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Abstract Boiling of the thiosemicarbazide derivative 1 in 2N NaOH solu-tion at refluxing temperature afforded the 1,2,4-triazole derivative 2 in 81% yield. Alkylation of the 1,2,4-triazole thioles/thiones 2 with methyl or ethyl iodide in alkaline medium afforded the corresponding S-methyl or Sethyl derivatives 3a,b in 76% and 79% yields, respectively. Hydrazinolysis of 3a and 3b gave 4 in 80% yields When the hydrazide 6 was allowed to react with D-galactose and Darabinose in an aqueous ethanolic solution and in the presence of a catalytic amount of acetic acid, the corresponding sugar hydrazones 7a,b were obtained in 72 78% yields. Reaction of the sugar hydrazones 7a,b with acetic anhydride in pyridine at room temperature afforded the per- O-acetylated derivatives 8a,b in 77-80% yields. On the other hand, when the sugar hydrazones 7a,b were allowed to react with acetic anhydride at 100 °C the sugar substituted 1,3,4-oxadiazoline derivatives 9a,b were obtained in in 62 69% yields. |