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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Acknowledgement

This work was performed with financial support from the Russian Foundation for Basic Research (project No. 16-53-44027) and the Russian Science Foundation (project No. 14-13-00822).

The authors are grateful to the Chemical Service Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences for spectral studies and analytical support.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva, Novosibirsk, 630090, Russia

    Valentina T. Bauman & Elvira E. Shults

  2. Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, 54 Enkhtaivan Ave., Ulaanbaatar, Mongolia

    Jamsranjav Ganbaatar

  3. Novosibirsk National Research State University, 2 Pirogova St., Novosibirsk, 630090, Russia

    Elvira E. Shults

Authors
  1. Valentina T. Bauman
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  2. Jamsranjav Ganbaatar
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  3. Elvira E. Shults
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(8), 913–919

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Bauman, V.T., Ganbaatar, J. & Shults, E.E. Synthetic transformations of isoquinoline alkaloids: 1-(N-alkyl-1,2,3-triazol-4-yl)-6,18-endo-ethenodihydrothebainehydroquinones and triazolylnaphthohydroquinone-containing benzofuroazocines from thebaine. Chem Heterocycl Comp 53, 913–919 (2017). https://doi.org/10.1007/s10593-017-2145-2

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