Synthetic Transformations of Sesquiterpene Lactones. 8*. Synthesis of 13-(2-Oxofuro- [2,3-d]pyrimidin-3(2H)-yl)eudesmanolides Научная публикация
| Журнал |
Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353 |
||||
|---|---|---|---|---|---|
| Вых. Данные | Год: 2014, Том: 50, Номер: 8, Страницы: 1063-1080 Страниц : DOI: 10.1007/s10593-014-1566-4 | ||||
| Ключевые слова | isoalantolactone; uracils; aza-Michael reaction; copper-catalyzed Mannich reaction; cross coupling; silver-catalyzed cyclization reaction | ||||
| Авторы |
|
||||
| Организации |
|
Реферат:
An aza-Michael reaction of isoalantolactone with 5-bromo- or 5-iodo-substituted uracils gave (11R)-13-[5-bromo(iodo)-2,4-dioxotetrahydropyrimidin-1-yl]eudesma-4(15)-en-8 beta,12-olides, which were highly active in Pd-catalyzed cross-coupling reaction with terminal alkynes. Copper-catalyzed Mannich reaction of (11R)-13-(5-ethynyl-2,4-dioxotetrahydropyrimidin-1-yl)eudesma-4(15)-en-8 beta,12-olide with secondary amines and formaldehyde was used for the synthesis of (11R)-13-[5-(diethyl-amino)propynyl]-, (11R)-13-[5-(pyrrolidinyl-1-yl)propynyl]-, (11R)-13-[5-(4-oxopiperidin-1-yl)-propynyl]-, (11R)-13-[5-(4-methylpiperazin-1-yl)propynyl]-, and (11R)-13-(5-{[2-(pyridin-3-yl)piperidin-1-yl]propynyl}-2,4-dioxotetrahydropyrimidin-1-yl)eudesmanolides. The treatment of 13-[5(propargyl-amino)tetrahydropyrimidin-1-yl]eudesmanolides with silver nitrate led to the corresponding (11R)-13-(2-oxofuro[2,3-d]pyrimidin-3(2H)-yl)eudesmanolides. The structures of two compounds were proved by X-ray structural analysis.
Библиографическая ссылка:
Patrushev S.S.
, Shakirov M.M.
, Rybalova T.V.
, Shults E.E.
Synthetic Transformations of Sesquiterpene Lactones. 8*. Synthesis of 13-(2-Oxofuro- [2,3-d]pyrimidin-3(2H)-yl)eudesmanolides
Chemistry of Heterocyclic Compounds. 2014. V.50. N8. P.1063-1080. DOI: 10.1007/s10593-014-1566-4 WOS Scopus РИНЦ OpenAlex
Synthetic Transformations of Sesquiterpene Lactones. 8*. Synthesis of 13-(2-Oxofuro- [2,3-d]pyrimidin-3(2H)-yl)eudesmanolides
Chemistry of Heterocyclic Compounds. 2014. V.50. N8. P.1063-1080. DOI: 10.1007/s10593-014-1566-4 WOS Scopus РИНЦ OpenAlex
Даты:
| Опубликована online: | 8 окт. 2014 г. |
| Опубликована в печати: | 1 нояб. 2014 г. |
Идентификаторы БД:
| Web of science: | WOS:000344093400001 |
| Scopus: | 2-s2.0-84921938213 |
| РИНЦ: | 24030955 |
| OpenAlex: | W2010776628 |