Reaction of perfluoro-2-methylpent-2-ene and perfluoro-5-azanon-4-ene with aniline and its derivatives

Reaction of perfluoro-2-methylpent-2-ene (1) and perfluoro-5-azanon-4-ene (2) with aniline, 4-fluoroaniline, 4-methoxyaniline and 2,6-dimethylaniline in the presence of Et3N provides derivatives of quinoline and quinozaline, whereas reaction of 2 yields diazetine derivatives with 2- and 4-nitroanilines, 2,6-dichloroaniline and pentafluoroaniline. The structure of [2-(1,1,2,2,3,3,3-pentafluoroethyl)-3-trifluoromethyl-quinoline-4-yl]-phenylamine is confirmed by X-ray structural data. The routes of reactions and the 19F and 13C NMR spectral data of the products are discussed.