Copper-Catalyzed Coupling between ortho-Haloanilines and Lactams/Amides: Synthesis of Benzimidazoles and Telmisartan
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 con...
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Published in | Journal of organic chemistry Vol. 89; no. 8; pp. 5469 - 5479 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
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American Chemical Society
19.04.2024
Amer Chemical Soc |
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Abstract | 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. |
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AbstractList | 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. 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 -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. |
Author | Boquet, Vincent Beltran, Raphaël Ferey, Vincent Hansjacob, Pierre Evano, Gwilherm Sauber, Chris Rodier, Fabien Theunissen, Cédric |
AuthorAffiliation | Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques WEL Research Institute Sanofi, Route d’Avignon |
AuthorAffiliation_xml | – name: Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques – name: WEL Research Institute – name: Sanofi, Route d’Avignon |
Author_xml | – sequence: 1 givenname: Vincent surname: Boquet fullname: Boquet, Vincent organization: Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques – sequence: 2 givenname: Chris surname: Sauber fullname: Sauber, Chris organization: Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques – sequence: 3 givenname: Raphaël surname: Beltran fullname: Beltran, Raphaël – sequence: 4 givenname: Vincent surname: Ferey fullname: Ferey, Vincent organization: Sanofi, Route d’Avignon – sequence: 5 givenname: Fabien surname: Rodier fullname: Rodier, Fabien – sequence: 6 givenname: Pierre surname: Hansjacob fullname: Hansjacob, Pierre organization: Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques – sequence: 7 givenname: Cédric orcidid: 0000-0001-9567-7847 surname: Theunissen fullname: Theunissen, Cédric organization: Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques – sequence: 8 givenname: Gwilherm orcidid: 0000-0002-2939-4766 surname: Evano fullname: Evano, Gwilherm email: Gwilherm.Evano@ulb.be organization: WEL Research Institute |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38565075$$D View this record in MEDLINE/PubMed |
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Keywords | CASCADE REACTIONS AMINES ONE-POT N BOND FORMATION LIGAND 1,2-DISUBSTITUTED BENZIMIDAZOLES EFFICIENT DERIVATIVES CYCLIZATION O-HALOANILINES |
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Snippet | An efficient copper-catalyzed synthesis of (annelated) benzimidazoles is reported. This transformation is based on a simple and straightforward one-pot... |
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Title | Copper-Catalyzed Coupling between ortho-Haloanilines and Lactams/Amides: Synthesis of Benzimidazoles and Telmisartan |
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