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Paper | Regular issue | Vol 36, No. 3, 1993, pp.485-495
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6159
Anomalous ‘Lossen-Type’ Rearrangement Synthesis of Functionalized Imidazolinones

Dee Ann Casteel,* Rebecca S. Gephart, and Tracey Morgan

*Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City, Iowa 52242, U.S.A.

Abstract

Reaction of an imidazolinone N-sulfonyloxyimide (3) with ammonia or methylamine provided carboxy-ureido compounds (4, 5, 6, and 7), products of a Lossen rearrangement in which the intermediate isocyanate is trapped by the amine. Possible mechanism(s) are discussed. Upon heating, the carboxy-ureido materials eliminate urea to form the carboxy substituted imidazolones (8, 9, 10).