Divergent Construction of Azaheterocycles via Alkoxyl Radical-Triggered C-C Bond Cleavage/Cyclization of N-Functionalized Acrylamides

An array of redox-neutral alkylation/cyclization cascadereactionsof N-functionalized acrylamides with cycloalkyl hydroperoxideswere achieved via the alkoxyl radical-triggered C-C bond cleavage.Through adjusting the radical acceptors on the N atom,a variety of keto-alkylated chain-containing azaheterocycles, includingindolo[2,1-a]isoquinolin-6(5H)-ones,quinoline-2,4-diones, and pyrido[4,3,2-gh]phenanthridineswere constructed by a one-pot procedure with good yields and excellentfunctional group tolerance.

Automated summary

A series of redox-neutral alkylation/cyclization cascade reactions of N-functionalized acrylamides with cycloalkyl hydroperoxides were achieved through alkoxyl radical-triggered C-C bond cleavage. By adjusting the radical acceptors on the N atom, various keto-alkylated chain-containing azaheterocycles were constructed, including indolo[2,1-a]isoquinolin-6(5H)-ones, quinoline-2,4-diones, and pyrido[4,3,2-gh]phenanthridines, using a one-pot procedure with high yields and excellent functional group tolerance.