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

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

Журнал

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Вых. Данные

Год: 2017, Том: 53, Номер: 8, Страницы: 913-919 Страниц : DOI: 10.1007/s10593-017-2145-2

Ключевые слова

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

Авторы

Bauman Valentina T. ¹ , Ganbaatar Jamsranjav ² , Shults Elvira E. ^1,3

Организации

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

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.

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

Опубликована в печати:	1 авг. 2017 г.
Опубликована online:	3 окт. 2017 г.

Web of science:	WOS:000413601600016
Scopus:	2-s2.0-85030327473
РИНЦ:	31073709
OpenAlex:	W2761510899

БД	Цитирований
Web of science	2
Scopus	2
РИНЦ	2
OpenAlex	2