Novel synthesis of N-alkyl-3,4-disubstituted pyrrolidine-2,5-diones: Condensation of α-oxoketene O,N-acetals and maleic anhydride

A novel method for the synthesis of N-alkyl-3-acyl-4-alkoxycarbonylmethylpyrrolidine-2,5-diones (3) was accomplished. α-Oxoketene O,N-acetals (1) reacted with maleic anhydride (2) at 80–110 °C for 5 h without solvent to give 3 in moderate to good yield (36–74%). Single X-ray crystallographic analysis showed that the two substituents on C-3 and C-4 were trans.