Preparation of Substituted Imidazolidinones and Hydantoins by Ring-Expansion of Aziridinones

Erach R. Talaty; Mashitah M. Yusoff; S. Asmah Ismail; Jaime A. Gomez; Charles E. Keller; Jean M. Younger

doi:10.1055/s-1997-3256

Synlett 1997; 1997(6): 683-684
DOI: 10.1055/s-1997-3256

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Preparation of Substituted Imidazolidinones and Hydantoins by Ring-Expansion of Aziridinones

Erach R. Talaty^* , Mashitah M. Yusoff, S. Asmah Ismail, Jaime A. Gomez, Charles E. Keller, Jean M. Younger

^*Department of Chemistry, Wichita State University, Wichita, Kansas 67260-0051, U.S.A.

Abstract

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Reaction of 1,3-di-tert-butylaziridinone and other di-tert-alkylaziridinones with cyanamides produces an imidazolidinone (3 or 6) bearing the tert-alkyl substituents at positions 1 and 5 only, by selective cleavage of the acyl-nitrogen bond. Treatment of the product from the unsubstituted cyanamide (3) with HNO₂ furnishes the corresponding hydantoin (5), whereas treatment with alkyl halides and base affords another imidazolidinone (7).

aziridinones - ring-opening - substituted imidazolidinones - hydantoins - pKa values

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