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Communication | Regular issue | Vol 51, No. 5, 1999, pp.979-982
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8509
The Conversion of Mixed N,O-Diacylated 2-Aminophenols to 2-Substituted Benzoxazoles

Mark R. DeLuca, Irach B. Taraporewala, and Sean M. Kerwin*

*Division of Medicinal Chemistry, College of Pharmacy, The University of Texas at Austin, Austin, Texas 78712-1074, U.S.A.

Abstract

When N,O-diacylated 2-aminophenols that have different acyl substituents on nitrogen and oxygen are treated with p-toluenesulfonic acid in refluxing xylenes, mixtures of benzoxazoles are produced. The major product is the benzoxazole in which the substituent at the 2-position is derived from the acyl group on nitrogen. This product may arise from an unusual case of acid-mediated neighboring amido-group assisted hydrolysis.