Preparation of 4,5‐Dihydronaphth[2,1‐c]isoxazoles from Dilithiated 2‐Tetralone Oxime and Select Esters

Abstract

Dilithiated 2‐tetralone oxime, prepared in excess lithium diisopropylamide, was condensed with aromatic esters, such as methyl 4‐methoxybenzoate, followed by cyclization of the C‐acylated intermediate with aqueous acid to give dihydronaphthisoxazoles, 4,5‐dihydronaphth[2,1‐c]isoxazoles.

Keywords:

• acylation–cyclization
• dianion
• dihydronaphthisoxazole
• regioselectivity

Acknowledgments

We thank the following sponsors: the Research Corporation, the National Science Foundation (Grants CHE 9708014 and 0212699) for Research at Undergraduate Institutions, the United States Department of Agriculture (NRICGP 2003‐35504‐12853), and Donors of the Petroleum Research Fund, administered by the American Chemical Society. J. D. Knight received a stipend from the College of Charleston, Summer Undergraduate Research Forum, SURF‐2006.