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Synthesis of 3-((arylsulfonyl)methyl)indolin-2-ones via insertion of sulfur dioxide using anilines as the aryl source

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Abstract

Facile assembly of 3-((arylsulfonyl)methyl)indolin-2-ones via insertion of sulfur dioxide starting from anilines, N-arylacrylamides and DABCO·(SO2)2 is developed. This one-pot reaction proceeds efficiently in dichloroethane, leading to sulfonated oxindoles in good yields. Anilines serve as the aryl source, and the in situ generated sulfonyl radicals from sulfur dioxide as the key intermediates are trapped by N-arylacrylamides to provide the corresponding products. Additionally, a broad reaction scope is observed under mild conditions.

Graphical abstract: Synthesis of 3-((arylsulfonyl)methyl)indolin-2-ones via insertion of sulfur dioxide using anilines as the aryl source

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Publication details

The article was received on 26 Jan 2017, accepted on 16 Feb 2017 and first published on 17 Feb 2017


Article type: Research Article
DOI: 10.1039/C7QO00075H
Citation: Org. Chem. Front., 2017, Advance Article
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    Synthesis of 3-((arylsulfonyl)methyl)indolin-2-ones via insertion of sulfur dioxide using anilines as the aryl source

    T. Liu, D. Zheng and J. Wu, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00075H

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