Synthesis of 3-oxo-4-benzoyl-1-phenylsuccinimide and its reactions with 1,2- dinucleophiles

The base-catalyzed reaction of ethyl benzoylpyruvate (1) with phenyl isocyanate yields the 3-oxo-4-benzoyl-1-phenylsuccinimide (2). Reactions of compound 2 with hydrazine and phenylhydrazine afforded the corresponding pyridazine-3,6-dione derivatives 3a,b. The 3-oxo-4-benzoyl-1-phenylsuccinimide (2) reacts with 1-aminoguanidine, semicarbazide and thiosemicarbazide to form the corresponding N-phenyl maleimide derivatives 4a-c, respectively. The analytical data of these compounds - IR, 1H, and 13C NMR spectral data are reported.