Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines - La Rochelle Université Accéder directement au contenu
Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2021

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

Résumé

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.
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Dates et versions

hal-03035983 , version 1 (28-06-2022)

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Salima Bouarfa, Ghenia Bentabed-Ababsa, William Erb, Laurent Picot, Valérie Thiéry, et al.. Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines. Synthesis: Journal of Synthetic Organic Chemistry, 2021, 53 (07), pp.1271-1284. ⟨10.1055/s-0040-1706542⟩. ⟨hal-03035983⟩
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