Please use this identifier to cite or link to this item: http://hdl.handle.net/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
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