SYNTHESIS AND ANTIMICROBIAL ACTIVITY
319
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1714, 1665, 1594, 1385. H NMR spectrum, δ, ppm:
(1H), 7.54–7.58 m (1H), 7.60–7.67 m (1H), 7.75–7.82
m (1H), 7.91–8.00 m (2H), 8.03–8.06 d.d (J =
2.25 Hz, J = 2.00 Hz, 1H), 8.09 s (1H), 8.14–8.16 d
(J = 8.28 Hz, 1H), 8.22 s (1H), 8.69 s (1H). 13C NMR
spectrum, δ, ppm: 13.9, 41. 8, 44.1, 110.4, 111.0,
113.8, 118.4, 120.9, 121.7, 123.2, 125.4, 25.5, 126.1,
127.4, 127.2, 128.0, 129.7, 131.0, 131.4, 131.9, 135.5,
135.2, 137.5, 144.5, 151.4, 165.3, 169.2. ESI-MS: m/z
594 [M + 1]. C30H22N6O6S.
2.27 s (3H), 4.93 s (2H), 5.65 s (2H), 7.30–7.39 m
(2H), 7.44–7.58 m (3H), 7.58 d (J = 6.76 Hz, 2H), 7.61
d (J = 9.03 Hz, 2H), 7.86 d (J = 9.26 Hz, 1H), 8.05 d
(J = 10.03 Hz, 1H), 8.19 s (1H), 8.20 s (1H), 8.26 s
(1H). 13C NMR spectrum, δ, ppm: 3.8, 41.4, 43.9,
110.1, 111.3, 113.9, 118.8, 121.7, 123.5, 123.8, 125.7,
126.1, 127.5, 127.9, 128.3, 128.7, 131.0, 131.9, 136.0,
137.4, 142.8, 143.2, 146.9, 150.6, 165.2, 167.0. ESI-
MS: m/z 595 [M + 2]. C29H21N7O6S.
(Z)-5-{(1-[(1-(2-Methyl-3-nitrophenyl)-1H-1,2,3-
triazol-4-yl)methyl]-1H-indol-3-yl)methylene}-3-(2-
nitrobenzyl)thiazolidine-2,4-dione (6e). Yield 85%,
mp 232–234°C. IR spectrum, ν, cm–1: 3016, 2970,
(Z)-3-(4-Bromobenzyl)-5-{(1-[(1-(2-methyl-3-nitro-
phenyl)-1H-1,2,3-triazol-4-yl)methyl]-1H-indol-3-yl)-
methylene}thiazolidine-2,4-dione (6b) Yield 85%,
mp 242–244°C. IR spectrum, ν, cm–1: 3103, 1719, 1668,
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2223, 1737, 1685, 1523, 1348. H NMR spectrum, δ,
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1598, 1385. H NMR spectrum, δ, ppm: 2.10 s (3H),
ppm: 2.23 s (3H), 5.15 s (2H), 5.66 s (2H), 7.30–7.32
m (1H), 7.33–7.35 m (1H), 7.37–7.39 m (2H), 7.40–
7.42 d.d (J = 1.00 Hz, J = 1.00 Hz, 1H), 7.46–7.50 m
(2H), 7.52–7.54 d.d (J = 1.75 Hz, J =1.25 Hz, 1H),
7.56 s (1H), 7.58 s (1H), 7.68–7.70 d.d (, J = 1.50 Hz,
J = 1.25 Hz, 1H), 7.84–7.86 d (J = 8.28 Hz, 1H), 8.00–
8.03 d.d (J = 2.00 Hz, J = 1.50 Hz, 1H), 8.280 s (1H).
ESI-MS: m/z 595 [M + 2]. C29H21N7O6S.
4.82 s (2H), 5.80 s (2H), 7.23–7.35 m (4H), 7.56 d.d
(J = 2.00 Hz, J = 2.00 Hz, 2H), 7.65 (t, J = 1.25 Hz,
1H), 7.76 d (J = 8.28 Hz, 1H), 7.81 d.d (J = 1.50 Hz,
J = 1.25 Hz, 1H), 7.96 d (J = 8.03 Hz, 1H), 8.08 s
(1H), 8.15 d.d (J = 1.50 Hz, J=1.25 Hz, 1H), 8.20 s
(1H), 8.67 s (1H). 13C NMR spectrum, δ, ppm: 13.8,
41.3, 43.8, 110.1, 111.3, 113.9, 118.7, 120.9, 121.7,
123.4, 125.5, 125.6, 126.1, 127.4, 128.3, 129.8, 131.0,
131.5, 131.7, 135.1, 135.9, 137.4, 142.9, 150.5,
165.3,166.9. ESI-MS: m/z 629 [M + 1]. C29H21N7O4S.
