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.