FIVE-MEMBERED 2,3-DIOXOHETEROCYCLES 15. SYNTHESIS AND -SIGMATROPIC REARRANGEMENT OF 1,5-DIARYL-3-DIPHENYLMETHOXY-4-ETHOXYCARBONYL-2,5-DIHYDROPYRROL-2-ONES

Article abstract of DOI:10.1007/BF00756412

Ethyl oxaloacetate reacts with a mixture of an aromatic aldehyde and an arylamine to give 1,5-diaryl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones, which react with diphenyldiazomethane to give the O-alkylation products.On heating, the latter undergo suprafacial <1,3>-sigmatropic rearrangement to 1,5-diaryl-4-diphenylmethyl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones.The effects of the type of migrating group on the rearrangement are discussed.