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Issue 28, 2017
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Intermolecular sulfenoamination of alkenes with sulfonamides and N-sulfanylsuccinimides to access β-sulfonylamino sulfides and dihydrobenzothiazines

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Abstract

An acid-catalyzed intermolecular sulfenoamination reaction of alkenes is developed with sulfonamides as the nitrogen source and N-sulfanylsuccinimides as the sulfur source. This methodology provides a straightforward and general way to synthesize various β-sulfonylamino sulfides with high regio- and diastereoselectivity. The developed method was coupled with intramolecular C–N coupling in a one-pot procedure to afford a series of dihydrobenzothiazine derivatives, a kind of important heterocycle used as biologically active compounds in medicinal chemistry.

Graphical abstract: Intermolecular sulfenoamination of alkenes with sulfonamides and N-sulfanylsuccinimides to access β-sulfonylamino sulfides and dihydrobenzothiazines

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Publication details

The article was received on 18 May 2017, accepted on 22 Jun 2017 and first published on 26 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01225J
Citation: Org. Biomol. Chem., 2017,15, 5983-5992
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    Intermolecular sulfenoamination of alkenes with sulfonamides and N-sulfanylsuccinimides to access β-sulfonylamino sulfides and dihydrobenzothiazines

    T. Liu, J. Tian, W. Gao, H. Chang, Q. Liu, X. Li and W. Wei, Org. Biomol. Chem., 2017, 15, 5983
    DOI: 10.1039/C7OB01225J

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