Copper-Catalyzed Domino Annulation Approaches to the Synthesis of Benzoxazoles under Microwave-Accelerated and Conventional Thermal Conditions

Russell D. Viirre, Ghotas Evindar and Robert A. Batey

*Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6, Email: rbateychem.utoronto.ca

R. D. Viirre, G. Evindar, R. A. Batey, J. Org. Chem., 2008, 73, 3452-3459.

DOI: 10.1021/jo702145d (free Supporting Information)

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Abstract

A versatile one-pot domino acylation annulation reaction of 2-bromoanilines with acyl chlorides in the presence of Cs₂CO₃, catalytic CuI, and 1,10-phenanthroline under microwave conditions was applied to the synthesis of benzoxazoles. These copper-catalyzed approaches complement existing strategies for benzoxazole synthesis, which typically utilize 2-aminopheonls as precursors.

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Parallel Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides

G. Evindar, R. A. Batey, J. Org. Chem., 2006, 71, 1802-1808.

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Key Words

Benzoxazoles, Microwave Synthesis

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ID: J42-Y2008-1140