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Synthesis of Functionalized Quinolines from 4-(o-Nitroaryl)-Substituted 3-Acyl-4,5-Dihydrofurans: Reductive Cyclization and C=C Bond Cleavageстатья
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: 12 июля 2017 г.
- Авторы: Zaytsev Sergey V., Villemson Elena V., Ivanov Konstantin L., Budynina Ekaterina M., Melnikov Mikhail Ya
- Журнал: European Journal of Organic Chemistry
- Том: 2017
- Номер: 19
- Год издания: 2017
- Издательство: John Wiley & Sons Ltd.
- Местоположение издательства: United Kingdom
- Первая страница: 2814
- Последняя страница: 2823
- DOI: 10.1002/ejoc.201700256
- Аннотация: A new synthetic approach to functionalized quinolines was developed based on the application of Zn-AcOH system as a simple and efficient reductive agent towards 4-(o-nitroaryl)-3-acyl-substituted 4,5-dihydrofurans. Reduction of 3-carbonyl-substituted dihydrofurans is accomplished by C=C double bond cleavage in the dihydrofuran ring and 1,6-cyclization leading to 3,4-dihydroquinolines. The latter can be easily oxidized to quinolines or reduced to tetrahydroquinolines. For dihydrofuran-3-carboxylates, reduction proceeds with retention of the dihydrofuran ring and affords a tricyclic dihydrofuroquinoline core under harsher conditions. The proposed general reaction pattern was supported by results of DFT calculations. Moreover, a similar reductive system can be successfully applied in the conversion of dihydrofuran acyclic precursors, -(o-nitroaryl) α,β-unsaturated carbonyl compounds, into quinoline derivatives.
- Добавил в систему: Иванов Константин Львович