The Journal of Organic Chemistry

Regiospecific synthesis of 3-substituted-5-alkylisoxazoles by modification of the dilithiooxime route to isoxazoles

DH Hoskin, RA Olofson

Index: Hoskin, Dennis H.; Olofson, R. A. Journal of Organic Chemistry, 1982 , vol. 47, # 26 p. 5222 - 5225

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Citation Number: 13

Abstract

A useful regiospecific synthesis of unsymmetrical'isoxazoles from oximes is described in a recent publication from this laboratory. 2 The method is illustrated by the converaion of benzylacetone oxime (1) to the isoxazole (4, 91% overall yield distilled) by deprotonation of 1 with n-BuLi to form the syn-dilithio salt (21, which is acylated by DMF to give 3. The latter subsequently is cyclized to 4 with hot aqueous acid. In a variant of the above route, the ...