppm): 169.94 (–CONH), 181.23 (C=S),
151.34 (C3 of triazole), 148.67 (C5 of triazole), 137.84 (C1
of phenyl ring), 129.78 (C2 and C6 of phenyl ring), 127.45
(C3 and C5 of phenyl ring), 126.32 (C4 of phenyl ring),
40.65 (–SCH2), 48.23 (CH), 23.54 (CH3); MS m/z: 426
[M?] (65).
1
IR (KBr, cm-1): 1248 (C=S), 1692 (C=O); H-NMR
(DMSO-d6, d ppm): 11.63 (d, 1H, NH), 10.73 (d, 1H, NH),
10.76 (s, 1H, NH), 7.22–7.86 (m, 14H, Ar–H), 4.14 (s, 2H,
SCH2); 13C-NMR (DMSO-d6, d ppm): 170.67 (–CONH),
180.29 (C=S), 152.45 (C3 of triazole), 148.97 (C5 of tria-
zole), 137.38 (C1 of phenyl ring), 131.25 (C2 and C6 of
phenyl ring), 128.17 (C3 and C5 of phenyl ring), 127.64 (C4
of phenyl ring), 40.18 (–SCH2); MS m/z: 494 [M?] (62).
Synthesis of 1-[1-(4,5-diphenyl-4H-1,2,4-triazole-3-
ylthio)formyl]-4-phenyl thiosemicarbazide (3g)
Synthesis of 1-[2-(4,5-diphenyl-4H-1,2,4-triazole-
3-ylthio)acetyl]-4-(4-methoxyphenyl)
thiosemicarbazide (3d)
The experimental procedure was repeated with 2b (0.01
mol, 3.25 g) and phenyl isothiocyanate in 25 ml absolute
ethanol.
The experimental procedure was repeated with 2a (0.01
mol, 3.25 g) and 4-methoxyphenyl isothiocyanate (0.01
mol, 1.65 g) in 25 ml absolute ethanol.
1
IR (KBr, cm-1): 1247 (C=S), 1688 (C=O); H-NMR
(DMSO-d6, d ppm): 11.02 (d, 1H, NH), 10.45 (d, 1H, NH),
123