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

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 modera...

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Bibliographic Details
Published in:Organic letters 2019-01, Vol.21 (1), p.320-324
Main Authors: Adouama, Chérif, Budén, María E, Guerra, Walter D, Puiatti, Marcelo, Joseph, Benoît, Barolo, Silvia M, Rossi, Roberto A, Médebielle, Maurice
Format: Article
Language:English
Subjects:
Chemical Sciences
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Summary: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 SNAr).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03831