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 cyclization reaction presuming the intermediacy of a superelectrophilic O,C-diprotonated form of the starting material is suggested.

中文翻译：

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N-（多氟苯基）肉桂酰胺的超酸性活化合成多氟4-苯基-3,4-二氢喹啉-2-酮和喹啉-2-酮

一系列多氟肉桂酸在三氟甲磺酸（CF ₃ SO ₃ H）中的环化反应产生4-苯基-3,4-二氢喹啉-2-酮，其中包括多氟苯部分作为喹啉骨架的一部分。这些化合物在AlCl ₃存在下进行脱氢苯基化反应，得到相应的多氟喹啉-2-酮，在用POCl ₃处理后将其转化为多氟2-氯喹啉。提出了一种环化反应的机理，该机理假定了超亲电的O，C-二质子化形式的起始原料为中间体。