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://www.scopus.com/record/display.uri?eid=2-s2.0-84921311817&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=3a73d74600efaa7e503fb84a84113fb0&sot=afnl&sdt=sisr&cluster=scopubyr%2c%222015%22%2ct&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&ref=%28Metal-free+ring+expansion+of+indoles+with+nitroalkenes%3a+A+simple%2c+modular+approach+to+3-substituted+2-quinolones%29&relpos=4&citeCnt=23&searchTerm= https://dspace.ncfu.ru/handle/20.500.12258/4247
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spelling	ir-20.500.12258-42472020-09-11T14:38:23Z Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones 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. Ketones Arylhydrazines Cascade transformations Electron-rich arenes Modular approach Polyphosphoric acids Ring expansion Synthesis (chemical) 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 2019-02-11T12:23:38Z 2019-02-11T12:23:38Z 2015 Статья Aksenov, A.V., Smirnov, A.N., Aksenov, N.A., Aksenova, I.V., Matheny, J.P., Rubin, M. Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones // RSC Advances. - 2015. - Volume 5. - Issue 12. - Pages 8647-8656 https://www.scopus.com/record/display.uri?eid=2-s2.0-84921311817&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=3a73d74600efaa7e503fb84a84113fb0&sot=afnl&sdt=sisr&cluster=scopubyr%2c%222015%22%2ct&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&ref=%28Metal-free+ring+expansion+of+indoles+with+nitroalkenes%3a+A+simple%2c+modular+approach+to+3-substituted+2-quinolones%29&relpos=4&citeCnt=23&searchTerm= http://hdl.handle.net/20.500.12258/4247 en RSC Advances application/pdf application/pdf Royal Society of Chemistry
institution	СКФУ
collection	Репозиторий
language	English
topic	Ketones Arylhydrazines Cascade transformations Electron-rich arenes Modular approach Polyphosphoric acids Ring expansion Synthesis (chemical)
spellingShingle	Ketones Arylhydrazines Cascade transformations Electron-rich arenes Modular approach Polyphosphoric acids Ring expansion Synthesis (chemical) 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. Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
description	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
format	Статья
author	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.
author_facet	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.
author_sort	Aksenov, A. V.
title	Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
title_short	Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
title_full	Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
title_fullStr	Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
title_full_unstemmed	Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
title_sort	metal-free ring expansion of indoles with nitroalkenes: a simple, modular approach to 3-substituted 2-quinolones
publisher	Royal Society of Chemistry
publishDate	2019
url	https://www.scopus.com/record/display.uri?eid=2-s2.0-84921311817&origin=resultslist&sort=plf-f&src=s&nlo=1&nlr=20&nls=afprfnm-t&affilName=north+caucasus+federal+university&sid=3a73d74600efaa7e503fb84a84113fb0&sot=afnl&sdt=sisr&cluster=scopubyr%2c%222015%22%2ct&sl=53&s=%28AF-ID%28%22North+Caucasus+Federal+University%22+60070541%29%29&ref=%28Metal-free+ring+expansion+of+indoles+with+nitroalkenes%3a+A+simple%2c+modular+approach+to+3-substituted+2-quinolones%29&relpos=4&citeCnt=23&searchTerm= https://dspace.ncfu.ru/handle/20.500.12258/4247
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Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones

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