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Note | Regular issue | Vol 75, No. 5, 2008, pp.1199-1203
Published online, 18th January, 2008
DOI: 10.3987/COM-07-11282
Diels-Alder Reactions of a Styrene-Isocyanate: Unexpected Formation of a Pyridinone and Uracil

Gregory A. Gfesser,* David Whittern, Marlon D. Cowart, and Ramin Faghih

*Neuroscience Research, Global Pharmaceutical Research and Development, Abbott Laboratories, 100 Abbott Park Road, Abbott Park, IL 60064, USA

Abstract

During the preparation of 6-bromoisoquinolinone, a novel and unexpected reaction occurred to form a pyridinone and a pyrimidine-2,4-dione. We propose a [4+2] Diels-Alder dimerization of an intermediate styrene-isocyanate to explain the observed products.