CuO nanoparticle catalyzed synthesis of 2,3-disubstituted quinazolinones via sequential N-arylation and oxidative C–H amidation

Abstract

CuO nanoparticle catalyzed synthesis of 2,3-disubstituted quinazolinones has been accomplished from 2-halobenzamides and (aryl)methanamines under an air atmosphere. This synthesis of the N-heterocycle involves a sequential Ullmann coupling [between 2-halobenzamide and (aryl)methanamine], oxidation of the in situ generated secondary amine to imine. This is then followed by an intramolecular nucleophilic attack of the amidic N–H on to the imine carbon (C–N bond formation) resulting in the synthesis of 2,3-disubstituted quinazolinones. The recyclability of the catalyst and tolerance of a wide range of functional groups makes this method efficient and cost-effective.