Issue 3, 2017

Zinc-catalyzed chemoselective alkylation of α-keto amides with 2-alkylazaarenes

Abstract

A zinc-catalyzed C(sp3)–H addition of 2-alkylazaarenes to α-keto amides to furnish azaarene incorporated α-hydroxy amides has been developed with a wide range of substrates in moderate to excellent yields, respectively. Chemoselective alkylation of the keto functionality of the α-keto amides in the presence of simple ketones is the key advantage of this Zn-catalyzed transformation. This approach has been demonstrated to one gram-scale synthesis. 1H NMR and D2O exchange experimental studies reveal that the reaction proceeds through a Zn-enamide intermediate.

Graphical abstract: Zinc-catalyzed chemoselective alkylation of α-keto amides with 2-alkylazaarenes

Supplementary files

Article information

Article type
Paper
Submitted
08 Nov 2016
Accepted
12 Dec 2016
First published
12 Dec 2016

Org. Biomol. Chem., 2017,15, 691-700

Zinc-catalyzed chemoselective alkylation of α-keto amides with 2-alkylazaarenes

A. Muthukumar and G. Sekar, Org. Biomol. Chem., 2017, 15, 691 DOI: 10.1039/C6OB02432G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements