A new method for generation and intramolecular diels-alder reaction of N-acyl and N-alkoxycarbonyl-1-aza-1,3-butadibnes. A one-pot synthesis of 1,7,8,8a-tetrahydro-3(2H)-indolizinones and 1,2,3,8,9,9a-hexahydro-4(4h)-quinolinones from α,β-unsaturated aldehydes

Article abstract of DOI:10.1016/S0040-4039(00)97462-8

A one-pot transformation, made up of i) generation of N-trimethylsilylaldimines from α,β-unsaturated aldehyde, ii) exchange of the silyl group by acyl and oxycarbonyl groups, and iii) intramolecular Diels-Alder reaction of the resulting ψ′,ω′-unsaturated N-acyl-and a related N-oxycarbonyl-1-aza-1-3-butadienes in boiling xylene, gave 1,7,8,8a-tetrahydro-3(2H)-indolizinones (5), the 2-oxa derivatives of 5, and 1,2,3,8,9,9a-hexahydro-4(4H)-quinolizinones in practical yields.