Three-component domino synthesis of 2-arylquinazoline-4-amines in one pot by activating an sp ~3 C-H bond in a nonmetal catalytic oxidation system

摘要

The nonmetal catalytic oxidation system I _2/tert-butyl hydroperoxide (TBHP) has been unprecedentedly applied to a three-component domino reaction and simultaneously a simple and efficient protocol has been developed to newly synthesize 2-aryl-N-substitutied quinazoline-4-amines in one pot from isatoic anhydride, aromatic amine, and another amine containing methylene adjacent to nitrogen. This protocol is new and practical because both the electron-donating and -withdrawing groups substituted on amines 2 or 3 can survive and provide the corresponding products in reasonable yields. Iodine is essential to the three-component, one-pot reaction unlike the step-wise procedure. The nonmetal catalytic oxidation system I _2/tert-butyl hydroperoxide (TBHP) has been successfully applied to a three-component domino reaction, and a new, simple, efficient protocol has been developed to synthesize 2-aryl-N-substitutied quinazoline-4-amines in one pot from isatoic anhydride, aromatic amine, and another amine containing methylene adjacent to nitrogen.