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Synthesis 2012(4): 551-560  
DOI: 10.1055/s-0031-1289684
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Synthesis of 1,4-Disubstituted Imidazolidin-2-ones from Fused-Ring Aziridines

Iwona M. Maciagiewicz, Fang Fang, Dennis A. Roberts, Shu Zhou, Jennifer V. Hines, Stephen C. Bergmeier*
Department of Chemistry and Biochemistry, Clippinger Laboratories, Ohio University, Athens, OH 45701, USA
Fax: +1(740)5930148; e-Mail: bergmeis@ohio.edu;
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Publication History

Received 24 October 2011
Publication Date:
30 January 2012 (online)

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Abstract

As part of an antibacterial drug discovery project, we were interested in preparing bioisosteric replacement analogues of 4,5-disubstituted oxazolidinones. One such isosteric replacement is the imidazolidinone ring system. Here, we report the development of a general synthesis of 1,4-disubstituted imidazolidinones that takes advantage of the base-catalyzed rearrangement of amino­methyl-substituted oxazolidinones.

Key words

drug discovery - fused-ring systems - ring opening - rearrangements

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