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Issue 24, 2016
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Stereoselective synthesis of thiazino[4,3-a]indoles using the thia-Pictet–Spengler reaction of indoles bearing N-tethered thiols and vinylogous thiocarbonates

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Abstract

An inter- as well as intra-molecular thia-Pictet–Spengler cyclization of N-tethered thiols and vinylogous thiocarbonates is described for the stereoselective synthesis of N-fused thiazinoindole derivatives. The strategy is extended to one-pot, sequential Friedel–Crafts alkylation – Pictet–Spengler cyclization and the synthesis of thiazino-oxepino-indole.

Graphical abstract: Stereoselective synthesis of thiazino[4,3-a]indoles using the thia-Pictet–Spengler reaction of indoles bearing N-tethered thiols and vinylogous thiocarbonates

  • This article is part of the themed collection: New Talent
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Publication details

The article was received on 05 Mar 2016, accepted on 16 Mar 2016 and first published on 17 Mar 2016


Article type: Communication
DOI: 10.1039/C6OB00501B
Citation: Org. Biomol. Chem., 2016,14, 5586-5590

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    Stereoselective synthesis of thiazino[4,3-a]indoles using the thia-Pictet–Spengler reaction of indoles bearing N-tethered thiols and vinylogous thiocarbonates

    S. J. Gharpure and S. K. Nanda, Org. Biomol. Chem., 2016, 14, 5586
    DOI: 10.1039/C6OB00501B

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