Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 4, Pages 2395-2401Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02943
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An efficient synthesis of quinazolines based on an iron-catalyzed C(sp(3))-H oxidation and intramolecular C-N bond formation using tent-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(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.
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