STUDIES WITH MALONONITRILE DERIVATIVES: SYNTHESIS AND REACTIVITY OF 4-BENZYLFYRAZOLE-3,5-DIAMINE, 4-BENZYLISOXAZOLE-3,5-DIAMINE AND THIAZOLIDIN-3-PHENYLPROPANENITRILE

摘要

Benzylmalononitrile 6 reacts with hydrazines, and hydroxylamine hydrochloride to yield the 4-benzylpyrazole-3,5-diamines 7 and 4-benzylisoxazol-e-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-phenylpropanenitri-le 31.