Photo-induced organoselenium-catalyzed synthesis of 2-substituted quinazoline derivatives

Abstract

Herein, a method for the synthesis of 2-substituted quinazoline derivatives from 2-aminobenzylamines and benzylamines using the synergistic action of visible light and organoselenium catalysts was established. Under visible light, the process employs diphenyl diselenide (PhSe)2 as a photocatalyst to achieve the best yield of 97 % in 3 h without the use of other powerful oxidants or selective fluorine excitation, and tolerated a variety of substrates with yields ranging from 60 % to 97 %. Moreover, substitution of benzylamine with benzaldehyde, benzoylformic acid or mandelic acid expanded the substrate scopes for synthesis of 2-substituted quinazolines and quinazolinones. This opens new avenues for further study of the catalytic reaction of organic selenium and promotes the development of green synthetic chemistry.