Cobalt-catalyzed carbonylative cyclization of N-(2-Vinylphenyl) nicotinamides to access (NH)-quinolin-2(1H)-ones

A cobalt-catalyzed carbonylative cyclization of N-(2-vinylphenyl)picolinamides for the construction of (NH)-quinolin-2(1H)-one scaffolds has been developed. In this reaction, various free (NH)-quinolin-2(1H)-ones were produced in good yields (up to 92%) by employing benzene-1,3,5-triyl triformate (TFBen) as the CO source and picolinamide as the traceless directing group. Moreover, several synthetic transformations of the obtained (NH)-quinolin-2(1H)-ones were performed and a facile and rapid access to the core skeleton of Tipifarnib was realized to demonstrate the utility of this protocol.

Automated summary

A cobalt-catalyzed carbonylative cyclization using N-(2-vinylphenyl)picolinamides has been developed for the construction of (NH)-quinolin-2(1H)-one scaffolds. By employing benzene-1,3,5-triyl triformate as the CO source and picolinamide as the traceless directing group, various (NH)-quinolin-2(1H)-ones were obtained in good yields (up to 92%). Additionally, the obtained (NH)-quinolin-2(1H)-ones were subjected to several synthetic transformations, demonstrating the utility of this protocol for the rapid access to the core skeleton of Tipifarnib.