One-Pot Synthesis of N,N’-Bisacylimidazolidines; Potential New Acyl Anion Equivalents

Iain Coldham; Philippe M. A. Houdayer; Robert A. Judkins; David R. Witty

doi:10.1055/s-1996-5676

Synlett 1996; 1996(11): 1109-1111
DOI: 10.1055/s-1996-5676

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One-Pot Synthesis of N,N’-Bisacylimidazolidines; Potential New Acyl Anion Equivalents

Iain Coldham^* , Philippe M. A. Houdayer, Robert A. Judkins, David R. Witty

^*Department of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, U.K., Fax 01392 263434, E-Mail I.Coldham@exeter.ac.uk

Abstract

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Imidazolidines bearing acyl groups on the nitrogen atoms have been prepared in a one-pot, two stage process. 1,2-Diamines were condensed with a variety of aldehydes and the subsequent N,N’-bisunsubstituted imidazolidines were acylated with a selection of acid chlorides or acid anhydrides. The product N,N’-bisacylimidazolidines were investigated as potential acyl anion equivalents by treatment with a base to deprotonate between the two nitrogen atoms. The carbanion thus formed was quenched with a variety of electrophiles. 2-Benzyl-imidazolidine 3k was cleaved to regenerate the carbonyl group, with recovery of the 1,2-diamine, using trifluoroacetic acid.

1,2-diamine - imidazolidine - acyl anion equivalent - deprotonation

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