6-Substituted-2H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-3-thiones
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1642, 1597, 1571, 1467, 1381, 1225, 1036, 957, 917, 828, 682, 603, 495, 473;
1H NMR (CDCl3) δ 1.93, 1.97, 1.98, 2.05 (4s, 12H, CH3CO), 3.75 (ddd, 1H,
J H-5 -H-6 = 2.1Hz, J H-5 -H-6 = 4.8 Hz, J H-5 -H-4 = 9.9 Hz, H-5ꢁ), 4.03 (dd, 1H,
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J H-6 -H-5 = 2.1Hz, J H-6 -H-6 = 12.6 Hz, H-6ꢁ), 4.16 (dd, 1H, J H-6 -H-5 = 4.8
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Hz, J H-6 -H-6 = 12.6 Hz, H-6ꢁꢁ), 5.07 (t, 1H, J H-4 -H-3 = 9.6 Hz, J H-4 -H-5 = 9.9
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Hz, H-4ꢁ), 5.15 (t, 1H, J H-3 -H-2 = 9.3 Hz, J H-3 -H-4 = 9.6 Hz, H-3ꢁ), 5.24 (t,
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1H, J H-2 -H-1 = 9.9 Hz, J H-2 -H-3 = 9.3 Hz, H-2ꢁ), 5.34 (d, 1H, J H-1 -H-2 = 9.9
Hz, H-1ꢁ), 7.49 (td, 2H, J = 2.1, 8.7 Hz, ArH), 7.81 (td, 2H, J = 2.1, 8.7 Hz,
ArH). Anal. Calcd for C23H23ClN4O9S2 (599.0): C, 46.12; H, 3.87; N, 9.35;
S, 10.71. Found: C, 46.08; H, 3.90; N, 9.21; S, 10.70.
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3-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosylthio)-6-(4-nitrophenyl)-[1,2,
4]triazolo[3,4-b][1,3,4]thiadiazole (5d). Yield 576 mg (45%, A), 536 mg
(88%, B); yellow crystals, m.p. 178–180◦C (Rf = 0.14). IR: 3040, 2943, 2889,
2854, 1743, 1605, 1527, 1454, 1373, 1346, 1300, 1223, 1092, 1034, 984, 953,
914, 856, 795, 752, 717, 687, 644, 617, 598, 536, 459, 432; 1H NMR (CDCl3)
δ 1.91 (s, 3 H, CH3CO), 1.960 (s, 3 H, CH3CO), 1.963 (s, 3 H, CH3CO),
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2.04 (s, 3 H, CH3CO), 3.75 (ddd, 1H, J H-5 -H-6 = 2.1Hz, J H-5 -H-6 = 4.8 Hz,
J H-5 -H-4 = 10.2Hz, H-5ꢁ), 4.02 (dd, 1H, J H-6 -H-5 = 2.1Hz, J H-6 -H-6 = 12.6 Hz,
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H-6ꢁ), 4.13 (dd, 1H, J H-6 -H-5 = 4.8 Hz, J H-6 -H-6 = 12.6 Hz, H-6ꢁꢁ), 5.06 (t,
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1H, J H-4 -H-3 = 9.9 Hz, J H-4 -H-5 = 10.2Hz, H-4ꢁ), 5.14 (t, 1H, J H-3 -H-2 = 9.0
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Hz, J H-3 -H-4 = 9.9 Hz, H-3ꢁ), 5.24 (t, 1H, J H-2 -H-1 = 9.9 Hz, J H-2 -H-3 = 9.0
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Hz, H-2ꢁ), 5.33 (d, 1H, J H-1 -H-2 = 9.9 Hz, H-1ꢁ), 8.09 (td, 2H, J = 2.1, 9.0 Hz,
ArH), 8.36 (td, 2H, J = 2.1, 9.0 Hz, ArH). Anal. Calcd for C23H23N5O11S2
(609.6): C, 45.32; H, 3.80; N, 11.49; S, 10.52. Found: C, 45.19; H, 3.96; N,
11.39; S, 10.47.
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2- (2, 3, 4, 6-Tetra - O-acetyl-β -D -glucopyranosyl)-6-phenyl-2H-[1,2,4]tria-
zolo[3,4-b][1,3,4]thiadiazole-3-thione (6a). Yield 119 mg (10%, A); yellow
crystals, m.p. 188–190◦C. IR: 2921, 2853, 1756, 1552, 1525, 1446, 1395,
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1323, 1232, 1036, 1004, 923, 761, 688, 601; H NMR (CDCl3) δ 1.92, 2.02,
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2.07, 2.15 (4 s, 12H, CH3CO), 4.02 (ddd, 1H, J H-5 -H-6 = 2.1Hz, J H-5 -H-6
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4.8 Hz, J H-5 -H-4 = 9.9 Hz, H-5ꢁ), 4.15 (dd, 1H, J H-6 -H-5 = 2.1Hz, J H-6 -H-6
=
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12.6 Hz, H-6ꢁ), 4.31 (dd, 1H, J H-6 -H-5 = 4.8 Hz, J H-6 -H-6 = 12.6 Hz, H-6ꢁꢁ),
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5.23 (t, 1H, J H-4 -H-3 = 9.3 Hz, J H-4 -H-5 = 9.9 Hz, H-4ꢁ), 5.43 (t, 1H, J H-3 -H-2
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= 9.6 Hz, J H-3 -H-4 = 9.3 Hz, H-3ꢁ), 5.72 (t, 1H, J H-2 -H-1 = 9.3 Hz, J H-2 -H-3
=
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9.6 Hz, H-2ꢁ), 6.27 (d, 1H, J H-1 -H-2 = 9.3 Hz, H-1ꢁ), 7.55 (m, 3 H, ArH), 7.90
(td, 2H, J = 1.6, 7.5 Hz, ArH). Anal. Calcd for C23H24N4O9S2 (564.6): C,
48.93; H, 4.28; N, 9.92; S, 11.36. Found: C, 49.09; H, 4.19; N, 9.89; S, 11.39.
2- (2,3,4,6-Tetra-O-acetyl -β-D-glucopyranosyl)-6-(4-aminophenyl)-2H- [1,
2,4]triazolo[3,4-b][1,3,4]thiadiazole-3-thione (6b). Yield 231 mg (19%, A);
yellow crystals, m.p. 116–118◦C, with shrinkage at 90◦C (Rf = 0.5). IR: 3483,
3381, 3029, 2957, 1751, 1607, 1496, 1371, 1229, 1037, 913, 834, 601, 421;
1HN MR (CDCl3) δ 1.90, 2.04, 2.05, 2.14 (4 s, 12H, CH3CO), 4.01 (ddd,
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1H, J H-5 -H-6 = 2.1Hz, J H-5 -H-6 = 4.8 Hz, J H-5 -H-4 = 9.9 Hz, H-5ꢁ), 4.14 (dd,
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