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■ Condensation of 2-Amino-5-chlorobenzoxazole with α-Bromoketones: A Mechanistic Study

Patrick J. Roy,* Kerri Landry, Yves Leblanc, Chun Li, and Nancy Tsou

*Department of Medicinal Chemistry, Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe-Claire-Dorval, Quebec, H9R 4P8, Canada

Abstract

The condensation of 2-aminobenzothiazoles with α-bromo ketones products the fused imidazothiazole (2) whereas the analogous reaction with 2-aminobenzoxazoles gives the unexpected carbamate (10) or the fused imidazooxazole (13), depending on the nature of the starting materials. Isotope labelling studies as well as a proposed mechanism will be discussed.