Synthesis of Acylation Polycyclic Derivatives via Regioselective Acylation/Cyclization of 1,7-Dienes with Acyl Oxime Esters.

A visible-light-induced radical cascade regioselective acylation/cyclization of 1,7-dienes with acyl oxime esters for the preparation of acylation polycyclic compounds via NCR-mediated C-C σ-bond cleavage is established. The transformation involves the cleavage of the C-C σ-bond in acyl oxime esters and selective addition of the electron neutral C═C bonds in 1,7-dienes for the synthesis of acyl polycyclic quinolinone derivatives, not the traditional seven-membered ring products. The strategy offers several advantages, including broad substrate tolerance, no need for bases, hyperstoichiometric radical initiators, and other auxiliaries.

Photocatalytic radical cyclization of N-(o-cyanobiaryl)acrylamides with oxime esters.

A visible-light-mediated radical cascade cyclization of N-(o-cyanobiaryl)acrylamides with oxime esters for the assembly of acyl-containing pyrido[4,3,2-gh]phenanthridines has been developed. The present protocol tolerates a wide range of oxime esters through a single reaction via fragmentation, radical addition, nitrile insertion, and cyclization under mild conditions.