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Paper | Regular issue | Vol 75, No. 6, 2008, pp.1371-1383
Published online, 15th February, 2008
DOI: 10.3987/COM-07-11307
Studies with Malononitrile Derivatives: Synthesis and Reactivity of 4-Benzylpyrazole-3,5-diamine, 4-Benzylisoxazole-3,5-diamine and Thiazolidin-3-phenylpropanenitrile

Saleh Mohammed Al-Mousawi,* Moustafa Sherief Moustafa, and Mohamed Hilmy Elnagdi

*Department of Chemistry, Faculty of Science, University of Kuwait: P.O. Box 5969, Safat: 13060 Kuwait

Abstract

Benzylmalononitrile 6 reacts with hydrazines, and hydroxylamine hydrochloride to yield the 4-benzylpyrazole-3,5-diamines 7 and 4-benzylisoxazole-3,5-diamine 9, respectively. Pyrazole-3,5-diamines 7 could be readily reacted with α,β-unsaturated nitriles to yield pyrazolo[1,5-a]pyrimidines 20. Benzylmalononitrile, also reacted with thioglycolic acid to yield tautomeric mixture of 2-(4-hydroxythiazol-2-yl)-3-phenylpropanenitrile 29 and 2-(4-oxothiazolidin-2-yl)-3-phenylpropanenitrile 30 that coupled with benzene diazonium chloride to yield 2-(4-oxo-5-(phenylhydrazono)-thiazolidin-2-ylidene)-3-phenylpropanenitrile 31.