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 ⵏⵓⵡ 2017
Accepted
16 ⴷⵓⵊ 2017
First published
18 ⴷⵓⵊ 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

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