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

ABSTRACT: 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.

SUBMITTER: Aksenov AV

PROVIDER: S-EPMC4945960 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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

Aksenov Alexander V AV Smirnov Alexander N AN Aksenov Nicolai A NA Aksenova Inna V IV Frolova Liliya V LV Kornienko Alexander A Magedov Igor V IV Rubin Michael M

Chemical communications (Cambridge, England) 20131001 81

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. ...[more]

PMID: 23999797

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