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

An efficient synthesis of quinazolines based on an iron-catalyzed C­(sp³)-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 FeCl₂-catalyzed C­(sp³)-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.