One‐Step Synthesis of Dicarboxamides through Pd‐Catalysed Aminocarbonylation with Diamines as N‐Nucleophiles
2015
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.
Keywords:
- Correction
- Source
- Cite
- Save
- Machine Reading By IdeaReader
72
References
13
Citations
NaN
KQI