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Issue 15, 2019
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Synthesis of 2-substituted indoles through cyclization and demethylation of 2-alkynyldimethylanilines by ethanol

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Abstract

Herein, we demonstrated that 2-alkynyldimethylamines easily cyclize in EtOH according to a 5-endo-dig annulation into 2-substituted indoles without the aid of any additives or any metal catalysts to activate the triple bond. Thus, a variety of functionalized 2-styrylindoles, 2-arylindoles, 2-alkynylindoles, and 2-alkylindoles were prepared in high to excellent yields according to an environmentally friendly protocol. The mechanism has been explored to better understand this eco-friendly access to 2-substituted indoles and DFT calculations rationalized the role of the solvent in this N-annulation/dealkylation process.

Graphical abstract: Synthesis of 2-substituted indoles through cyclization and demethylation of 2-alkynyldimethylanilines by ethanol

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Supplementary files

Article information


Submitted
05 Jun 2019
Accepted
10 Jul 2019
First published
11 Jul 2019

Green Chem., 2019,21, 4204-4210
Article type
Paper

Synthesis of 2-substituted indoles through cyclization and demethylation of 2-alkynyldimethylanilines by ethanol

G. Zhao, C. Roudaut, V. Gandon, M. Alami and O. Provot, Green Chem., 2019, 21, 4204
DOI: 10.1039/C9GC01880H

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