4-[1-(4-Bromophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-N-(4-methylphenyl)-1,3-thiazole-2-amine (3d).
Yield 76%, cream-colored crystals, mp 209-210°С. IR spectrum, ν, cm-1: 3360, 1611, 1536, 1443, 1317, 1239,
1065, 1006, 830, 503. 1H NMR spectrum, δ, ppm (J, Hz): 2.25 (3H, s, ArCH3); 2.66 (3H, s, HetCH3); 7.12 (2H,
d, J = 6.9, H Ar); 7.25 (1H, s, H-5 thiazole); 7.58 (2H, d, J = 7.3, H Ar); 7.65 (2H, d, J = 7.3, H Ar); 7.84 (2H,
13
d, J = 7.3, H Ar); 10.24 (1H, s, NH). C NMR spectrum, δ, ppm: 10.1 (HetCH3); 20.8 (ArCH3); 104.0 (C-5
thiazole); 117.5 (CH Ar); 123.2 (C Ar); 127.7 (CH Ar); 129.8 (CH Ar); 130.6 (C Ar); 131.1 (C Ar); 133.1
(CH Ar); 135.6 (C triazole); 139.2 (C Ar); 140.6 (C triazole); 143.0 (C-4 thiazole); 164.4 (C-2 thiazole). Found,
%: C 53.61; H 3.83; N 16.51. C19H16BrN5S. Calculated, %: С 53.53; H 3.78; N 16.43.
4-[1-(4-Bromophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-N-(3-methylphenyl)-1,3-thiazole-2-amine (3e).
Yield 78%, cream-colored crystals, mp 211-212°С. IR spectrum, ν, cm-1: 3356, 1608, 1542, 1525, 1495, 1309,
1070, 1005, 835, 552. 1H NMR spectrum, δ, ppm (J, Hz): 2.29 (3H, s, ArCH3); 2.70 (3H, s, HetCH3); 6.78 (1H,
d, J = 7.3, H Ar); 7.19 (1H, t, J = 7.8, H Ar); 7.28 (1H, s, H-5 thiazole); 7.37 (1H, d, J = 8.2, H Ar); 7.66 (2H, d,
13
J = 8.2, H Ar); 7.70 (1H, s, H Ar); 7.82-7.89 (2H, m, H Ar); 10.28 (1H, s, NH). C NMR spectrum, δ, ppm:
10.1 (HetCH3); 21.8 (ArCH3); 104.2 (C-5 thiazole); 114.6 (CH Ar); 117.9 (CH Ar); 122.5 (CH Ar); 127.7 (CH
Ar); 129.2 (CH Ar); 131.1 (C Ar); 133.1 (CH Ar); 133.2 (C triazole); 135.6 (C Ar); 138.6 (C Ar); 140.6
(C triazole); 141.5 (C Ar); 142.9 (C-4 thiazole); 164.2 (C-2 thiazole). Found, %: C 53.59; H 3.82; N 16.48.
C19H16BrN5S. Calculated, %: С 53.53; H 3.78; N 16.43.
N-{4-[1-(4-Bromophenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-1,3-thiazole-2-yl}pyridine-2-amine
(3f).
Yield 79%, white crystals, mp 245-246°С. IR spectrum, ν, cm-1: 3323, 1608, 1536, 1496, 1415, 1299, 1069,
1005, 832, 771. 1H NMR spectrum, δ, ppm (J, Hz): 2.67 (3H, s, CH3); 7.12 (1H, d, J = 8.3, H-3 Py); 7.37 (1H, s,
H-5 thiazole); 7.62 (1H, d, J = 8.6, H-5 Py); 7.65-7.67 (2H, m, H Ar); 7.70-7.75 (1H, m, H-4 Py); 7.86 (2H, d,
J = 8.7, H Ar); 8.33 (1H, d, J = 5.0, H-6 Py); 11.38 (1H, s, NH). 13C NMR spectrum, δ, ppm: 10.2 (CH3); 107.4
(C-5 thiazole); 111.3 (CH Py); 116.5 (CH Py); 127.7 (CH Ar); 130.1 (CH Ar); 131.1 (C Ar); 134.7 (C triazole);
135.7 (C Ar); 138.4 (CH Py); 140.7 (C triazole); 141.8 (C-4 thiazole); 146.9 (CH Py); 152.2 (C-2 Py); 160.3
(C-2 thiazole). Found, %: C 49.46; H 3.21; N 20.41. C17H13BrN6S. Calculated, %: С 49.40; H 3.17; N 20.33.
