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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

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Abstract

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.

Graphical abstract: Synthesis of 3-(((2,3-dihydrobenzofuran-3-yl)methyl)sulfonyl) coumarins through the reaction of 2-(allyloxy)anilines, sulfur dioxide, and aryl propiolates

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Publication details

The article was received on 01 Sep 2017, accepted on 04 Sep 2017 and first published on 05 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00787F
Citation: Org. Chem. Front., 2017, Advance Article
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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

    X. Wang, T. Liu, D. Zheng, Q. Zhong and J. Wu, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00787F

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