Brief introduction of (1R,2R)-Cyclohexane-1,2-diamine

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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 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 100C 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 100C 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 muM.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI