Copper-Catalyzed Coupling between ortho -Haloanilines and Lactams/Amides: Synthesis of Benzimidazoles and Telmisartan.

Autor: Boquet V; Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium., Sauber C; Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium., Beltran R; Sanofi, 45 Chemin de Météline, 04200 Sisteron, France., Ferey V; Sanofi, Route d'Avignon, 30390 Aramon, France., Rodier F; Sanofi, 45 Chemin de Météline, 04200 Sisteron, France., Hansjacob P; Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium., Theunissen C; Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium., Evano G; Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium.; WEL Research Institute, Avenue Pasteur 6, 1300 Wavre, Belgium.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Apr 19; Vol. 89 (8), pp. 5469-5479. Date of Electronic Publication: 2024 Apr 02.
DOI: 10.1021/acs.joc.3c02905
Abstrakt: An efficient copper-catalyzed synthesis of (annelated) benzimidazoles is reported. This transformation is based on a simple and straightforward one-pot sequence involving a copper-catalyzed cross coupling between o -haloanilines and lactams/amides followed by a subsequent cyclization under acidic conditions. A variety of (annelated) benzimidazoles could be easily obtained in high yields from readily available starting materials, and this procedure could be further applied to the synthesis of the antihypertensive blockbuster drug telmisartan.
Databáze: MEDLINE
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