One-step synthesis of dicarboxamides through Pd-catalysed aminocarbonylation with diamines as N-nucleophiles

Rui M.B. Carrilho, Ana R. Almeida, Mercédesz Kiss, László Kollár, Rita Skoda-Földes, Janusz M. Dąbrowski, Maria José S.M. Moreno, Mariette M. Pereira

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly 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-diaminobutane as nucleophile, at 100°C and 30 bar of CO. When iodobenzene was used as model aryl halide, the highest 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 dicarboxamides to be the most efficient cytotoxic agents, with IC50 values of approximately 40 μM.

Original languageEnglish
Pages (from-to)1840-1847
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number8
DOIs
Publication statusPublished - Mar 1 2015

Keywords

  • Antitumor agents
  • Carbonylation
  • Dicarboxamides
  • Medicinal chemistry
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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