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 |
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| 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 | ||||||
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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 OpenAlex
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 OpenAlex
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 |