One-pot cascade synthesis of fluorinated thiazolidine-, thiazoline- and thiazole-5-carboxylic acid esters from N-monosubstituted perfluoroalkanethioamides

Abstract

The synthesis of new fluorinated thiazolidine-, thiazoline- and thiazole-5-carboxylic acid esters was performed via a one-pot cascade heterocyclization reaction of N-monosubstituted perfluoroalkanethioamides with methyl bromoacetate in the presence of 1,8-diazabicyclo[5.4.0]undec‑7-ene. The structures of fluorine-containing 1,3-thiazolidine and 1,3-thiazole derivatives have been determined by X-ray diffraction analysis. The plausible reaction pathways leading to the formation of various products are discussed. It was shown that the nature of the substituent at the nitrogen atom of thioamides, perfluoroalkyl chain length and the amount of the base significantly affect the reaction outcome.