Reactions of Trifluorotriacetic Acid Lactone and Hexafluorodehydroacetic Acid with Amines: Synthesis of Trifluoromethylated 4-Pyridones and Aminoenones
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
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Reactions of Trifluorotriacetic Acid Lactone and Hexafluorodehydroacetic Acid with Amines: Synthesis of Trifluoromethylated 4-Pyridones and Aminoenones
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| Автор |
Fedin, V. V.
Usachev, S. A. Obydennov, D. L. Sosnovskikh, V. Y. |
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| Тематика |
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 |
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| Описание |
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.
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). |
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| Дата |
2024-04-08T11:06:36Z
2024-04-08T11:06:36Z 2022 |
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| Тип |
Article
Journal article (info:eu-repo/semantics/article) Published version (info:eu-repo/semantics/publishedVersion) |
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| Идентификатор |
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 1420-3049 Final All Open Access; Gold Open Access; Green Open Access https://www.mdpi.com/1420-3049/27/20/7098/pdf?version=1666692709 https://www.mdpi.com/1420-3049/27/20/7098/pdf?version=1666692709 http://elar.urfu.ru/handle/10995/131320 10.3390/molecules27207098 85140796209 000873058000001 |
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| Язык |
en
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| Связанные ресурсы |
info:eu-repo/grantAgreement/RSF//18-13-00186
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| Права |
Open access (info:eu-repo/semantics/openAccess)
cc-by https://creativecommons.org/licenses/by/4.0/ |
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| Формат |
application/pdf
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| Издатель |
MDPI
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| Источник |
Molecules
Molecules |
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