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One‐Step Synthesis of Dicarboxamides through Pd‐Catalysed Aminocarbonylation with Diamines as N‐Nucleophiles
Author(s) -
Carrilho Rui M. B.,
Almeida Ana R.,
Kiss Mercédesz,
Kollár László,
SkodaFöldes Rita,
Dąbrowski Janusz M.,
Moreno Maria José S. M.,
Pereira Mariette M.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403444
Subject(s) - chemistry , nucleophile , iodobenzene , substrate (aquarium) , amination , amine gas treating , yield (engineering) , medicinal chemistry , aryl , palladium , alkyl , alcohol , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , oceanography , materials science , metallurgy , geology
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 IC 50 values of approximately 40 μ M .