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(sp(2))-C(sp(2)) bond formation and I(III)-mediated oxidative C(sp(2))-N bond formation.