Studies on Nucleoside Analogs. XXI. : A Convenient Synthesis of 1, 2, 4-Triazole-5-thione Glycosides

抄録

The reaction of glycosyl isothiocyanates (1a-c) with acyl or aroyl hydrazine, followed by treatment with Ac₂O-H₃PO₄, afforded 1, 2, 4-triazole-5-thione glycosides (20a, 21a-c, 22a) in fair yields. Attempts to prepare 1, 2, 4-triazole glycoside analogs with acetic anhydride or sodium methoxide failed. The reaction of glycosyl-2-(phenyl-or pyrid-2-ylhydrazine) thiocarboxamides (6a, 7a) with phosgene in pyridine or triethylamine gave thiadiazole-5-thiones (8a, 9a) instead of 1, 2, 4-triazole glycosides.