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Synthesis of N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl-N,N-dialkylanilines

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Abstract

An efficient and metal-free approach to N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles from 2-alkynyl-N,N-dialkylanilines has been developed. In the presence of iodine and tert-butylhydroperoxide (TBHP), a variety of 2-alkynyl-N,N-dialkylanilines underwent a cascade radical annulation to yield 3-arylsulfonylindoles. In contrast, 3-arylsulfanylindoles were conveniently prepared by iodine mediated electrophilic annulation reactions. The present protocol uses the economical and environmentally friendly I2–TBHP or I2 system, and potentially bioactive N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles with various functional groups were successfully synthesized in moderate to good yields.

Graphical abstract: Synthesis of N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl-N,N-dialkylanilines

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Publication details

The article was received on 15 Feb 2017, accepted on 29 Mar 2017 and first published on 03 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00366H
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis of N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl-N,N-dialkylanilines

    J. Meesin, M. Pohmakotr, V. Reutrakul, D. Soorukram, P. Leowanawat and C. Kuhakarn, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00366H

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