Facile Synthesis of 3-Carbamoyl-1,2,4-Oxadiazoles

Abstract

A range of 1,2,4-oxadiazoles, having a carbamoyl group at the 3-position, were synthesized from 2-methyl-4-nitroisoxazolin-5(2H)-one via three steps. Ammonolysis of this nitroisoxazol­one afforded 2-amino-2-hydroxyimino-N-methylacetamide in excellent yield. O-Acylation of this key amidoxime, followed by ring closure, proceeded smoothly to give 3-carbamoyl-1,2,4-oxadiazoles having a substituent at the 5-position which could be easily modified by changing the O-acylating agent. Since each step requires only simple manipulations, the synthetic utility of this procedure is concluded to be high.

Key words

O-acylation - 3-carbamoyl-1,2,4-oxadiazoles - heterocycles - nitroisoxazolone - ring closure

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