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Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones

Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones

3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can b...

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Главные авторы: Aksenov, A. V., Аксенов, А. В., Smirnov, A. N., Смирнов, А. Н., Aksenov, N. A., Аксенов, Н. А., Aksenova, I. V., Аксенова, И. В., Rubin, M. A., Рубин, М. А.
Формат: Статья
Язык:English
Опубликовано: Royal Society of Chemistry 2019
Темы:
Ketones
Arylhydrazines
Cascade transformations
Electron-rich arenes
Modular approach
Polyphosphoric acids
Ring expansion
Synthesis (chemical)
Online-ссылка:https://dspace.ncfu.ru/handle/20.500.12258/4247
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Краткое описание:3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation approach to 2-quinolones from arylhydrazines, 2-nitroalkenes, and acetophenone. An alternative entry to this chemistry employing the alkylation of electron-rich arenes and hetarenes with 1-(2-indolyl)-2-nitroalkene has also been demonstrated

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