Synthesis of Quinazolines via an Iron-Catalyzed Oxidative Amination of N–H Ketimines

An efficient synthesis of quinazolines based on an iron-catalyzed C(sp 3 )-H oxidation and intramolecular C–N bond formation using tert -BuOOH as the terminal oxidant is described. The reaction of readily available 2-alkylamino benzonitriles with various organometallic reagents led to 2-alkylamino N–H ketimine species. The FeCl 2 -catalyzed C(sp 3 )-H oxidation of the alkyl group employing tert -BuOOH followed by intramolecular C–N bond formation and aromatization afforded a wide variety of 2,4-disubstituted quinazolines in good to excellent yields.