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Abstract C-Glycosyl derivatives represent basic structural constituents in a variety of compounds, which are recognized for their antibiotic, antitumoral, and antiplatelet aggregation activities in addition to potential enzyme inhibitory effect. In this investigation, when 3-Carbohydrazide-5-C-(l,4-anhydro-β-D-erythro-tetrofuranosyl)-2-methylfuran (90) was treated with phenylisothiocyanate in absolute ethanol under reflux to afford 1-acetyl-4-phenyl thiosemicarbazide derivative 91 in 80% yield. When the hydrolysis of 91 was carried out under acidic conditions by sulfuric acid, leads to cyclization with sulfur atom to give the 1,2,4-thiadiazole derivative 92 in 60% yield. When the cyclization of 91 was carried out under alkaline conditions, the nucleophilicity of N-4 is enhanced and leads to cyclization with the carbonyl carbon atom to give the 1,2,4-triazole derivative 93 in 75% yield (Scheme 21). |