SYNTHETIC TRANSFORMATIONS OF ISOQUINOLINE ALKALOIDS: 1-(<i>N</i>-ALKYL-1,2,3-TRIAZOL-4-YL)-6,18-<i>endo</i>-ETHENODIHYDROTHEBAINEHYDROQUINONES AND TRIAZOLYLNAPHTHOHYDROQUINONE-CONTAINING BENZOFUROAZOCINES FROM THEBAINE

Authors

  • Валентина Т. Бауман N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva, Novosibirsk 630090
  • Жамсранжав Ганбаатар Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, 54 Enkhtaivan Ave., Ulaanbaatar,
  • Эльвира Э. Шульц Novosibirsk National Research State University, 2 Pirogova St., Novosibirsk 630090

DOI:

https://doi.org/10.1007/3745

Keywords:

benzofuroazocines, dihydrothebainehydroquinone, thebaine, 1, 2, 3-triazoles, Cu(I)-catalyzed reactions, retro-cleavage

Abstract

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.

Authors: Valentina T. Bauman, Jamsranjav Ganbaatar, Elvira E. Shults*

Author Biographies

Валентина Т. Бауман, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva, Novosibirsk 630090

Научный сотрудник лаборатории медицинской химии

Жамсранжав Ганбаатар, Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences, 54 Enkhtaivan Ave., Ulaanbaatar,

Научный сотрудник института химии и химической технологии Монгольской академии наук

Эльвира Э. Шульц, Novosibirsk National Research State University, 2 Pirogova St., Novosibirsk 630090

зав. Лабораторией медицинской химии

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Published

2017-10-04

Issue

Vol. 53 No. 8 (2017)

Section

Original Papers