282
R. Smiꢀius, M. M. Burbulienꢁ, V. Jakubkienꢁ, E. Udrꢁnaitꢁ, and P. Vainilaviꢀius
Vol 44
Hz (4-6, 4-2), 3J=8 Hz (4-5), 1H, 4-H), 8.03 (dd, 4J=1.7 Hz (6-4,
6-2), 3J=8 Hz (6-5), 1H, 6-H), 8.30 (dd, 4J=1.7 Hz (2-4, 2-6), 1H,
2-H), 14.05 (s, 1H, NH) ppm. Anal. Calcd for C8H7BrN4S
(271.13): C, 35.44; H, 2.60; N, 20.66. Found: C, 35.29; H, 2.53;
N, 20.74.
1.02 (t, J=7.4 Hz, 3H, CH3), 1.78 (sx, J=7.4 Hz, 2H,
CH2CH2CH3), 2.76 (t, J=7.4 Hz, 2H, CH2CH2CH3), 4.77 (s, 2H,
NH2), 12.06 (s, 1H, NH) ppm. Anal. Calcd for C5H10N4S
(158.22): C, 37.96; H, 6.37; N, 35.41. Found: C, 38.15; H, 6.55;
N, 35.11.
4-Amino-5-(4-chlorophenyl)-2,3-dihydro-4H-1,2,4-triazole-
3-thione (2 f). This compound was obtained in 1.98 g (44%)
yield, mp 211-213°C (butylacetate); (m.p.: 210-211°C (ethanol),
Ref. [1]); ir: 3246, 3149, 2935 (NH2, NH), 1638 (NH2), 1598
4-Amino-5-hexyl-2,3-dihydro-4H-1,2,4-triazole-3-thione (2
m). This compound was obtained in 2.4 g (60%) yield, mp 111-
113°C (toluene); ir: 3285, 3152, 2949 (NH2, NH), 1623 (NH2),
1
1564 (C=N), 1485 (C=S) cm-1; H nmr (DMSO-d6): ꢀ 0.91 (t,
1
(C=N), 1498 (C=S) cm-1; H nmr (DMSO-d6): ꢀ 5.81 (s, 2H,
J=7 Hz, 3H, CH3), 1.33-1.38 (m, 6H, CH2CH2CH2CH2CH2CH3),
1.74 (td, J=7.3 Hz, J=15.4 Hz, 2H, CH2CH2CH2CH2CH2CH3),
2.77 (t, J=7.5 Hz, 2H, CH2CH2CH2CH2CH2CH3), 4.70 (s, 2H,
NH2), 11.73 (s, 1H, NH) ppm. Anal. Calcd for C8H16N4S
(200.30): C, 47.97; H, 8.05; N, 27.97. Found: C, 48.17; H, 8.26;
N, 27.69.
NH2), 7.64 (dd, 4J=2.3 Hz (3-5), 3J=8.9 Hz (3-2, 5-6), 2H, 3,5-H2),
8.08 (dd, 4J=2.3 Hz (2-6), 3J=8.9 Hz (2-3, 6-5), 2H, 2,6-H2), 14.00
(s, 1H, NH) ppm. Anal. Calcd for C8H7ClN4S (226.68): C, 42.39;
H, 3.11; N, 24.72. Found: C, 42.54; H, 3.03; N, 24.70.
4-Amino-5-(4-aminophenyl)-2,3-dihydro-4H-1,2,4-triazole-
3-thione (2 g). This compound was obtained in 0.75 g (18%)
yield, mp 258-260°C (methanol); (m.p.: 260-261°C (ethanol),
Ref. [1].); ir: 3352, 3270, 3180, 2928 (NH2, NH), 1612 (NH2),
4-Amino-5-benzyl-2,3-dihydro-4H-1,2,4-triazole-3-thione
(2 n). This compound was obtained in 2.39 g (58%) yield, mp
181-183°C (butylacetate); (m.p.: 179-180°C (ethanol), Ref. [1]);
ir: 3287, 3150, 2935 (NH2, NH), 1624 (NH2), 1567 (C=N), 1495
1
1582 (C=N), 1504 (C=S) cm-1; H nmr (DMSO-d6): ꢀ 5.64 (s,
3
1
(C=S) cm-1; H nmr (DMSO-d6): ꢀ 4.05 (s, 2H, CH2), 5.57 (s,
2H, (C6H4)NH2), 5.72 (s, 2H, NH2), 6.64 (d, J=8.6 Hz (3-2, 5-
6), 2H, 3,5-H2), 7.74 (d, 3J=8.6 Hz (2-3, 6-5), 2H, 2,6-H2), 13.63
(s, 1H, NH) ppm. Anal. Calcd for C8H9N5S (207.25): C, 46.36;
H, 4.38; N, 33.79. Found: C, 46.13; H, 4.43; N, 33.64.
