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Synlett 2008(9): 1391-1393  
DOI: 10.1055/s-2008-1072767
LETTER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of 2-Substituted Benzoxazoles via Beckmann Rearrangement of 2-Hydroxyaryl Ketoximes Using Diethyl Chlorophosphate

A. R. Sardarian*, Z. Shahsavari-Fard
Chemistry Department, College of Science, Shiraz University, Shiraz 71454, Iran
Fax: +98(711)2286008; e-Mail: sardarian@ susc.ac.ir;
Further Information

Publication History

Received 21 August 2007
Publication Date:
07 May 2008 (online)

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Abstract

An efficient method for synthesis of 2-substituted benz­oxazoles has been developed using diethyl chlorophosphate. 2-Hydroxyaryl ketoximes are efficiently converted to benzoxazoles by heating in the presence of diethyl chlorophosphate via Beckmann rearrangement of ketoxime in excellent yields. This method avoids the use of strong acids, harsh conditions, and long reaction times.

Key words

benzoxazoles - Beckmann rearrangement - cyclization - 2-hydroxyaryl ketoximes - diethyl chlorophosphate

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