Synthesis and Geometric and Electronic Structure of 5-Aryl-4-arylcarbonyl-3-hydroxy-2,5-dihydropyrrol-2-ones and Their Reactions with Arylamines

摘要

Methyl (arylcarbonyl)pyruvates were reacted with aromatic aldehydes and amonium acetate to prepare 5-aryl-4-arylcarbonyl-2,5-dihydropyrrol-2-ones whose reaction with aromatic amines gave 5-aryl-3-arylamino-4-arylcarbonyl-2,5-dihydropyrrol-2-ones.MNDO-PM3 semiempirical calculations of 4-benzoyl-3-hydroxy-5-phenyl-2,5-dihydropyrrol-2-one and the zwitter-ionic intermediate formed by aniline addition were performed to explain the experimental data obtained.