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

Carrilho, Rui M. B. and Almeida, Ana R. and Kiss, Mercédesz and Kollár, László and Skoda-Földes, Rita and Dabrowski, Janusz M. and Moreno, Maria José S. M. and Pereira, Mariette M. (2015) One-Step Synthesis of Dicarboxamides through Pd-Catalysed Aminocarbonylation with Diamines as N-Nucleophiles. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. pp. 1840-1847. ISSN 1434-193X

Text EurJOrgChem2015.pdf Restricted to Repository staff only Download (1MB) | Request a copy

Abstract

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.

Actions (login required)

Edit Item