Synthetic transformations of isoquinoline alkaloids: 1-(N-alkyl-1,2,3-triazol-4-yl)-6,18-endo-ethenodihydrothebainehydroquinones and triazolylnaphthohydroquinone-containing benzofuroazocines from thebaine

Valentina T. Bauman, Jamsranjav Ganbaatar, Elvira E. Shults

    Research output: Contribution to journalArticlepeer-review

    Abstract

    [Figure not available: see fulltext.] 1-Ethynyl-6,18-endo-ethenodihydrothebainehydroquinone reacted with azides in the presence of CuSO4·5H2O and sodium ascorbate in DMF, forming the respective 1-(N-alkyl(arylalkyl)triazol-4-yl)-6,18-endo-ethenodihydrothebainehydroquinones, which underwent retrodiene cleavage upon heating in DMF, forming functionalized tetrahydrofuro[4,3,2-fg][3]benzazocines containing naphthohydroquinone and 1,2,3-triazolyl substituents.

    Original languageEnglish
    Pages (from-to)913-919
    Number of pages7
    JournalChemistry of Heterocyclic Compounds
    Volume53
    Issue number8
    DOIs
    Publication statusPublished - 1 Aug 2017

    Keywords

    • 1,2,3-triazoles
    • benzofuroazocines
    • Cu(I)-catalyzed reactions
    • dihydrothebainehydroquinone
    • retro-cleavage
    • thebaine
    • ROUTE
    • ANALOGS
    • CLICK CHEMISTRY
    • OPIOIDS
    • LIGANDS
    • ORVINOLS
    • DIENE SYNTHESIS
    • DERIVATIVES
    • ANTINOCICEPTIVE ACTIVITIES
    • HYBRIDS

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