Synthesis of 3-(((2,3-dihydrobenzofuran-3-yl)methyl)sulfonyl) coumarins through the reaction of 2-(allyloxy)anilines, sulfur dioxide, and aryl propiolates,Organic Chemistry Frontiers

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Synthesis of 3-(((2,3-dihydrobenzofuran-3-yl)methyl)sulfonyl) coumarins through the reaction of 2-(allyloxy)anilines, sulfur dioxide, and aryl propiolates
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-09-05 00:00:00 , DOI: 10.1039/c7qo00787f
Xuefeng Wang _{1,

2,

3,

4,

5} , Tong Liu _{4,

5,

6,

7} , Danqing Zheng _{4,

5,

6,

7} , Qian Zhong _{1,

2,

3,

4} , Jie Wu _{4,

5,

6,

7,

8}

Affiliation

A facile route to 3-((2,3-dihydrobenzofuran-3-yl)methyl)sulfonyl coumarins through the reaction of 2-(allyloxy)anilines, DABCO-bis(sulfur dioxide), and aryl propiolates is achieved. During the reaction process, a 2-(allyloxy)aryl radical would be generated in situ, which would undergo the intramolecular addition of a double bond to afford an alkyl radical intermediate. Further insertion of sulfur dioxide would produce an alkylsulfonyl radical. The subsequent combination with aryl propiolates would provide sulfonyl-bridged dihydrobenzofuran and coumarin derivatives through radical cyclization and rearrangement.

中文翻译：

通过2-（烯丙氧基）苯胺，二氧化硫和丙酸芳基酯的反应合成3-（（（（2,3-二氢苯并呋喃-3-基）甲基）磺酰基）香豆素

通过2-（烯丙氧基）苯胺，DABCO-双（二氧化硫）和丙酸芳基酯的反应，获得了3-（（2,3-二氢苯并呋喃-3-基）甲基）磺酰基香豆素的简便途径。在反应过程中，将原位生成2-（烯丙氧基）芳基，将其分子内加成双键以提供烷基中间体。进一步插入二氧化硫将产生烷基磺酰基基团。随后与丙酸芳基酯的组合将通过自由基环化和重排提供磺酰基桥连的二氢苯并呋喃和香豆素衍生物。

更新日期：2017-11-22

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