Regioselective Reversal Cyclization To Access either Eight-Membered Sulfur-Containing Heterocycle-Fused γ-Pyrones or 2-(1,4-Dithianyl)-4-pyrones from the Same Precursors.,The Journal of Organic Chemistry

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Regioselective Reversal Cyclization To Access either Eight-Membered Sulfur-Containing Heterocycle-Fused γ-Pyrones or 2-(1,4-Dithianyl)-4-pyrones from the Same Precursors.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-22 , DOI: 10.1021/acs.joc.9b03303
Ling Tang _{1,

2} , Qin Yang _{1,

2} , Jianfang Zhang _{1,

2} , Guisheng Deng _{1,

2}

Affiliation

A regioselective reverse strategy for the construction of eight-membered sulfur-containing heterocycle-fused γ-pyrones and 2-(1,4-dithianyl)-4-pyrones starting from 2-diazo-γ-pyrones and dithioacetals was achieved for the first time. The process combines C-S bond formation via sulfur ylides and C-C bond formation via electron transfer to afford the target molecules in a facile manner with 100% regioselectivity and in excellent isolated yields (up to 90%).

中文翻译：

区域选择性反向环化可从相同的前体中获得八元含硫杂环杂环γ-吡喃酮或2-（1,4-二噻吩基）-4-吡喃酮。

第一个实现了从2-重氮-γ-吡喃酮和二硫缩醛开始构建八元含硫杂环稠合的γ-吡喃酮和2-（1,4-二硫烷基）-4-吡喃酮的区域选择性逆向策略。时间。该方法结合了通过硫酰化物形成的CS键和通过电子转移形成的CC键，以简便的方式提供目标分子，具有100％的区域选择性和极佳的分离产率（最高90％）。

更新日期：2020-01-23

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