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Synthesis 2021; 53(07): 1271-1284
DOI: 10.1055/s-0040-1706542
DOI: 10.1055/s-0040-1706542
paper
Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines
We thank the Université de Rennes 1 and the Centre National de la Recherche Scientifique (F.M.). We acknowledge the European Regional Development Fund (Fonds Européen de Développement Régional, FEDER; D8 VENTURE Bruker AXS diffractometer). L.P. and V.T. thank La Ligue contre le Cancer (French Cancer League; Comité 17 and Comité 86) for financial support and the Cancéropôle Grand Ouest (axis: Marine Molecules, Metabolism and Cancer 3MC) for scientific support. This research has been partly performed as part of the CNRS PICS project ‘Bimetallic synergy for the functionalization of heteroaromatics’.
Abstract
N-Arylation of various 2-acylated anilines with different electron-rich heteroaryl iodides (2- and 3-iodothiophenes, 2- and 3-iodobenzothiophenes, 2-iodobenzofuran) was achieved by using activated copper and potassium carbonate in dibutyl ether at reflux. The reactivity of the different heteroaryl iodides and anilines employed was discussed and rationalized on the basis of their electronic features. Subsequent cyclization by aromatic electrophilic substitution easily took place in the case of C2-free (benzo)thienyl or C3-free (benzo)furyl derivatives, affording original tri- and tetracycles. The antiproliferative activity of most of them was evaluated in A2058 melanoma cells and revealed four chlorinated tetracycles as effective growth inhibitors.
Key words
-
aniline -
thiophene -
iodine -
N-arylation -
copper -
antiproliferative activity -
melanoma cells
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706542.
- Supporting Information
- CIF File
Publikationsverlauf
Eingereicht: 12. August 2020
Angenommen nach Revision: 18. September 2020
Artikel online veröffentlicht:
26. Oktober 2020
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