Direct Mannich and nitro-Mannich reactions with non-activated imines: AgOTF-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines

Naoki Asao, Salprima Yudha S., Tsutomu Nogami, Yoshinori Yamamoto

    Research output: Contribution to journalArticlepeer-review

    197 Citations (Scopus)

    Abstract

    (Chemical Equation Presented) A variety of 1,2-dihydroisoquinoline derivatives 3 have been prepared in good to high yields by the AgOTf-catalyzed reaction of ortho-alkynylaryl aldimines 1 with various pronucleophiles 2 (see scheme). Treatment of 1 with a stoichiometric amount of AgOTf followed by protonation with TfOH produced 4, which suggests the formation of an isoquinolinium intermediate in the present direct addition reaction. Tf=trifluoromethanesulfonyl.

    Original languageEnglish
    Pages (from-to)5526-5528
    Number of pages3
    JournalAngewandte Chemie - International Edition
    Volume44
    Issue number34
    DOIs
    Publication statusPublished - 2005 Sep 2

    Keywords

    • Imines
    • Mannich reaction
    • Nitrogen heterocycles
    • Pronucleophiles
    • Synthetic methods

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

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