One-Step Synthesis of Dicarboxamides through Pd-Catalysed Aminocarbonylation with Diamines as N-Nucleophiles

An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed amino carbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended signifi cantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70 %) being achieved with 1-iodocyclohexene as substrate and 1,4-di aminobutane as nucleophile, at 100 °C and 30 bar of CO. When iodobenzene was used as model aryl halide, the high est yield of the target dibenzamides (ca. 65 %) was obtained with 1,4-diaminobenzene as coupling amine, at 100 °C and 10 bar of CO. Preliminary studies on their in vitro cytotoxicity against human lung carcinoma A549 cells showed N,N�- (butane-1,4-diyl)dibenzamide and androst-16-ene-based di carboxamides to be the most efficient cytotoxic agents, with IC50values of approximately 40μM.