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

Mina Tamura; Yumiko Ise; Yoshikazu Okajima; Nagatoshi Nishiwaki; Masahiro Ariga

doi:10.1055/s-2006-950210

PAPER

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

Mina Tamura, Yumiko Ise, Yoshikazu Okajima, Nagatoshi Nishiwaki*, Masahiro Ariga*
Department of Chemistry, Osaka Kyoiku University, Asahigaoka 4-698-1, Kashiwara, Osaka 582-8582, Japan
Fax: +81(72)9783399; e-Mail: nishi@cc.osaka-kyoiku.ac.jp;

Abstract

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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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