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Issue 90, 2018
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Expeditious synthesis of multisubstituted indoles via multiple hydrogen transfers

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Abstract

Described herein is the expeditious construction of multi-substituted indole skeletons via multiple hydrogen transfers. When ortho-amino ketoesters were treated with a catalytic amount of TiCl4 in the presence of 1.0 equivalent of dehydrating reagent, three types of hydrogen transfer processes ([1,5]-hydride shift, proton transfer, and [1,2]-hydride shift) occurred to give various 3-alkoxycarbonylindoles. Further study revealed that a [1,2]-alkyl shift instead of a [1,2]-hydride shift proceeded to afford 3-alkylindoles from the substrates with an amino group having tertiary carbons adjacent to a nitrogen atom.

Graphical abstract: Expeditious synthesis of multisubstituted indoles via multiple hydrogen transfers

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Publication details

The article was received on 29 Aug 2018, accepted on 02 Oct 2018 and first published on 02 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC07009A
Citation: Chem. Commun., 2018,54, 12686-12689
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    Expeditious synthesis of multisubstituted indoles via multiple hydrogen transfers

    T. Yoshida and K. Mori, Chem. Commun., 2018, 54, 12686
    DOI: 10.1039/C8CC07009A

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