Issue 6, 2018

Radical rearrangement of N-sulfonyl-N-aryl propynamides: proceeding with homolytic N–SO2 bond cleavage and 6-endo-dig cyclization toward 3-sulfonyl-2(1H)-quinolinones

Abstract

A di-tert-butyl peroxide-promoted radical rearrangement of N-sulfonyl-N-aryl propynamides has been developed. This procedure proceeds with sequential homolytic N–SO2 bond cleavage and 6-endo-dig radical cyclization to access a variety of 2-sulfonyl-3-aryl-2(1H)-quinolinones with high atom economy. The cross experiment confirmed the involvement of an intermolecular rearrangement, which was triggered by the thermo-induced homolytic cleavage of the N–SO2 bond.

Graphical abstract: Radical rearrangement of N-sulfonyl-N-aryl propynamides: proceeding with homolytic N–SO2 bond cleavage and 6-endo-dig cyclization toward 3-sulfonyl-2(1H)-quinolinones

Supplementary files

Article information

Article type
Research Article
Submitted
23 נוב 2017
Accepted
16 דצמ 2017
First published
18 דצמ 2017

Org. Chem. Front., 2018,5, 958-961

Radical rearrangement of N-sulfonyl-N-aryl propynamides: proceeding with homolytic N–SO2 bond cleavage and 6-endo-dig cyclization toward 3-sulfonyl-2(1H)-quinolinones

B. Wang, S. Jin, S. Sun and J. Cheng, Org. Chem. Front., 2018, 5, 958 DOI: 10.1039/C7QO01048F

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