Download PDF
Synlett 1996; 1996(11): 1109-1111
DOI: 10.1055/s-1996-5676
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >