2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
| Заглавие |
2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives
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| Автор |
Obydennov, D. L.
Nigamatova, D. I. Shirinkin, A. S. Melnikov, O. E. Fedin, V. V. Usachev, S. A. Simbirtseva, A. E. Kornev, M. Y. Sosnovskikh, V. Y. |
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| Тематика |
1,6-CONJUGATE ADDITION
4-PYRONE CYCLOADDITION DMF-DMA ENAMINATION FLUOROPHORE MEROCYANINE SOLVATOCHROMISM PYRANS PYRONES PYRAN DERIVATIVE PYRONE DERIVATIVE |
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| Описание |
A straightforward approach for the construction of the new class of conjugated pyrans based on enamination of 2-methyl-4-pyrones with DMF-DMA was developed. 2-(2-(Dimethylamino)vinyl)-4-pyrones are highly reactive substrates that undergo 1,6-conjugate addition/elimination or 1,3-dipolar cycloaddition/elimination followed by substitution of the dimethylamino group without ring opening. This strategy includes selective transformations leading to conjugated and isoxazolyl-substituted 4-pyrone structures. The photophysical properties of the prepared 4-pyrones were determined in view of further design of novel merocyanine fluorophores. A solvatochromism was found for enamino-substituted 4-pyrones accompanied by a strong increase in fluorescence intensity in alcohols. The prepared conjugated structures demonstrated valuable photophysical properties, such as a large Stokes shift (up to 204 nm) and a good quantum yield (up to 28%). © 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 12 December 2022)). |
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| Дата |
2024-04-08T11:06:40Z
2024-04-08T11:06:40Z 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 |
Obydennov, DL, Nigamatova, DI, Shirinkin, AS, Melnikov, OE, Fedin, VV, Usachev, SA, Simbirtseva, AE, Kornev, MY & Sosnovskikh, VY 2022, '2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives', Molecules, Том. 27, № 24, 8996. https://doi.org/10.3390/molecules27248996
Obydennov, D. L., Nigamatova, D. I., Shirinkin, A. S., Melnikov, O. E., Fedin, V. V., Usachev, S. A., Simbirtseva, A. E., Kornev, M. Y., & Sosnovskikh, V. Y. (2022). 2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives. Molecules, 27(24), [8996]. https://doi.org/10.3390/molecules27248996 1420-3049 Final All Open Access; Gold Open Access; Green Open Access https://www.mdpi.com/1420-3049/27/24/8996/pdf?version=1671610007 https://www.mdpi.com/1420-3049/27/24/8996/pdf?version=1671610007 http://elar.urfu.ru/handle/10995/131334 10.3390/molecules27248996 85144489390 000904269600001 |
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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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