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†,Organic Chemistry Frontiers

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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†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-12-18 00:00:00 , DOI: 10.1039/c7qo01048f
Bingbing Wang _{1,

2,

3,

4,

5} , Shengnan Jin _{1,

2,

3,

4,

5} , Song Sun _{1,

2,

3,

4,

5} , Jiang Cheng _{1,

2,

3,

4,

5}

Affiliation

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.

中文翻译：

N-磺酰基-N-芳基丙酰胺的 自由基重排：进行均相的N–SO ₂键裂解和6-内挖式环化，形成3-磺酰基-2（1 H）-喹啉酮†

的二-叔丁基过氧化物促进的自由基重排Ñ -sulfonyl- ñ -芳基propynamides已经研制成功。此过程依次进行均相N–SO ₂键裂解和6-内挖基自由基环化，以得到具有高原子经济性的各种2-磺酰基-3-芳基-2（1 H）-喹啉酮。交叉实验证实了分子间重排的参与，这是由热诱导的N–SO ₂键的均质裂解引起的。

更新日期：2017-12-18

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