2H, NH2), 7.32 (m, 5H, C6H5), 13.56 (s, 1H, NH) ppm. Anal.
Calcd for C9H10N4S (206.27): C, 52.41; H, 4.89; N, 27.16.
Found: C, 52.23; H, 4.94; N, 26.92.
4-Amino-5-(4-methoxycarbonylphenyl)-2,3-dihydro-4H-
1,2,4-triazole-3-thione (2 h). This compound was obtained in
1.35 g (27%) yield, mp 197-200°C (methanol); ir: 3317, 3108,
2943 (NH2, NH), 1727 (C=O), 1632 (NH2), 1579 (C=N), 1484
4-Amino-5-(6-methyl-2-N-morpholino-4-pyrimidin-yl)-
sulfanylmethyl-2,3-dihydro-4H-1,2,4-triazole-3-thi-one (2 o).
This compound was obtained in 4 g (59%) yield, mp 217-219°C
(butylacetate); ir: 3253, 3130, 2959 (NH2, NH), 1618 (NH2),
1
(C=S), 1285 (COC) cm-1; H nmr (DMSO-d6): ꢀ 3.90 (s, 3H,
1
1553 (C=N), 1505 (C=S), 1119 (COC) cm-1; H nmr (DMSO-
CH3), 5.85 (s, 2H, NH2), 8.10 (dd, 4J=1.7 Hz (3-5), 3J=8.5 Hz (3-
2, 5-6), 2H, 3,5-H2), 8.23 (dd, 4J=1.7 Hz (2-6), 3J=8.5 Hz (2-3, 6-
5), 2H, 2,6-H2), 14.10 (s, 1H, NH) ppm. Anal. Calcd for
C10H10N4O2S (250.27): C, 47.99; H, 4.03; N, 22.39. Found: C,
47.83; H, 3.90; N, 22.58.
d6): ꢀ 2.21 (s, 3H, CH3), 3.64 (t, J=5 Hz, 4H, N(CH2)2), 3.70 (t,
J=5 Hz, 4H, O(CH2)2), 4.43 (s, 2H, SCH2), 5.62 (s, 2H, NH2),
6.56 (s, 1H, CH), 13.63 (s, 1H, NH) ppm. Anal. Calcd for
C12H17N7OS2 (339.43): C, 42.46; H, 5.05; N, 28.89. Found: C,
42.56; H, 4.94; N, 28.84.
4-Amino-5-(3-pyridyl)-2,3-dihydro-4H-1,2,4-triazole-3-thi-
one (2 i). This compound was obtained in 1.35 g (35%) yield,
mp 216-217°C (methanol); ir: 3233, 3149 (NH2, NH), 1653
14-Amino-5-(4,6-dimethyl-2-pyrimidinyl)sulfanyl-methyl-
2,3-dihydro-4H-1,2,4-triazole-3-thione (2 p). This compound
was obtained in 2.58
g (48%) yield, mp 194-197°C
1
(NH2), 1566 (C=N), 1486 (C=S) cm-1; H nmr (DMSO-d6): ꢀ
(butylacetate); ir: 3236, 3118, 2950 (NH2, NH), 1654 (NH2),
5
3
1
1578 (C=N), 1497 (C=S) cm-1; H nmr (DMSO-d6): ꢀ 2.37 (s,
5.83 (s, 2H, NH2), 7.59 (ddd, J=0.9 Hz (5-2), J=4.8 Hz (5-6),
3J=8 Hz (5-4), 1H, 5-H), 8.39 (ddd, J=1.8 Hz (4-6), J=2.2Hz
(4-2), 3J=8 Hz (4-5), 1H, 4-H), 8.74 (dd, 4J=1.7 Hz (6-4),
4
4
6H, (CH3)2), 4.47 (s, 2H, SCH2), 5.62 (s, 2H, NH2), 7.00 (s, 1H,
CH), 13.54 (s, 1H, NH) ppm. Anal. Calcd for C9H12N6S2
(268.35): C, 40.28; H, 4.51; N, 31.32. Found: C, 40.30; H, 4.36;
N, 31.06.
