Metal-free oxidative functionalization of a C(sp(3))-H bond adjacent to nitrogen and intramolecular aromatic cyclization for the preparation of 6-amidophenanthridines

J Org Chem. 2015 Mar 20;80(6):3151-8. doi: 10.1021/acs.joc.5b00058. Epub 2015 Mar 11.

Abstract

A metal-free cyclization reaction of 2-isocyanobiphenyls with amide derivatives by using tert-butyl peroxybenzoate (TBPB) as oxidant was developed, which provided an access to pharmacologically interesting 6-amidophenanthridine compounds. The reactions proceeded through a sequence of functionalization of the C(sp(3))-H bond adjacent to the nitrogen atom and intramolecular radical aromatic cyclization with good chemistry yields.