Design, syntesis and structure of some derivates 1,3-thiazolidine-2,4-dione

Tiazolidini su skupina heterocikličkih organskih spojeva sa zasićenim peteročlanim prstenom koji sadrži tioestersku i amino skupinu na 1- i 3- položaju. 1,3-Tiazolidin-2,4-dioni i njegovi derivati su skupina spojeva s različitim mogućnostima heterocikličkih modifikacija. Najviše se istražuju zbog širokog spektra farmakoloških svojstava. Metilenska skupina na petom položaju 1,3-tiazolidin-2,4-diona je najreaktivnija. Zbog toga se većina modifikacija na prstenu 1,3-tiazolidin-2,4-diona odvija u petom položaju i pri tome nastaju novi spojevi. Ovim radom istaknuti su dizajn, sinteza i struktura nekih derivata 1,3-tiazolidin-2,4- diona. Kao efikasna metoda za sintezu nekih derivata 1,3-tiazolidin-2,4-diona pokazala se Knoevenagel-ova kondenzacija. Knoevenagel-ovom kondenzacijom aktivne metilenske skupine na 5- položaju u 1,3-tiazolidin-2,4-dionima sa aldehidima nastaju 5-ariliden-2,4- tiazolidindioni. Tijek reakcije je praćen tankoslojnom kromatografijom. Dobiveni spojevi su pročišćeni prekristalizacijom, određene su im točke tališta i elementarni sastav. Stuktura pojedinih spojeva potvrđena je na temelju podataka dobivenih elementarnom mikroanalizom 1H NMR i IR spektrometrijom.Thiazolidines are a group of heterocyclic organic compounds with saturated fivemembered ring containing tioether and amino group on the 1- and 3- position. 1,3-Thiazolidine-2,4-dione and its derivatives are a group of compounds with different capabilities of heterocyclic modifications. Most are investigated due to the wide spectrum of pharmacological properties. The most reactive group of 1,3-thiazolidine-2,4- dione is methylene group in the fifth position of the ring. Most modifications are performed in the fifth position of 1,3-thiazolidine-2,4-dione ring and therefore new compounds are synthesized. This paper highlights the design, synthesis and structure of some derivatives of 1,3- thiazolidine-2,4-dione. Knoevenagel condensation proved to be an efficient method for the synthesis of some derivatives of 1,3-thiazolidine-2,4-dione. Thiazolidinedione derivatives, 5 – aryliden-2,4-thiazolidinediones are synthesized by Knoevenagel condensation of an active methylene group with various aldehydes in the fifth position of the 1,3-thiazolidine-2,4-dione ring. The reactions were monitored using thin-layer chromatography. Products were purified by recrystalization, their melting points and elemental compositions were determined. Structure of the products has been deducted on the basis of elementary microanalysis data and 1H NMR and IR spectrometry