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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

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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

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Publication details

The article was received on 23 Nov 2017, accepted on 16 Dec 2017 and first published on 18 Dec 2017


Article type: Research Article
DOI: 10.1039/C7QO01048F
Citation: Org. Chem. Front., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C7QO01048F

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