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

Abstract

Abstract 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—78% yields, while the corresponding α-phenylthio amide produced 1-phenylthio-3-azabicyclo[3.1.0]hexan-2-one in 74% 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.