Synthesis of some N-alkylated 1,2,4-triazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles based on N-(furan-2-yl-methylidene)-4,6-dimethyl-1H-pyrazolo-[3,4-b]pyridine-3-amine

被引:0
作者
F. A. El-Essawy
S. I. M. Rady
机构
[1] Menoufia University,Chemistry Department, Faculty of Science
来源
Chemistry of Heterocyclic Compounds | 2011年 / 47卷
关键词
aldoses; 1,3,4-oxadiazole; pyrazolopyridine; 1,3,4-thiadiazole; thiosemicarbazide; 1,2,4-triazole; cyclization;
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摘要
N-(Furan-2-ylmethylidene)-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-amine was prepared and alkyla- ted with the corresponding halo compounds to afford N-alkylated products. 2-[3-(Furan-2-ylmethy- lideneamino)-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-1-yl]acetohydrazide was converted into the key intermediate thiosemicarbazide, which undergoes cyclization reactions under acidic and basic conditi- ons to give 1,2,4-triazole, 1,3,4-oxadiazole, and 1,3,4-thiadiazole derivatives. Condensation of the hyd- razide with monosaccharide aldoses gave the corresponding sugar hydrazones, which on treatment with acetic anhydride readily undergo cyclization reaction to afford oxadiazoline derivatives.
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页码:497 / 506
页数:9
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