Standard

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.

In: Chemistry of Heterocyclic Compounds, Vol. 53, No. 8, 01.08.2017, p. 913-919.

Research output: Contribution to journal › Article › peer-review

Harvard

Bauman, VT, Ganbaatar, J & Shults, EE 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, vol. 53, no. 8, pp. 913-919. https://doi.org/10.1007/s10593-017-2145-2

APA

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

Vancouver

Bauman VT, Ganbaatar J, Shults EE. 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 Aug 1;53(8):913-919. doi: 10.1007/s10593-017-2145-2

Author

Bauman, Valentina T. ; Ganbaatar, Jamsranjav ; Shults, Elvira 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. In: Chemistry of Heterocyclic Compounds. 2017 ; Vol. 53, No. 8. pp. 913-919.

BibTeX

@article{9626ec1310744f1da545377d23731882,
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 = "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.}",
year = "2017",
month = aug,
day = "1",
doi = "10.1007/s10593-017-2145-2",
language = "English",
volume = "53",
pages = "913--919",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer New York",
number = "8",

}

RIS

TY - JOUR

T1 - Synthetic transformations of isoquinoline alkaloids: 1-(N-alkyl-1,2,3-triazol-4-yl)-6,18-endo-ethenodihydrothebainehydroquinones and triazolylnaphthohydroquinone-containing benzofuroazocines from thebaine

AU - Bauman, Valentina T.

AU - Ganbaatar, Jamsranjav

AU - Shults, Elvira E.

PY - 2017/8/1

Y1 - 2017/8/1

N2 - 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 - 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.

KW - 1,2,3-triazoles

KW - benzofuroazocines

KW - Cu(I)-catalyzed reactions

KW - dihydrothebainehydroquinone

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

UR - http://www.scopus.com/inward/record.url?scp=85030327473&partnerID=8YFLogxK

U2 - 10.1007/s10593-017-2145-2

DO - 10.1007/s10593-017-2145-2

M3 - Article

AN - SCOPUS:85030327473

VL - 53

SP - 913

EP - 919

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 8

ER -

ID: 9896365