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Communication | Special issue | Vol 76, No. 1, 2008, pp.221-225
Published online, 1st May, 2008
DOI: 10.3987/COM-08-S(N)51
A New Synthesis of Dihydropyridin-2-ones from Brassard’s Diene and Imines

Teruaki Mukaiyama,* Yuji Maruyama, and Takayuki Kitazawa

*Center for Basic Research, The Kitasato Institute, 6-15-5 (TCI) Toshima, Kita-ku, Tokyo 114-0003, Japan

Abstract

A new method for the synthesis of dihydropyridin-2-ones from various N-2-nitrobenzenesulfonyl (nosyl) imines and 1,3-diethoxy-1-trimethylsiloxy-1,3-butadiene (Brassard’s diene) under weakly-basic conditions is described. This synthesis of dihydropyridin-2-ones involves the initial addition reaction of Brassard’s diene to imines to afford the adducts followed by a cyclization reaction that forms the corresponding 4-ethoxy-5,6-dihydro-1H-pyridin-2-ones in moderate to good yields after deprotection of its nosyl group from the adducts.