Study of Direction of Cyclization of 1-Azolil-4-Aryl/Alkyl-Thiosemicarbazides 529
Anal. Calcd for C13H13N5S: C, 57.54; H, 4.83; N,
25.81. Found: C, 57.41; H, 5.12; N, 25.67.
4-Ethyl-5-(pyrrol-2-yl)-s-triazole-3-thione
(30).
Yield 77%, mp 210–212◦C; IR (KBr, ν in cm−1):
3354 (NH), 2979, 1471, 1444, 1391 (Aliph.), 1663
1
4-(2-Fluorophenyl)-5-(4-methyl-imidazol-5-yl)-s-
triazole-3-thione (21). Yield 39%, mp 216–218◦C;
IR (KBr, ν in cm−1): 3387, 3268 (NH), 3058, 1596,
1572, 1505, 1480, 759 (ArH), 2921, 2882, 1462, 1383
(Aliph.), 1625 (C N), 1240 (C S); 1H NMR (300
MHz, DMSO-d6): δ 2.38 (s, 3H, CH3), 7.23–7.53
(m, 5H, 5×CH), 12.34, 13.95 (2s, 2H, 2×NH, D2O
exchangeable). Anal. Calcd for C12H10FN5S: C, 52.35;
H, 3.66; N, 25.44. Found: C, 52.06; H, 3.58; N, 25.33.
(C N), 1327 (C S); H NMR (300 MHz, DMSO-d6):
δ 1.22–1.26 (t, 3H, CH3), 4.16–4.23 (q, 2H, CH2),
6.24–6.26 (m, 1H, CH), 6.68–6.70 (m, 1H, CH),
6.99–7.02 (m, 1H, CH), 11.72, 13.78 (2s, 2H, 2×NH,
D2O exchangeable). Anal. Calcd for C8H10N4S: C,
49.46; H, 5.19; N, 28.84. Found: C, 49.45; H, 5.19; N,
28.84.
4-Phenyl-5-(4-methyl-1,2,3-thiadiazol-5-yl)-s-tria-
zole-3-thione (37). Yield 68%, mp 266–268◦C; IR
(KBr, ν in cm−1): 3263 (NH), 3091, 1588, 1493,
1485, 901, 754, 705 (ArH), 2971, 2876, 1463, 1392
(Aliph.), 1633 (C N), 1244 (C S); 1H NMR (300
MHz, DMSO-d6): δ 2.82 (s, 3H, CH3), 7.46–7.50 (m,
2H, 2×CH), 7.56–7.64 (m, 3H, 3×CH), 14.55 (s, 1H,
NH, D2O exchangeable). Anal. Calcd for C11H9N5S2:
C, 47.98; H, 3.92; N, 25.43. Found: C, 48.03; H, 3.21;
N, 25.24.
4-Cyclohexyl-5-(4-methyl-imidazol-5-yl)-s-triazo-
le-3-thione (22). Yield 36%, mp 234–236◦C; IR
(KBr, ν in cm−1): 3220 (NH), 2930, 1470, 1452, 1391,
730 (Aliph.), 1620 (C N), 1220 (C S); 1H NMR (300
MHz, DMSO-d6): δ 1.03–1.77 (m, 10H, 5×CH2), 2.26
(s, 3H, CH3), 4.85 (s, 1H, CH), 7.74 (s, 1H, CH),
12.43, 13.68 (2s, 2H, 2×NH, D2O exchangeable).
Anal. Calcd for C12H17N5S: C, 54.73; H, 6.51; N,
26.59. Found: C, 54.49; H, 6.56; N, 26.25.
4-(2-Methylphenyl)-5-(4-methyl-1,2,3-thiadiazol-
5-yl)-s-triazole-3-thione (38). Yield 55%, mp
263–265◦C; IR (KBr, ν in cm−1): 3225 (NH), 3050,
1586, 1490, 740 (ArH), 2933, 2871, 1395 (Aliph.),
4-(4-Methoxyphenyl)-5-(pyrrol-2-yl)-s-triazole-3-
thione (27). Yield 85%, mp 257–259◦C; IR (KBr, ν
in cm−1): 3426, 3318, 3233 (NH), 3083, 1588, 1516,
831 (ArH), 2835, 1451, 1416 (Aliph.), 1606 (C N),
1
1613 (C N), 1234 (C S); H NMR: δ 2.02 (s, 3H,
1
1334 (C S); H NMR (300 MHz, DMSO-d6): δ 3.85
CH3), 2.93 (s, 3H, CH3), 7.40–7.49 (m, 2H, 2×CH),
7.51–7.54 (m, 1H, CH), 7.59–7.64 (m, 1H, CH),
14.66 (s, 1H, NH, D2O exchangeable). Anal. Calcd
for C12H11N5S2: C, 49.81; H, 3.83; N, 24.20. Found:
C, 49.75; H, 4.54; N, 23.90.
