Synthesis of 2-aryl quinazolinones via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds.

ABSTRACT

Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95%. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles.