ONE-POT SYNTHESIS OF N,N'-BISACYLIMIDAZOLIDINES - POTENTIAL NEW ACYL ANION EQUIVALENTS

Imidazolidines bearing acyl groups on the nitrogen atoms have been pre pared in a one-pot, two stage process. 1,2-Diamines were condensed wit h a variety of aldehydes and the subsequent N,N'-bisunsubstituted imid azolidines were acylated with a selection of acid chlorides or acid an hydrides. The product N,N'-bisacylimidazolidines were investigated as potential acyl anion equivalents by treatment with a base to deprotona te between the two nitrogen atoms. The carbanion thus formed was quenc hed with a variety of electrophiles. 2-Benzyl-imidazolidine 3k was cle aved to regenerate the carbonyl group, with recovery of the 1,2-diamin e, using trifluoroacetic acid.