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Synthesis of Tetracyclic System of 2,4-Di(tert-Butyl)-6,7-Dihydrofuro[2’,3’:3,4]cyclohepta[1,2-b]indoleстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 18 июля 2013 г.
- Авторы: Butin Alexander V., Kostyukova Olga N., Tsiunchik Fatima A., Uchuskin Maxim G., Serdyuk Olga V., Trushkov Igor V.
- Журнал: Journal of Heterocyclic Chemistry
- Том: 48
- Номер: 3
- Год издания: 2011
- Издательство: Heterocorporation
- Местоположение издательства: United States
- Первая страница: 684
- Последняя страница: 690
- DOI: 10.1002/jhet.635
- Аннотация: For the first time, tetracyclic compounds, namely, furo[20,30:3,4]cyclohepta[1,2-b]indoles were synthesized by recyclization of ortho-substituted aryldifurylmethanes containing tert-butyl groups at C5 positions of the furan rings. It was shown that [2-(benzoylamino)phenyl]bis(5-tert-butyl-2-furyl)methanes 12 are transformed into tetracycles 15 at room temperature under treatment with POCl3 in benzene solution containing some drops of water. The reaction proceeds via the intermediate formation of 1-benzoylamino-3-(5-tert-butyl-2-furyl)-2-(4,4-dimethyl-3-oxopentyl)indoles 14 which can be isolated from the reaction mixture. The method is very simple but its application is restricted due to side reactions if electron-releasing groups are present in 12. On the other hand, the decrease of electron density on furan ring in the starting compounds (for example, the use of [2-X-phenyl]difurylmethanes (where X = tosylamino or hydroxy group) prevents cyclization under the studied reaction conditions. As a result, corresponding ketones are formed as products of recyclization.
- Добавил в систему: Трушков Игорь Викторович