Pd-catalyzed regioselective cycloaminocarbonylation of aminonaphthoquinones: synthesis and biological evaluation of benzo[g]quinolinetriones.

A new family of 3,4-dihydrobenzo[g]quinoline-2,5,10(1H)-triones was synthesized via palladium-catalyzed regioselective cycloaminocarbonylation of 2-allyl-3-amino-1,4-naphthoquinone derivatives. Regioselectivity was directed toward the formation of six-membered ring lactams using a PdCl2/Xantphos catalytic system under syngas conditions. The resulting lactams fused to the naphthalene-1,4-dione framework were obtained with high regioselectivity and moderate isolated yields. The new compounds exhibited significant anticancer activity along with potent antioxidant effects against lipid peroxidation.