Nucleophilic addition of amines to N-aryl-substituted pyrrolin-2-ones

The nucleophilic addition of n-butyl- and benzylamines to 1-(4-nitrophenyl)-5H-pyrrolin-5-one and 1-(4-sulfamoylphenyl)-5H-pyrrolin-2-one at 50°C in an excess of the amines with the formation of N-substituted amides of 3-alkyl(benzyl)amino-4-(4-R-anilino)butyric acids was investigated. The N-substituted amides of 3-arylamino-4-hydroxybutyric and 4-hydroxy-2-butenoic acids were synthesized from 2(5H)-furanone and aromatic amines (1:3) at 180°C. 4-Alkylamino-1-(4-nitrophenyl)pyrrolid-2-ones were obtained in the reaction of 1-(4-nitrophenyl)-5-pyrrolin-2-one with ammonia or aliphatic, alicyclic, and aromatic amines (1:3, 90°C, in DMF).