Diastereoselective synthesis of novel N-substituted pyrrolidine-2-one containing piperazine derivatives

Synthesis of novel hybrid derivatives of two known scaffolds, pyrrolidine-2-one and piperazine, is described. Initially, the Ugi reaction of phenylglyoxal, aromatic amines, coumarin-3-carboxylic acid and isocyanides in methanol resulted in the formation of dihydrochromeno[3,4-c]pyrrole-3,4-diones. The obtained products were then treated with N-alkylpiperazines in dichloromethane to afford the novel N-substituted pyrrolidine-2-one containing piperazine derivatives in satisfactory yields. The proof of the structures was carried out by means of spectroscopic information and X-ray crystallography.