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DOI: 10.1055/s-1996-5676
One-Pot Synthesis of N,N’-Bisacylimidazolidines; Potential New Acyl Anion Equivalents
Publication History
Publication Date:
31 December 2000 (online)
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