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Issue 16, 2019

Zn(OTf)2-catalyzed access to symmetrical and unsymmetrical bisindoles from α-keto amides

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Abstract

Zn(OTf)2-catalyzed synthesis of 3,3′-bisindolyl acetamides from α-keto amides is developed. Both aromatic α-keto amides substituted with electron-donating as well as -withdrawing groups and aliphatic α-keto amides are well tolerated to provide symmetrical bisindoles in moderate to excellent yields. The chemoselective bisindolylation of the keto group of α-keto amides in the presence of a simple keto functionality is successfully achieved in good yields. The transformation is further extended to the synthesis of challenging unsymmetrical bisindoles by treating indolyl α-hydroxy amides with substituted indoles. The unsymmetrical bisindoles are isolated in good to excellent yields.

Graphical abstract: Zn(OTf)2-catalyzed access to symmetrical and unsymmetrical bisindoles from α-keto amides

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Article information


Submitted
16 Jan 2019
Accepted
27 Mar 2019
First published
01 Apr 2019

Org. Biomol. Chem., 2019,17, 3921-3933
Article type
Paper

Zn(OTf)2-catalyzed access to symmetrical and unsymmetrical bisindoles from α-keto amides

A. Muthukumar, G. N. Rao and G. Sekar, Org. Biomol. Chem., 2019, 17, 3921 DOI: 10.1039/C9OB00114J

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