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DOI: 10.1039/A907527E (Paper) Reference Section for: Chem. Commun., 1999, 2273-2274

First synthesis of bis[1,2,3]triazolo[1,5-b;5′,1′-f][1,3,6]thiadiazepine derivatives by [2+1] condensation of 1,2,3-thiadiazoles with vicinal diamines

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Natalya N. Volkova, Evgeniy V. Tarasov, Vasiliy A. Bakulev and Wim Dehaen

Abstract

Novel bistriazolo[1,3,6]thiadiazepine derivatives have been prepared by the base-catalyzed condensation of aromatic and aliphatic 1,2-diamines with 5-chloro-1,2,3-thiadiazoles, via a multistep process which is thought to involve two Dimroth rearrangements and subsequent loss of hydrogen sulfide by intramolecular nucleophilic substitution.

References

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  5. Selected data for 5a: mp 164 °C, δH(CDCl3) 1.48 (6H, t, J 7.1, CH3), 4.51 (4H, q, J 7.1, CH2), 7.79–7.81 (2H, m, CH-arom), 8.08–8.11 (2H, m, CH-arom); δC(CDCl3) 14.2 (CH3), 62.1 (CH2), 126.3 (4,5 CH arom.), 128.2 (1,2-C arom.), 131.4 (3,6 CH arom.), 134.5 (C-5 triazole), 139.7 (C-4 triazole), 159.2 (CO); m/z 386 (M+., 25), 258 (M+.– CO2Et – 2N2, 83), 214 (M+.– 2CO2Et – N2, 71), 186 (M+.– 2CO2Et–2N2, 100)(calcd. for C16H16N6O4S: C, 49.74; H, 3.65; N, 21.75; S, 8.30. Found: C, 49.33; H, 3.99; N, 21.59; Sl 8.32%). For 7: mp 253 °C; δH(DMSO-d6) 7.87–7.94 (2H, m, CH-arom.), 8.06–8.14 (2H, m, CH-arom.), 8.17 (2H, s, 2CH); δC(DMSO-d6) 126.1 (4,5-CH arom.), 127.8 (C5 triazole), 130.0 (1,2-C arom.), 131.3 (3,6-CH arom.), 135.6 (C4 triazole); m/z 242 (M+., 61), 186 (M+. – 2N2, 100), 102 (C7H4N+, 76), 76 (C6H4+., 52)(calcd. for C10H6N6S: C, 49.58; H, 2.50; N, 34.69; S, 8.30. Found: C, 49.68; H, 2.81; N, 34.43; S, 8.32%).
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