Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones

Alexander V. Aksenov; Alexander N. Smirnov; Nicolai A. Aksenov; Inna V. Aksenova; Liliya V. Frolova; Alexander Kornienko; Igor V. Magedov; Michael Rubin

doi:10.1039/C3CC45696J

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Metal-free transannulation reaction of indoles with nitrostyrenes: a simple practical synthesis of 3-substituted 2-quinolones

Alexander V. Aksenov, Alexander N. Smirnov, Nicolai A. Aksenov, Inna V. Aksenova, Liliya V. Frolova, Alexander Kornienko, Igor V. Magedov and Michael Rubin

Chem. Commun., 2013,49, 9305-9307

DOI: 10.1039/C3CC45696J
Received 26 Jul 2013, Accepted 09 Aug 2013
First published online 13 Aug 2013

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3-Substituted 2-quinolones are obtained via a novel, metal-free transannulation reaction of 2-substituted indoles with 2-nitroalkenes in polyphosphoric acid. The reaction can be used in conjunction with the Fisher indole synthesis offering a practical three-component heteroannulation methodology to produce 2-quinolones from arylhydrazines, 2-nitroalkenes and acetophenone.