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

doi:10.1007/s10593-017-2145-2

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

Результат исследования: Научные публикации в периодических изданиях › статья

Аннотация

[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.

Язык оригинала	английский
Страницы (с-по)	913-919
Число страниц	7
Журнал	Chemistry of Heterocyclic Compounds
Том	53
Номер выпуска	8
DOI	https://doi.org/10.1007/s10593-017-2145-2
Состояние	Опубликовано - 1 авг 2017

Доступ к документу

10.1007/s10593-017-2145-2

Link to publication in Scopus

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Цитировать

Bauman, V. T., Ganbaatar, J., & Shults, E. E. (2017). 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, 53(8), 913-919. https://doi.org/10.1007/s10593-017-2145-2

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

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.",

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",

author = "Bauman, {Valentina T.} and Jamsranjav Ganbaatar and Shults, {Elvira E.}",

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

В: Chemistry of Heterocyclic Compounds, Том 53, № 8, 01.08.2017, стр. 913-919.

Результат исследования: Научные публикации в периодических изданиях › статья

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AU - Bauman, Valentina T.

AU - Ganbaatar, Jamsranjav

AU - Shults, Elvira E.

PY - 2017/8/1

Y1 - 2017/8/1

N2 - [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.

AB - [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.

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KW - retro-cleavage

KW - thebaine

KW - ROUTE

KW - ANALOGS

KW - CLICK CHEMISTRY

KW - OPIOIDS

KW - LIGANDS

KW - ORVINOLS

KW - DIENE SYNTHESIS

KW - DERIVATIVES

KW - ANTINOCICEPTIVE ACTIVITIES

KW - HYBRIDS

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