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Accessing Polysubstituted NH Pyrroles from Nitroalkenes via [4+2]‐Cycloaddition/Reductive Ring Contraction Strategy Научная публикация

Журнал European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Вых. Данные Год: 2024, Том: 27, Номер: 30, Номер статьи : e202400627, Страниц : DOI: 10.1002/ejoc.202400627
Авторы Pospelov Evgeny V. 1 , Zhirov Alexander V. 2,1 , Kamidolla Baglan 3,1 , Sukhorukov Alexey Yu. 1
Организации
1 Laboratory of organic and metal-organic nitrogen-oxygen systems N. D. Zelinsky Institute of Organic Chemistry Leninsky prospect, 47 Moscow 119991 Russia
2 Department of Chemistry M. V. Lomonosov Moscow State University Leninskie gory, 1, str. 3 Moscow 119991 Russia
3 Higher Chemical College D. Mendeleev University of Chemical Technology of Russia Miusskaya sq., 9 Moscow 125047 Russia

Реферат: A novel two-step access to polysubstituted pyrroles from nitroalkenes was developed. It involves [4+2]-cycloaddition with enol ethers to give six-membered cyclic nitronates followed by reductive ring contraction with Ra−Ni/AcOH or Ra−Ni/EtOH systems. The process is applicable to a variety of nitroalkenes and enol ethers bearing electron-rich and electron-poor substituents and functional groups. The anti-inflammatory drug Bimetopyrol and its structural modifications were successfully synthesized by the strategy developed. The key side products were identified that provided an insight into the mechanism of the developed reductive ring contraction to pyrroles.
Библиографическая ссылка: Pospelov E.V. , Zhirov A.V. , Kamidolla B. , Sukhorukov A.Y.
Accessing Polysubstituted NH Pyrroles from Nitroalkenes via [4+2]‐Cycloaddition/Reductive Ring Contraction Strategy
European Journal of Organic Chemistry. 2024. V.27. N30. e202400627 . DOI: 10.1002/ejoc.202400627 WOS Scopus OpenAlex
Идентификаторы БД:
Web of science: WOS:001281611400001
Scopus: 2-s2.0-85200024453
OpenAlex: W4399738664
Цитирование в БД:
БД Цитирований
OpenAlex 3
Scopus 4
Web of science 3
Альметрики: