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■ On the Synthesis of Unsaturated 4(5H)-Imidazolones

Carlos Cativiela, Javier Chueca, José I. García, and Enrique Meléndez*

*Department of Chemistry, University of Zaragoza, 50009-Zaragoza, Spain

Abstract

(Z)-2,3-Diphenyl-5-benzylidene-4(5H)-imidazolone and (Z)-2,3-diphenyl-5-(α-phenylethylidene)-4(5H)-imidazolone were obtained from the corresponding (Z)-2-phenyl-4-benzylidene-5(4H)-oxazolone and (Z)-2-phenyl-4-(α-phenylethylidene)-5(4H)-oxazolone and aniline. (2)-2,3-Diphenyl-5-benzylidene-4(5H)-imidazolone reacted with diazomethane to afford a mixture of stereoisomeric spirocyclopropanes and (Z)-2,3-diphenyl-5-(α-phenylethylidene)-4(5H)-imidazolone, the product ratios being modified with the appropriate solvent. Anilide of 1-phenyl-4-methyl-3-isoquinolincarboxylic acid or (Z)-2,3-diphenyl-5-(α-phenylethylidene)-4(5H)-imidazolone were obtained from anilide of (Z)-2-benzamidocinnamic acid depending upon the reaction conditions.