Nucleophilic opening of a bicyclic aziridine: Synthesis of oxazolidinones and aziridinylureas

ORGN 673

Jeffrey A. Frick1, Stephen C. Bergmeier2, Jungfeng Huang2, Steven J. Katz2, Nicholas J. Van Malderen2, and Scott M. Brombosz1. (1) Department of Chemistry, Illinois Wesleyan University, P.O. Box 2900, Bloomington, IL 61702-2900, (2) Department of Chemistry and Biochemistry, Ohio University, Athens, OH 45701
The ring opening reaction of 3-oxa-1-azabicyclo[3.1.0]- hexan-2-ones (1) with amines and alcohols was examined. The predominant product of amine opening reactions conducted in dichloromethane was the oxazolidinone (2), although the aziridine (3) formed in some cases. The aziridine (3) is formed preferentially when the reaction is conducted in toluene. Reaction of the bicyclic aziridine with alcohols in the presence of Lewis acids produces the oxazolidinone (2). We will present specific results for the amine and alcohol opening reactions, detailing the scope of reaction and efforts to control product distribution.

 

New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004