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Ring-chain tautomerism in the products of the reaction between 5-substituted furfurylamines and anhydrides of α,β-unsaturated carboxylic acidsстатья
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: 23 марта 2017 г.
- Авторы: Fedor Zubkov I., Golubev Victor D., Zaytsev Vladimir P., Bakhanovich Olga V., Nikitina Evgeniya V., Khrustalev Victor N., Aysin Rinat R., Timofeeva Tatiana V., Novikov Roman A., Aleksey V.
- Журнал: Chemistry of Heterocyclic Compounds
- Том: 52
- Номер: 4
- Год издания: 2016
- Издательство: Kluwer Academic/Plenum Publishers
- Местоположение издательства: United States
- Первая страница: 225
- Последняя страница: 236
- DOI: 0009-3122/16/52(4)-0225
- Аннотация: The reactions of 5-substituted furfurylamines with anhydrides of α,β-unsaturated carboxylic acids (acryloyl chloride and maleicanhydride) were studied. The first step of the reaction mechanism involved acylation of furfurylamine nitrogen atom, followed by a stereospecific, spontaneous intramolecular Diels–Alder reaction at the furan ring of the N-furfurylamide intermediates. When the starting materials were 5-alkyl-substituted furfurylamines, the expected 1-oxo-2,3,7,7a-hexahydro-1Н-3а,6-epoxyisoindoles or the corresponding 7-carboxylic acids were obtained in up to 98% yields. The acylation of 5-aryl-substituted furfurylamines with maleic anhydride led to N-furfurylmaleic amides, which formed a dynamic equilibrium in solutions with adducts formed by intramolecular [4+2] cycloaddition, 3а,6-epoxyisoindole-7-carboxylic acids, as proved by NMR spectroscopy. X-ray structural analysis results show that these mixtures crystallized in the form of the cyclic tautomer.
- Добавил в систему: Айсин Ринат Равильевич
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