Synthesis of 2-Aryl-Substituted Indole-3-acetic Acid Derivatives via Intramolecular Imino-Stetter Reaction of Aldimines with Cyanide

Seong Jong Lee, Hong Ahn Seo, Cheol Hong Cheon

    Research output: Contribution to journalArticlepeer-review

    43 Citations (Scopus)

    Abstract

    A general method to generate umpolung of aldimines with cyanide was developed via the addition of cyanide to aldimines followed by a proton transfer from the carbon atom to the nitrogen atom in the resulting cyanide adducts. This novel method was successfully applied to the first imino-Stetter reaction of aldimines obtained from 2-aminocinnamic acid derivatives and aromatic aldehydes with cyanide, affording 2-aryl-substituted indole-3-acetic acid derivatives. Furthermore, the usefulness of this method was successfully demonstrated by the synthesis of an FPTase inhibitor, one of the biologically important 2-arylindole-3-acetic acid derivatives. (Figure presented.).

    Original languageEnglish
    Pages (from-to)1566-1570
    Number of pages5
    JournalAdvanced Synthesis and Catalysis
    Volume358
    Issue number10
    DOIs
    Publication statusPublished - 2016 May 19

    Bibliographical note

    Publisher Copyright:
    © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

    Keywords

    • 2-arylindole-3-acetic acid derivatives
    • aldimines
    • cyanide
    • imino-Stetter reaction
    • umpolung

    ASJC Scopus subject areas

    • Catalysis
    • Organic Chemistry

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