Synthesis of some N-methyl-l,2,3,4-tetrahydroisoquinolines by Friedel-Crafts cyclisation using benzotriazole auxiliary

Cornelia Locher, Naseem H. Peerzada

    Research output: Contribution to journalComment/debate

    Abstract

    1-Hydroxymethylbenzotriazole reacts with phenylethylamines to give the respective N,N-bis(benzotriazol-1-
    ylmethyl)phenylethylamines, which are then subject to an intramolecular Friedel–Crafts cyclisation at room
    temperature to yield N-benzotriazol-1-ylmethyl-1,2,3,4-tetrahydroisoquinolines. These crystalline UV- and oxygenstable
    products can be reduced at room temperature to the corresponding N-methyl-1,2,3,4-tetrahydroisoquinolines
    using NaBH4. The method offers an elegant approach to a wide range of N-methylated 1,2,3,4-tetrahydroisoquinolines
    since it can be applied not only for the synthesis of 1,2,3,4-tetrahydroisoquinolines with electron-donating
    substituents on the aromatic moiety, but also for deactivated derivatives. All steps involved work under very mild
    conditions in high to excellent yields.
    Original languageEnglish
    Pages (from-to)179-184
    Number of pages6
    JournalJournal of the Chemical Society - Perkin Transactions 1
    Issue number2
    DOIs
    Publication statusPublished - 1999

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