SYNTHESIS OF SOME N-ALKYLATED 1,2,4-TRIAZOLES, 1,3,4-OXADIAZOLES, AND 1,3,4-THIADIAZOLES BASED ON N-(FURAN-2-YLMETHYLIDENE)-4,6-DIMETHYL-1<i>H</i>-PYRAZOLO- [3,4-<i>b</b>]PYRIDIN-3-AMINE

Abstract

N-(Furan-2-ylmethylidene)-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-amine was prepared and alkylated with the appropriate halo compounds to afford N-alkylated products. 2-[3-(Furan-2-ylmethylideneamino)-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 conditions to give 1,2,4-triazole, 1,3,4-oxadiazole, and 1,3,4-thiadiazole derivatives. Condensation of the hydrazide with monosaccharide aldoses gave the corresponding sugar hydrazones, which on treatment with acetic anhydride readily undergo cyclization reaction to afford oxadiazoline derivatives.

How to Cite
El-Essawy, F. A.; Rady, S. I. M. Chem. Heterocycl. Compd. 2011, 47(4), 497. [Khim. Geterotsikl. Soedin. 2011, 602.]

For this article in the English edition see DOI 10.1007/s10593-011-0787-z