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A facile access to 2-substituted naphtho[2,3-g]quinoline-3-carboxylic acid esters via intramolecular cyclization and PyBOP-promoted functionalizationстатья
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: 7 октября 2020 г.
- Авторы: Litvinova Valeria A., Tikhomirov Alexander S., Ivanov Ivan V., Solovieva Svetlana E., Shchekotikhin Andrey E.
- Журнал: Tetrahedron
- Том: 76
- Номер: 36
- Год издания: 2020
- Издательство: Pergamon Press Ltd.
- Местоположение издательства: United Kingdom
- Номер статьи: 131418
- DOI: 10.1016/j.tet.2020.131418
- Аннотация: Heteroarene-fused derivatives of anthraquinone (anthracene-9,10-dione) represent an exceptionally productive class for the search for new anticancer compounds with improved properties. In this study, we report a convenient heterocyclization, which in three steps leads to 2-alkyl-, aryl-, or hydroxyl derivatives of 5,12-dimethoxynaphtho[2,3-g]quinoline-3-carboxylic acid esters. The scheme includes an alkylation of CH-acids with 2-(bromomethyl)-1,4-dimethoxy-3-nitroanthraquinone (8) followed by reductive cyclization and oxidative aromatization. To increase the series of naphtho[2,3-g]quinoline derivatives, a mild and effective PyBOP-mediated functionalization was developed, which introduced N-, S-, and O-nucleophiles at the 2-position of the quinoline core. We believe that this study allows to access a broad family of 2-substituted naphtho[2,3-g]quinolines and can be adapted for other quinoline derivatives or polyaromatic analogs.
- Добавил в систему: Литвинова Валерия Александровна