4-Amino-5-(4,6-dimethoxy-2-pyrimidinyl)sulfanyl-methyl-
2,3-dihydro-4H-1,2,4-triazole-3-thione (2 r). This compound
5
4
3J=4.8Hz (6-5), 1H, 6-H), 9.17 (dd, J=0.9 Hz (2-5), J=2.2 Hz
(2-4), 1H, 2-H), 14.08 (s, 1H, NH) ppm. Anal. Calcd for
C7H7N5S (193.23): C, 43.51; H, 3.65; N, 36.24. Found: C, 43.46;
H, 3.58; N, 36.48.
4-Amino-2,3-dihydro-4H-1,2,4-triazole-3-thione (2 j). This
compound was obtained in 1.81 g (78%) yield, mp 169-171°C
(butylacetate); (m.p.: 167-168°C (ethanol), Ref. [20]); ir: 3276,
3172, 2941 (NH2, NH), 1605 (NH2), 1561 (C=N), 1496 (C=S)
was obtained in 2.88
g (48%) yield, mp 158-160°C
(butylacetate); ir: 3263, 3192, 2956 (NH2, NH), 1619 (NH2),
1579 (C=N), 1504 (C=S), 1266, 1051 (COC) cm-1; 1H nmr
(DMSO-d6): ꢀ 3.88 (s, 6H, (CH3O)2), 4.47 (s, 2H, SCH2), 5.63
(s, 2H, NH2), 5.99 (s, 1H, CH), 13.28 (s, 1H, NH) ppm. Anal.
Calcd for C9H12N6O2S2 (300.35): C, 35.99; H, 4.03; N, 27.98.
Found: C, 35.75; H, 4.07; N, 28.22.
1
cm-1; H nmr (DMSO-d6): ꢀ 5.69 (s, 2H, NH2), 8.46 (s, 1H,
CH), 13.65 (s, 1H, NH) ppm. Anal. Calcd for C2H4N4S (116.14):
C, 20.68; H, 3.47; N, 48.24. Found: C, 20.88; H, 3.41; N, 48.13.
4-Amino-5-methyl-2,3-dihydro-4H-1,2,4-triazole-3-thione
(2 k). This compound was obtained in 2 g (77%) yield, m.p.: 208-
210°C (butylacetate); (m.p.: 201-202°C (water), Ref. [20]); ir:
3272, 3116, 2948 (NH2, NH), 1631 (NH2), 1577 (C=N), 1509
(C=S) cm-1; 1H nmr (DMSO-d6): ꢀ 2.25 (s, 3H, CH3), 5.53 (s, 2H,
NH2), 13.41 (s, 1H, NH) ppm. Anal. Calcd for C3H6N4S (130.17):
C, 27.68; H, 4.68; N, 43.04. Found: C, 27.87; H, 4.47; N, 42.95.
4-Amino-5-propyl-2,3-dihydro-4H-1,2,4-triazole-3-thione
(2 l). This compound was obtained in 1.76 g (56%) yield, mp
108-109.5°C (toluene); ir: 3292, 3140, 2942 (NH2, NH), 1625
4-Amino-5-(4-N,N-dimethylamino-6-methyl-2-pyrimidin-
yl)sulfanylmethyl-2,3-dihydro-4H-1,2,4-triazole-3-thione (2
s). This compound was obtained in 2.32 g (39%) yield, mp 225-
227°C (butylacetate); ir: 3284, 3073, 2928 (NH2, NH), 1658
(NH2), 1597 (C=N), 1506 (C=S) cm-1; H nmr (DMSO-d6): ꢀ
1
2.21 (s, 3H, CH3), 3.04 (s, 6H, (CH3)2N), 4.40 (s, 2H, SCH2),
5.61 (s, 2H, NH2), 6.28 (s, 1H, CH), 13.57 (s, 1H, NH) ppm.
Anal. Calcd for C10H15N7S2 (297.40): C, 40.39; H, 5.08; N,
32.97. Found: C, 40.60; H, 5.08; N, 33.00.
4-Amino-5-(6-methyl-4-oxo-3,4-dihydro-2-pyrimidinyl)-
sulfanylmethyl-2,3-dihydro-4H-1,2,4-triazole-3-thione (2 t).
1
(NH2), 1572 (C=N), 1502 (C=S) cm-1; H nmr (DMSO-d6): ꢀ