Synthesis of 2-Substituted Tryptamines via Cyanide-Catalyzed Imino-Stetter Reaction

Hyung Joo Kim, Cheol Hong Cheon

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)

    Abstract

    Herein, we describe the development of a two-step protocol for the synthesis of 2-substituted tryptamine derivatives from 2-aminocinnamyl nitriles and aldehydes. The cyanide-catalyzed imino-Stetter reaction of 2-aminocinnamyl nitriles and aldehydes provided 2-substituted indole-3-acetonitrile derivatives. Subsequent reduction of the nitrile group afforded the desired 2-substituted tryptamine derivatives. The utility of this protocol was demonstrated in the synthesis of a potential inhibitor of 15-lipoxygenase. Furthermore, the resulting 2-substituted indole-3-acetonitriles were converted to several 2,3-disubstituted indole derivatives upon transformation of the nitrile group into other functional groups.

    Original languageEnglish
    Pages (from-to)2103-2107
    Number of pages5
    JournalAsian Journal of Organic Chemistry
    Volume9
    Issue number12
    DOIs
    Publication statusPublished - 2020 Dec

    Bibliographical note

    Funding Information:
    This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF‐2018R1D1A1A02086110 and NRF‐2014‐011165, Center for New Directions in Organic Synthesis).

    Publisher Copyright:
    © 2020 Wiley-VCH GmbH

    Keywords

    • Cyanide
    • Imino-Stetter reaction
    • Indoles
    • Nitrile
    • Tryptamines

    ASJC Scopus subject areas

    • Organic Chemistry

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