Sciact
  • EN
  • RU

Synthesis of 3-trimethylsiloxy-1-(furan-3-yl)butadiene and its reactions with dienophiles Научная публикация

Журнал Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353
Вых. Данные Год: 2016, Том: 52, Номер: 6, Страницы: 364-373 Страниц : DOI: 10.1007/s10593-016-1897-4
Ключевые слова dimethylbarbituric acid; furan-3-aldehyde; Meldrum's acid; siloxybutadienes; Diels-Alder reaction; X-ray structural analysis
Авторы Mironov Maxim E. 1,2 , Bagryanskaya Irina Yu. 1,2 , Shults Elvira E. 1,2
Организации
1 (Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrentieva Ave, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk Natl Res State Univ, 2 Pirogova St, Novosibirsk 630090, Russia

Реферат: 3-Trimethylsilyloxy-1-(furan-3-yl)butadiene was synthesized and studied in reactions with 2,2-dimethyl-5-methylidene-1,3-dioxane-4,6-diones, 5-methylenepyrimidine-2,4,6-triones, as well as with imines. Reactions with dienophiles containing an exo-methylene double bond in the presence of L-proline occurred regio- and stereoselectively with the formation of 7-(furan-3-yl)spiro[5,5]undecane-1,5,9-triones or 7-(furan-3-yl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraones. The reaction of diene with methylene imine, obtained from L-phenylalanine methyl ester and formaldehyde, in the presence of Lewis acids led to the formation of 2-(furan-3-yl)piperidin-4-one or the product of ene reaction, methyl (2S)-2-{[(4E)-5-(furan-3-yl)-3-oxopent-4-en-1-yl]amino}-3-phenylpropanoate. The structures of three compounds were confirmed by X-ray structural analysis.
Библиографическая ссылка: Mironov M.E. , Bagryanskaya I.Y. , Shults E.E.
Synthesis of 3-trimethylsiloxy-1-(furan-3-yl)butadiene and its reactions with dienophiles
Chemistry of Heterocyclic Compounds. 2016. V.52. N6. P.364-373. DOI: 10.1007/s10593-016-1897-4 WOS Scopus РИНЦ OpenAlex
Даты:
Опубликована в печати: 1 июн. 2016 г.
Опубликована online: 9 авг. 2016 г.
Идентификаторы БД:
Web of science: WOS:000382138200005
Scopus: 2-s2.0-85028271715
РИНЦ: 41788374
OpenAlex: W2509202637
Цитирование в БД:
БД Цитирований
Web of science 3
Scopus 3
РИНЦ 4
OpenAlex 3
Альметрики: