Synthesis of Annulated γ-Lactams via Intramolecular 1,3-Dipolar Cycloadditions of Functionalized N-Allyl α-Diazo Amides

Article abstract of DOI:10.1246/bcsj.66.1496

N-Allyldiazoacetamides containing a phosphinyl group at the α-position underwent the intramolecular 1, 3-cycloaddition, followed by 1,3-hydrogen shift to afford 6a-diethoxyphosphinyl-3a,4,5,6a-tetrahydropyrrolo<3,4-c>pyrazol-6(1H)-ones in 74-78percent yields, while the corresponding α-phenylthio amide produced 1-phenylthio-3-azabicyclo<3.1.0>hexan-2-one in 74percent yield via extrusion of N2 from the intramolecular 1,3-cycloadduct.In the application of these compounds to the conversion of functionality, the former gave a fused tricyclic heterocycle and the latter gave deallylated compounds.