060 Cracow (Poland)
ketones, diketones and acetoacetic ethyl ester are known to react with trifluoromethylsulphenyl chloride to giveCtSCF3 substituted products [IJ, Th e reaction with CP SC1 was exten-3 ded to benzoylacetic ethyl ester, anilides of acetoacetic and benzoylacetic acids, and their Schiff bases, leading to&SCF3 substituted !3-dicarbonyl compounds or their nitrogen analogues Additionally, the reaction of CF3SSCF3 with C6H3COCH2COOC2H3 was investigated and the optimum conditions found to prepare oC-(trifluoromethylthiojbenzoylacetic ethyl ester in this way.
Ethyl esters of CG-(trifluoromethylthio)acetoacetic and &(trifluoromethylthio)benzoylacetic acids heated in a dimethylsulphoxide/water solution gave known trifluoromethylthioacetone and &(trifluoromethylthio)acetophenone respectively, while the splitting of these esters in a potassium hydroxide methanolic solution provided trifluoromethylthioacetic acid in a good yield, so this reaction could be treated as a new method for synthesis of CF SCH2COOH.
3 Anilides of Cb(trifluoromethylthio)acetoacetic and d-(trifluoromethylthio)benzoylacetic acids , and their Schiff bases were cyclized in acidic media to obtain 3-SCF 3 substituted derivatives of quinolones-2 and -4.
The structure of compounds synthesized was confirmed by elemental analyses, IR, MS, 'H and "F NMR spectra.