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. Issue 6 (2nd January 2018)

• Record Type: Journal Article
• Authors: Wang, Bingbing; Jin, Shengnan; Sun, Song; Cheng, Jiang
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 6(2018)
• Page Start: 958
• Page End: 961
• Publication Date: 2018-01-02
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo01048f
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A di- tert -butyl peroxide-promoted radical rearrangement of N -sulfonyl- N -aryl propynamides has been developed, giving 2-sulfonyl-3-aryl-2(1 H )-quinolinones in moderate to good yields. 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(1 H )-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.