4-[5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl]-N-(4-methylphenyl)-1,3-thiazole-2-amine (3g).
Yield 85%, yellow crystals, mp 183-184°С. IR spectrum, ν, cm-1: 3371, 1614, 1597, 1545, 1526, 1346, 1119,
858. 1H NMR spectrum, δ, ppm (J, Hz): 2.25 (3H, s, ArCH3); 2.75 (3H, s, HetCH3); 7.13 (2H, d, J = 8.1, H Ar);
7.29 (1H, s, H-5 thiazole); 7.57 (2H, d, J = 8.3, H Ar); 8.02 (2H, d, J = 8.9, H Ar); 8.48 (2H, d, J = 8.9, H Ar);
10.25 (1H, s, NH). 13C NMR spectrum, δ, ppm: 10.3 (HetCH3); 20.8 (ArCH3); 104.4 (C-5 thiazole); 117.5
(CH Ar); 125.6 (CH Ar); 126.4 (CH Ar); 129.8 (CH Ar); 130.7 (C Ar); 131.3 (C triazole); 139.1 (C Ar); 141.0
(C Ar); 141.2 (C triazole); 142.7 (C-4 thiazole); 147.9 (C Ar); 164.5 (C-2 thiazole). Found, %: C 58.22; H 4.17;
N 21.48. C19H16N6O2S. Calculated, %: С 58.15; H 4.11; N 21.41.
4-[5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl]-N-(3-methylphenyl)-1,3-thiazole-2-amine (3h).
Yield 93%, yellow crystals, mp 227-229°С. IR spectrum, ν, cm-1: 3374, 1613, 1595, 1549, 1527, 1343, 1189,
1088, 1004, 857, 774, 688. 1H NMR spectrum, δ, ppm (J, Hz): 2.30 (3H, s, ArCH3); 2.79 (3H, s, HetCH3); 6.78
(1H, d, J = 7.2, H Ar); 7.19 (1H, t, J = 7.7, H Ar); 7.32 (1H, s, H-5 thiazole); 7.37 (1H, d, J = 7.6, H Ar); 7.70
(1H, s, H Ar); 8.02 (2H, d, J = 8.9, H Ar); 8.48 (2H, d, J = 8.9, H Ar); 10.30 (1H, s, NH). 13C NMR spectrum, δ,
ppm: 10.3 (HetCH3); 21.8 (ArCH3); 104.6 (C-5 thiazole); 114.6 (CH Ar); 118.0 (CH Ar); 122.5 (CH Ar); 125.5
(CH Ar); 126.4 (CH Ar); 129.2 (CH Ar); 131.3 (C triazole); 138.6 (C Ar); 141.0 (C Ar); 141.2 (C triazole);
141.5 (C Ar); 142.6 (C-4 thiazole); 147.9 (C Ar); 164.3 (C-2 thiazole); Found, %: C 58.19; H 4.16; N 21.51.
C19H16N6O2S. Calculated, %: С 58.15; H 4.11; N 21.41.
N-{4-[5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl]-1,3-thiazol-2-yl}pyridine-2-amine (3i). Yield
92%, yellow crystals, mp >300°С (decomp.). IR spectrum, ν, cm-1: 3389, 1607, 1534, 1502, 1481, 1344, 1149,
1
921, 858. H NMR spectrum, δ, ppm (J, Hz): 2.76 (3H, s, CH3); 6.95 (1H, t, J = 6.2, H-3 Py); 7.13 (1H, d,
J = 8.3, H-5 Py); 7.42 (1H, s, H-5 thiazole); 7.71-7.76 (1H, m, H-4 Py); 8.03 (2H, d, J = 8.9, H Ar); 8.33 (1H, d,
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J = 4.9, H Py); 8.48 (2H, d, J = 8.8, H Ar); 11.42 (1H, s, NH). C NMR spectrum, δ, ppm: 10.4 (CH3); 107.9
(C-5 thiazole); 111.4 (CH Py); 116.7 (CH Py); 125.6 (CH Ar); 126.4 (CH Ar); 131.3 (C triazole); 138.5
1030