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

…, GA Selivanova, KY Koltunov, VD Shteingarts

Index: Safina, Larisa Yu.; Selivanova, Galina A.; Koltunov, Konstantin Yu.; Shteingarts, Vitalij D. Tetrahedron Letters, 2009 , vol. 50, # 37 p. 5245 - 5247

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Citation Number: 12

Abstract

The cyclization reactions of a series of polyfluorocinnamanilides in triflic acid (CF3SO3H) 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 AlCl3 to give the corresponding polyfluoroquinolin-2-ones which are converted into polyfluorinated 2-chloroquinolines on treatment with POCl3. A mechanism for the ...