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Acid-catalyzed conversions of N-(4-nitrobenzylidene)-2-cyclopropyl And N-(4-nitrobenzylidene)-2-alkenylanilines. A new method for the synthesis of dihydroquinolines and quinolinesстатья
Информация о цитировании статьи получена из
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 28 мая 2015 г.
- Авторы: Trofimova E.V., Fedotov A.N., Mochalov S.S., Shabarov Y.S., Zefirov N.S.
- Журнал: Chemistry of Heterocyclic Compounds
- Том: 36
- Номер: 10
- Год издания: 2000
- Издательство: Kluwer Academic/Plenum Publishers
- Местоположение издательства: United States
- Первая страница: 1198
- Последняя страница: 1205
- DOI: 10.1023/A:1002824917758
- Аннотация: The acid-catalyzed conversions of N-(4-nitrobenzylidene)-2-cyclopropyl- and N-(4-nitrobenzylidene)-2-alkenylanilines have been studied. It has been established that the protonated azomethine unit of N-(4-nitrobenzylidene)-2-cyclopropylanilines is not capable of initiating intramolecular heterocyclization with participation of the three-membered ring. Conversion of N-(4-nitrobenzylidene)-2-(1-methylcyclopropyl)aniline to derivatives of quinoline is possible under the influence of concentrated H2SO4. Under the same conditions 2-methylcyclopropyl- and cyclopropyl-substituted Schiff’s bases form only the corresponding alkenylazomethines (isomerization of the three-membered ring). Under the influence of more moderate acids (trifluoroacetic, polyphosphoric) N-(4-nitrobenzylidene)-2-propenyl- and N-(4-nitrobenzylidene)-2-buten-2-yl)anilines are converted to the corresponding dihydroquinolines and quinolines in high yields. N-(4-Nitrobenzylidene)-2-(2,2- dimethylvinyl)aniline does not form derivatives of quinoline under the influence of the same acids in the given conditions.
- Добавил в систему: Зефиров Николай Серафимович