Issue 8, 2016

Synthesis of oxindoles via reductive CO2 fixation

Abstract

The synthesis of 3-aryl-3-hydroxy-2-oxindoles, which are a structural motif found in various natural products and pharmaceutically active compounds, was conducted via reductive coupling of (2-aminophenyl)(aryl)methanone derivatives and CO2 as a key step. The conditions employing Mg with chlorotrimethylsilane in DMA are the best for the reductive coupling, where the aryl halide moiety is intact. This reaction proceeds well without the protection of the amino group. The reductive coupling and acid-catalyzed lactam formation can be performed in a one-pot reaction to give the oxindoles.

Graphical abstract: Synthesis of oxindoles via reductive CO2 fixation

Supplementary files

Article information

Article type
Research Article
Submitted
17 mar. 2016
Accepted
14 jun. 2016
First published
29 jun. 2016
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2016,3, 929-933

Synthesis of oxindoles via reductive CO2 fixation

T. Amaya, I. Kurata and T. Hirao, Org. Chem. Front., 2016, 3, 929 DOI: 10.1039/C6QO00107F

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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