Intramolecular cyclization of polyfluoroalkyl-containing 2-(arylhydrazinylidene)-1,3-diketones

Abstract Refluxing of polyfluoroalkyl-containing 2-(arylhydrazinylidene)-1,3-diketones in dichloroalkanes in the presence of TiCl 4 gives 3-acyl-4-polyfluoroalkylcinnolines as a result of Friedel-Crafts intramolecular cyclization with the participation of polyfluoroacyl and arylhydrazone moieties. 2-(Arylhydrazinylidene)-3-phenyl-1-polyfluoroalkylpropan-1,3-diones in the presence of CF 3 SO 3 H in dichloromethane at −20…−30 °C undergo the competitive cyclization with the participation of polyfluoroacyl and benzoyl groups to form 3-hydroxy-2-(arylhydrazinylidene)-3-polyfluoroalkylindan-1-ones. The heating of 2-(arylhydrazinylidene)-1,3-diketones in polyphosphoric acid at 115…120 °C resulted in 2-polyfluoroalkyl-1-(2-arylhydrazinylidene)ethan-2-ones. The tuberculostatic activity of the obtained cinnolines and indanone was found to be at the level of pyrazinamide or higher. It was established that these compounds do not inhibit cholinesterases and have rather weak inhibitory activity against carboxylesterase. A high antiradical activity was shown for indanone.