Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
| Заглавие |
Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters
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| Автор |
Kochnev, I. A.
Barkov, A. Y. Simonov, N. S. Ulitko, M. V. Zimnitskiy, N. S. Korotaev, V. Y. Sosnovskikh, V. Y. |
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| Тематика |
3-NITRO-2H-CHROMENES
AZOMETHINE YLIDES CHROMENO[3,4-C]PYRROLIDINES CYTOTOXICITY MICHAEL ADDITION/MANNICH REACTION SEQUENCE AZO COMPOUNDS BENZOPYRANS HUMANS PYRROLIDINES 5,7-DIMETHOXY-2-METHYL-2H-BENZOPYRAN AZO COMPOUND AZOMETHINE BENZOPYRAN DERIVATIVE PYRROLIDINE DERIVATIVE HUMAN |
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| Описание |
The AgOAc-catalysed reaction of 3-nitro-2-phenyl-2H-chromenes with stabilized azomethine ylides generated from the imines based on methyl glycinate and arylaldehydes leads to a mixture of endo and endo’ isomers of the corresponding chromeno[3,4-c]pyrrolidines in a ratio of 2.0–2.3:1 in 85–93% total yields as a result of a Michael addition/Mannich reaction sequence. In a similar reaction involving 2-trifluoromethyl-3-nitro-2H-chromenes, only endo chromeno[3,4-c]pyrrolidines are formed in 85–94% yields. 3-Nitro-2-(trichloromethyl)-2H-chromenes under the same conditions react with these azomethine ylides to give the corresponding Michael adducts as individual anti-isomers with the cis,trans-configuration of the chromane ring in 40–67% yields. Some 4-CF3-substituted chromano[3,4-c]pyrrolidines exhibited high cytotoxic activity against HeLa human cervical carcinoma cells. © 2022 by the authors.
Russian Foundation for Basic Research, РФФИ, (20-03-00716) Ministry of Education and Science of the Russian Federation, Minobrnauka, (FEUZ-2020-0052) This research was funded by the Russian Foundation for Basic Research (project 20-03-00716) and the Ministry of Science and Higher Education of the Russian Federation (project FEUZ-2020-0052). |
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| Дата |
2024-04-08T11:06:41Z
2024-04-08T11:06:41Z 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 |
Kochnev, IA, Barkov, AY, Simonov, NS, Ulitko, MV, Zimnitskiy, NS, Korotaev, VY & Sosnovskikh, VY 2022, 'Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters', Molecules, Том. 27, № 24, 8983. https://doi.org/10.3390/molecules27248983
Kochnev, I. A., Barkov, A. Y., Simonov, N. S., Ulitko, M. V., Zimnitskiy, N. S., Korotaev, V. Y., & Sosnovskikh, V. Y. (2022). Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters. Molecules, 27(24), [8983]. https://doi.org/10.3390/molecules27248983 1420-3049 Final All Open Access; Gold Open Access; Green Open Access https://www.mdpi.com/1420-3049/27/24/8983/pdf?version=1671193264 https://www.mdpi.com/1420-3049/27/24/8983/pdf?version=1671193264 http://elar.urfu.ru/handle/10995/131337 10.3390/molecules27248983 85144511486 000904212300001 |
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| Язык |
en
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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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MDPI
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| Источник |
Molecules
Molecules |
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