Rudnichenko A. Synthesis and Properties of S,N-Heterocyclic Compounds Based on the Polyfluoroalkanthiocarboxylic Acids Amides

2-Polyfluoroalkyl-5-Metoxycarbonylmethylene-thiazolidin-4-ones were synthesized for the first time, as well as a number of their spirocyclic and condensed derivatives. It was established that the influence of polyfluoroalkyl substituent in 2 position results into increase of endocyclic C=N bond electrophylic properties. The reactions of 2-polyfluoroalkyl-2-metoxy-5-metoxycarbonylmethylene-1,3-thiazolidin-4-ones with PCl5, P4S10 and sodium hydroxide lead to the corresponding 4-chlorothiazolines, thiazolidine-4-thiones and thiazolidinacrylic acids formation. The reactions of 2-hydroxy-2-polyfluoroalkyl-5-metoxycarbonylmethylene-1,3-thiazolidin-4-ones and 2- hydroxy-2-polyfluoroalkyl-7,8-dimethyl-1-thia-2-aza-spiro[4,5]-dec-7-en-4-ones with ammonia and isobutylamine proceed with the opening of thiazolidine cycle and results into formation of 2-mercapto-2-carbamoylcarboxylic acids.