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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

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Chemistry of Heterocyclic Compounds Aims and scope

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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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt

    F. A. El-Essawy & S. I. M. Rady

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  1. F. A. El-Essawy
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  2. S. I. M. Rady
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Correspondence to F. A. El-Essawy.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 597–601, April, 2011.

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El-Essawy, F.A., Rady, S.I.M. 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. Chem Heterocycl Comp 47, 497–506 (2011). https://doi.org/10.1007/s10593-011-0787-z

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  • DOI: https://doi.org/10.1007/s10593-011-0787-z

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