Metal-free ring expansion of indoles with nitroalkenes: a simple, modular approach to 3-substituted 2-quinolones?
RSC Advances Pub Date: 2014-12-23 DOI: 10.1039/C4RA14406F
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.
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Journal Name：RSC Advances
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