Base??induced ring cleavage of 4??functionalized??3??unsubstituted isoxazoles. Synthesis of 5??aminoazoles and 4??cyanoazoles

A Alberola, LF Antolin, AM Gonzalez…

Index: Alberola; Antolin; Gonzalez; et al. Journal of Heterocyclic Chemistry, 1986 , vol. 23, # 4 p. 1035 - 1038

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Citation Number: 18

Abstract

In a previous paper we described that 3-unsubstituted isoxazoles bearing electron-accepting groups at C-4 under- went ring cleavage when treated with organic bases leading to stable p-cyanoenolates [2]. As is shown in the present article, the ability of these enolates to be con- verted into 5-aminoisoxazoles or 5-aminopyrazoles is one of the most interesting features of this work. Much of our recent investigations have been directed to the synthesis of 5- ...