Room-Temperature and Transition-Metal-Free Intramolecular α-Arylation of Ketones: A Mild Access to Tetracyclic Indoles and 7-Azaindoles.


Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
04 01 2019
Historique:
pubmed: 24 12 2018
medline: 24 12 2018
entrez: 22 12 2018
Statut: ppublish

Résumé

A novel approach for the synthesis of tetracyclic indoles and 7-azaindoles is reported. The strategy involves four steps, with a fast rt intramolecular α-arylation of ketones as key step. The reaction was inspected synthetically to achieve the synthesis of 11 novel tetracyclic structures with moderate to very good yields (39-85%). Theoretical combined with experimental studies led us to propose a probable polar mechanism (concerted S

Identifiants

pubmed: 30576154
doi: 10.1021/acs.orglett.8b03831
doi:

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Pagination

320-324

Auteurs

Chérif Adouama (C)

Univ Lyon, Université Lyon 1 , CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, 1 rue Victor Grignard , 69622 Villeurbanne Cedex , France.

María E Budén (ME)

INFIQC, Facultad de Ciencias Químicas , Universidad Nacional de Córdoba , X5000HUA Córdoba , Argentina.

Walter D Guerra (WD)

INFIQC, Facultad de Ciencias Químicas , Universidad Nacional de Córdoba , X5000HUA Córdoba , Argentina.

Marcelo Puiatti (M)

INFIQC, Facultad de Ciencias Químicas , Universidad Nacional de Córdoba , X5000HUA Córdoba , Argentina.

Benoît Joseph (B)

Univ Lyon, Université Lyon 1 , CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, 1 rue Victor Grignard , 69622 Villeurbanne Cedex , France.

Silvia M Barolo (SM)

INFIQC, Facultad de Ciencias Químicas , Universidad Nacional de Córdoba , X5000HUA Córdoba , Argentina.

Roberto A Rossi (RA)

INFIQC, Facultad de Ciencias Químicas , Universidad Nacional de Córdoba , X5000HUA Córdoba , Argentina.

Maurice Médebielle (M)

Univ Lyon, Université Lyon 1 , CNRS, INSA, CPE-Lyon, ICBMS, UMR 5246, 1 rue Victor Grignard , 69622 Villeurbanne Cedex , France.

Classifications MeSH