(s, 3H, OCH3), 5.26–5.27 (m, 1H, CH), 5.92–5.94
(m, 1H, CH), 6.87–6.89 (m, 1H, CH), 7.10–7.13 (dd,
2H, 2×CH), 7.28–7.31 (dd, 2H, 2×CH), 11.73, 13.85
(2s, 2H, 2×NH, D2O exchangeable). Anal. Calcd for
C13H12N4OS: C, 57.34; H, 4.44; N, 20.57. Found: C,
57.37; H, 4.44; N, 20.23.
4-(2-Fluorophenyl)-5-(4-methyl-1,2,3-thiadiazol-
5-yl)-s-triazole-3-thione (39). Yield 50%, mp
261–263◦C; IR (KBr, ν in cm−1): 3256 (NH), 3087,
1616, 1600, 1515, 742 (ArH), 2876, 1451, 1366
4-(4-Bromophenyl)-5-(pyrrol-2-yl)-s-triazole-3-thi-
one (28). Yield 88%, mp 274–276◦C; IR (KBr, ν
in cm−1): 3462, 3315 (NH), 3089, 1519, 1490, 828
(ArH), 1607 (C N), 1328 (C S); 1H NMR (300 MHz,
DMSO-d6): δ 5.28–5.31 (m, 1H, CH), 5.95–5.98 (m,
1H, CH), 6.89–6.91 (m, 1H, CH), 7.37–7.42 (m, 2H,
2×CH), 7.78–7.83 (m, 2H, 2×CH), 11.77, 13.95 (2s,
2H, 2×NH, D2O exchangeable). Anal. Calcd for
C12H9BrN4S: C, 44.87; H, 2.82; N, 17.44. Found: C,
45.03; H, 2.51; N, 17.05.
1
(Aliph.), 1627 (C N), 1246 (C S); H NMR: δ 2.85
(s, 3H, CH3), 7.45–7.58 (m, 2H, 2×CH), 7.66–7.77
(m, 2H, 2×CH), 14.74 (s, 1H, NH, D2O exchange-
able). Anal. Calcd for C11H8FN5S2: C, 45.04; H, 2.75;
N, 23.87. Found: C, 45.25; H, 2.97; N, 23.91.
4-Cyclohexyl-5-(4-methyl-1,2,3-thiadiazol-5-yl)-s-
triazole-3-thione (40). Yield 41%, mp 242–244◦C;
IR (KBr, ν in cm−1): 3252 (NH), 2852, 1476, 730
(Aliph.), 1624 (C N), 1248 (C S); 1H NMR: δ
0.89–1.94 (10H, 5×CH2), 2.66 (s, 3H, CH3), 4.19
(s, 1H, CH), 14.31 (s, 1H, NH, D2O exchangeable).
Anal. Calcd for C11H15N5S2: C, 46.95; H, 5.37; N,
24.89. Found: C, 46.58; H, 5.44; N, 24.70.
4-(2-Fluorophenyl)-5-(pyrrol-2-yl)-s-triazole-3-thi-
one (29). Yield 91%, mp 240–242◦C; IR (KBr, ν in
cm−1): 3273 (NH), 3089, 1510, 1449, 732 (ArH), 1607
1
(C N), 1335 (C S); H NMR (300 MHz, DMSO-d6):
δ 5.29–5.32 (m, 1H, CH), 5.95–5.98 (m, 1H, CH),
6.92–6.94 (m, 1H, CH), 7.43–7.73 (m, 4H, 4×CH),
11.87, 14.06 (2s, 2H, 2×NH, D2O exchangeable).
Anal. Calcd for C12H9FN4S: C, 55.37; H, 3.49; N,
21.52. Found: C, 54.98; H, 3.77; N, 21.30.
4-Butyl-5-(4-methyl-1,2,3-thiadiazol-5-yl)-s-tria-
zole-3-thione (41). Yield 46%, mp 123–125◦C; IR
(KBr, ν in cm−1): 3290 (NH), 2952, 2918, 2869,
Heteroatom Chemistry DOI 10.1002/hc