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https://dspace.ncfu.ru/handle/20.500.12258/4247
Title: | Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones |
Authors: | 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. |
Keywords: | Ketones;Arylhydrazines;Cascade transformations;Electron-rich arenes;Modular approach;Polyphosphoric acids;Ring expansion;Synthesis (chemical) |
Issue Date: | 2015 |
Publisher: | Royal Society of Chemistry |
Citation: | 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 |
Series/Report no.: | RSC Advances |
Abstract: | 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 |
URI: | 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 |
Appears in Collections: | Статьи, проиндексированные в SCOPUS, WOS |
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scopusresults 793 .pdf Restricted Access | 64.46 kB | Adobe PDF | View/Open | |
WoS 513 .pdf Restricted Access | 767.46 kB | Adobe PDF | View/Open |
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