Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines

Salima Bouarfa; Ghenia Bentabed-Ababsa; William Erb; Laurent Picot; Valérie Thiéry; Thierry Roisnel; Vincent Dorcet; Florence Mongin

doi:10.1055/s-0040-1706542

Synthesis, Table of Contents

Synthesis 2021; 53(07): 1271-1284
DOI: 10.1055/s-0040-1706542

paper

Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines

Salima Bouarfa

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France

^bLaboratoire de Synthèse Organique Appliquée, Faculté des Sciences Exactes et Appliquées, Université d’Oran 1 Ahmed Ben Bella, BP 1524 El M’Naouer, 31000 Oran, Algeria Email: bentabedg@gmail.com

,

Ghenia Bentabed-Ababsa∗

^bLaboratoire de Synthèse Organique Appliquée, Faculté des Sciences Exactes et Appliquées, Université d’Oran 1 Ahmed Ben Bella, BP 1524 El M’Naouer, 31000 Oran, Algeria Email: bentabedg@gmail.com

,

William Erb

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France

,

Laurent Picot∗

^cLa Rochelle Université, Laboratoire Littoral Environnement et Sociétés, UMRi CNRS 7266, Université de La Rochelle, 17042 La Rochelle, France Email: laurent.picot@univ-lr.fr

,

Valérie Thiéry

^cLa Rochelle Université, Laboratoire Littoral Environnement et Sociétés, UMRi CNRS 7266, Université de La Rochelle, 17042 La Rochelle, France Email: laurent.picot@univ-lr.fr

,

Thierry Roisnel

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France

,

Vincent Dorcet

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France

,

Florence Mongin ∗

^aUniv Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France

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Abstract

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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

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References

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