Synthesis of Diversely Substituted Indoloquinolinones via Pd(II)/Cu(II)-Mediated Oxidative C–C Bond Formation and I(III)-Mediated C–N Bond Formation

A series of indoloquinolinones bearing different aromatic substitutents were readily synthesized starting from an aryl amine, a methyl 3-oxo-3-phenylpropanoate derivative, and methoxylamine through a series of reactions of coupling/enamination, oxidative annulation, a one-pot sequence of N-alkylation, saponification and methoxyamidation, and final intramolecular oxidative C–N bond formation. The underpinning of the strategy entails Pd­(OAc)₂/Cu­(OAc)₂-mediated oxidative C­(sp²)–C­(sp²) bond formation and I­(III)-mediated oxidative C­(sp²)–N bond formation.