(Z)-3-(2-Fluorobenzyl)-5-{(1-[(1-(2-methyl-3-nitro-
phenyl)-1H-1,2,3-triazol-4-yl)methyl]-1H-indol-3-yl)-
methylene}thiazolidine-2,4-dione (6f). Yield 89%,
mp 233–234°C. IR spectrum, ν, cm–1: 3144, 2970, 1739,
(Z)-3-(4-Fluorobenzyl)-5-{(1-[(1-(2-methyl-3-nitro-
phenyl)-1H-1,2,3-triazol-4-yl)methyl]-1H-indol-3-yl)-
methylene}thiazolidine-2,4-dione (6c). Yield 90%,
mp 245–247°C. IR spectrum, ν, cm–1: 3143, 2955,
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1721, 1666, 1598, 1350, 825. H NMR spectrum, δ,
ppm: 2.23 s (3H), 5.00 s (2H), 5.65 s (2H), 7.03–7.08
m (2H), 7.10–7.12 m (1H), 7.32 d.d (J = 1.00 Hz, J =
1.25 Hz, 1H), 7.34–7.38 m (2H), 7.46–7.50 m (2H),
7.51 (t, J = 1.25, 1H), 7.54 s (1H), 7.56 s (1H), 7.83–
7.58 d.d (J =1.00 Hz, J = 1.25 Hz, 1H), 8.00–7.02 d.d
(J = 2.00 Hz, J = 1.75 Hz, 1H), 8.25 s (1H). ESI-MS:
m/z 568 (M+ 1). C29H21FN6O4S.
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1720, 1668, 1597, 1365. H NMR spectrum, δ, ppm:
2.22 s (3H), 4.86 s (2H), 5.64 s (2H), 6.91–7.04 m
(2H), 7.30 d.d (J = 1.25 Hz, J = 1.00 Hz, 1H), 7.34–
7.37 m (2H), 7.43–7.46 m (1H), 7.47 d (J = 4.51 Hz,
1H), 7.49 d (J = 4.01 Hz, 1H), 7.45 d (J = 2.008 Hz,
1H), 7.54 s (1H), 7.84 d.d (J = 2.00 Hz, J = 1.50Hz,
1H), 8.01 d.d (J = 2.25 Hz, J = 2.00 Hz, 1H), 8.23 s
(1H). 13C NMR spectrum, δ, ppm: 13.2, 41.2, 43.8,
110.1, 111.0, 113.8, 118.4, 120.9, 121.7, 123.2, 125.4,
25.5, 126.1, 127.4, 127.2, 128.0, 129.7, 131.0, 131.4,
131.9, 135.5, 135.2, 137.5, 142.8, 150.8, 166.2170.1.
ESI-MS: m/z 568 [M + 1]. C29H21FN6O4S.
(Z)-3-(2-Chlorobenzyl)-5-{(1-[(1-(2-methyl-3-nitro-
phenyl)-1H-1,2,3-triazol-4-yl)methyl]-1H-indol-3-yl)-
methylene}thiazolidine-2,4-dione (6g). Yield 82%,
mp 242–243°C. IR spectrum, ν, cm–1: 3111, 2970,
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1735, 1677, 1597, 1346, 1034. H NMR spectrum, δ,
ppm: 2.23 s (3H), 5.06 s (2H), 5.66 s (2H), 7.15–7.19
m (2H), 7.21–7.24 m (1H), 7.32–7.35 m (1H), 7.37–
7.40 m (1H), 7.46–7.52 m (2H), 7.55 s (1H), 7.60 s
(1H), 7.60–7.63 m (1H), 7.86 d (J = 8.28 Hz, 1H), 8.01
d (J = 8.78 Hz, 1H), 8.24 d (J = 8.78 Hz, 1H), 8.26 s
(1H). 13C NMR spectrum, δ, ppm: 13.8, 41.3, 43.8,
110.1, 111.3, 113.9, 118.7, 120.9, 121.1, 121.8, 123.9,
125.5, 25.6, 126.1, 127.4, 127.9, 128.3, 129.8, 131.0,
131.5, 131.7, 135.1, 135.9, 137.4, 142.9, 150.5, 164.2,
166.6. ESI-MS: m/z 585 [M + 1]. C29H21ClN6O4S.
(Z)-4-{(5-[(1-{[1-(2-Methyl-3-nitrophenyl)-1H-1,2,3-
triazol-4-yl]methyl}-1H-indol-3-yl)methylene]-2,4-di-
oxothiazolidin-3-yl)methyl}benzoic acid (6d). Yield
92%, mp 166–167°C. IR spectrum, ν, cm–1: 2924, 2853,
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1714, 1675, 1527, 1349, 1115, 1012. H NMR spec-
trum, δ, ppm: 2.10 s (3H), 4.28 s (1H), 4.30 s (1H),
4.76 s (1H), 4.93 d (J = 8.533 Hz, 1H), 5.43–5.46 m
(2H), 7.24–7.35 m (1H), 5.80 s (1H), 7.41–7.45 m
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 2 2017