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Synthesis of polyfluorinated 4-phenyl-3,4-dihydroquinolin-2-ones and quinolin-2-ones via superacidic activation of N-(polyfluorophenyl)cinnamamides

✍ Scribed by Larisa Yu. Safina; Galina A. Selivanova; Konstantin Yu. Koltunov; Vitalij D. Shteingarts

Book ID: 104096770
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 200 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.07.013

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✦ Synopsis

The cyclization reactions of a series of polyfluorocinnamanilides in triflic acid (CF 3 SO 3 H) yield 4-phenyl-3,4-dihydroquinolin-2-ones, which include a polyfluorinated benzene moiety as a part of the quinoline scaffold. These compounds undergo dehydrophenylation in the presence of AlCl 3 to give the corresponding polyfluoroquinolin-2-ones which are converted into polyfluorinated 2-chloroquinolines on treatment with POCl 3 . A mechanism for the cyclization reaction presuming the intermediacy of a superelectrophilic O,C-diprotonated form of the starting material is suggested.

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