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Название: | Reactions of Trifluorotriacetic Acid Lactone and Hexafluorodehydroacetic Acid with Amines: Synthesis of Trifluoromethylated 4-Pyridones and Aminoenones |
Авторы: | Fedin, V. V. Usachev, S. A. Obydennov, D. L. Sosnovskikh, V. Y. |
Дата публикации: | 2022 |
Издатель: | MDPI |
Библиографическое описание: | Fedin, VV, Usachev, SA, Obydennov, DL & Sosnovskikh, VY 2022, 'Reactions of Trifluorotriacetic Acid Lactone and Hexafluorodehydroacetic Acid with Amines: Synthesis of Trifluoromethylated 4-Pyridones and Aminoenones', Molecules, Том. 27, № 20, 7098. https://doi.org/10.3390/molecules27207098 Fedin, V. V., Usachev, S. A., Obydennov, D. L., & Sosnovskikh, V. Y. (2022). Reactions of Trifluorotriacetic Acid Lactone and Hexafluorodehydroacetic Acid with Amines: Synthesis of Trifluoromethylated 4-Pyridones and Aminoenones. Molecules, 27(20), [7098]. https://doi.org/10.3390/molecules27207098 |
Аннотация: | Dehydroacetic acid and triacetic acid lactone are known to be versatile substrates for the synthesis of a variety of azaheterocycles. However, their fluorinated analogs were poorly described in the literature. In the present work, we have investigated reactions of trifluorotriacetic acid lactone and hexafluorodehydroacetic acid with primary amines, phenylenediamine, and phenylhydrazine. While hexafluorodehydroacetic acid reacted the same way as non-fluorinated analog giving 2,6-bis(trifluoromethyl)-4-pyridones, trifluorotriacetic acid lactone had different regioselectivity of nucleophilic attack compared to the parent structure, and corresponding 3-amino-6,6,6-trifluoro-5-oxohex-3-eneamides were formed as the products. In the case of binucleophiles, further cyclization took place, forming corresponding benzodiazepine and pyrazoles. The obtained 2,6-bis(trifluoromethyl)-4-pyridones were able to react with active methylene compounds giving fluorinated merocyanine dyes. © 2022 by the authors. |
Ключевые слова: | 4-HYDROXY-2-PYRONE 4-PYRIDONE AMINOENONE REGIOSELECTIVE REACTIONS TRIFLUOROMETHYLATED HETEROCYCLES ACIDS AMINES BENZODIAZEPINES COLORING AGENTS LACTONES PHENYLENEDIAMINES PHENYLHYDRAZINES PYRAZOLES PYRIDONES 4-PYRIDONE ACID AMINE BENZODIAZEPINE DERIVATIVE COLORING AGENT DIPYRONE LACTONE PHENYLENEDIAMINE DERIVATIVE PHENYLHYDRAZINE DERIVATIVE PYRAZOLE DERIVATIVE |
URI: | http://elar.urfu.ru/handle/10995/131320 |
Условия доступа: | info:eu-repo/semantics/openAccess cc-by |
Текст лицензии: | https://creativecommons.org/licenses/by/4.0/ |
Идентификатор SCOPUS: | 85140796209 |
Идентификатор WOS: | 000873058000001 |
Идентификатор PURE: | 31572232 f08fa5c3-4b8b-4c71-b4e6-2c0c8e51c848 |
ISSN: | 1420-3049 |
DOI: | 10.3390/molecules27207098 |
Сведения о поддержке: | Russian Science Foundation, RSF, (18-13-00186) This research was funded by the Russian Science Foundation, grant number 18-13-00186 (https://rscf.ru/project/18-13-00186/ accessed on 18 October 2022). |
Карточка проекта РНФ: | 18-13-00186 |
Располагается в коллекциях: | Научные публикации ученых УрФУ, проиндексированные в SCOPUS и WoS CC |
Файлы этого ресурса:
Файл | Описание | Размер | Формат | |
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2-s2.0-85140796209.pdf | 2,62 MB | Adobe PDF | Просмотреть/Открыть |
Лицензия на ресурс: Лицензия Creative Commons