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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 Full article

Journal Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353
Output data Year: 2017, Volume: 53, Number: 8, Pages: 913-919 Pages count : DOI: 10.1007/s10593-017-2145-2
Tags benzofuroazocines; dihydrothebainehydroquinone; thebaine; 1,2,3-triazoles; Cu(I)-catalyzed reactions; retro-cleavage
Authors Bauman Valentina T. 1 , Ganbaatar Jamsranjav 2 , Shults Elvira E. 1,3
Affiliations
1 (Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrentieva, Novosibirsk 630090, Russia
2 (Данные Web of science) Mongolian Acad Sci, Inst Chem & Chem Technol, 54 Enkhtaivan Ave, Ulaanbaatar, Mongolia
3 (Данные Web of science) Novosibirsk Natl Res State Univ, 2 Pirogova St, Novosibirsk 630090, Russia

Abstract: 1-Ethynyl-6,18-endo-ethenodihydrothebainehydroquinone reacted with azides in the presence of CuSO4 center dot 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.
Cite: 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
Chemistry of Heterocyclic Compounds. 2017. V.53. N8. P.913-919. DOI: 10.1007/s10593-017-2145-2 WOS Scopus РИНЦ
Dates:
Published print: Aug 1, 2017
Published online: Oct 3, 2017
Identifiers:
Web of science WOS:000413601600016
Scopus 2-s2.0-85030327473
Elibrary 31073709
OpenAlex W2761510899
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