Issue 7, 2022

An amine template strategy to construct successive C–C bonds: synthesis of benzo[h]quinolines by a deaminative ring contraction cascade

Abstract

We developed a convergent strategy to build, cyclize and excise nitrogen from tertiary amines for the synthesis of polyheterocyclic aromatics. Biaryl-linked azepine intermediates can undergo a deaminative ring contraction cascade reaction, excising nitrogen with the formation of an aromatic core. This strategy and deaminative ring contraction reaction are useful for the synthesis of benzo[h]quinolines.

Graphical abstract: An amine template strategy to construct successive C–C bonds: synthesis of benzo[h]quinolines by a deaminative ring contraction cascade

Supplementary files

Article information

Article type
Communication
Submitted
17 Nov 2021
Accepted
18 Jan 2022
First published
27 Jan 2022

Org. Biomol. Chem., 2022,20, 1379-1385

An amine template strategy to construct successive C–C bonds: synthesis of benzo[h]quinolines by a deaminative ring contraction cascade

T. P. McFadden, C. I. Nwachukwu and A. G. Roberts, Org. Biomol. Chem., 2022, 20, 1379 DOI: 10.1039/D1OB02245H

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