An I-promoted, metal-free protocol has been developed for the one-pot synthesis of 6-aroyl-5,6-dihydro-8-quinazolino[4,3-]quinazolin-8-ones from readily accessible substrates. This reaction involves the sp C-H oxidation of aryl methyl ketones to phenylglyoxal, followed by imine formation and intramolecular nucleophilic addition, resulting in the formation of two new C-N bonds. Furthermore, the method is applicable to a wide range of aryl methyl ketones, including heterocycles and drug-derived substrates, yielding the desired products with yields ranging from 62% to 93%. Additionally, the practical utility of this approach was demonstrated through gram-scale synthesis.
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