In view of the considerable importance of thiadiazoles and thiazolidinones, which are the core structures in a variety of pharmaceuticals with a broad spectrum of biological activity. Synthesis of series of potential biological active 1, 3, 4 thiadiazole linked 4 thiazolidinone derivatives were obtained via a multistep synthesis sequence with a simple and convenient approach by using substituted benzoic acids, which are expected to possess enhanced antioxidant activity based on the literature survey reports. In the present study the initial compound, 5-phenyl-1, 3, 4-thiadiazol-2-amine was treated with different substituted aromatic aldehydes to produce Schiff base. The resulting Schiff base were subjected to addition reactions with thioglycolic acid to form title compounds of 2-phenyl-3-(5-phenyl-1,3,4-thiadiazol-2-yl)-1,3-thiazolidin-4-one. The structure of the synthesized compounds was characterised by FT-IR, H1NMR and mass spectral analysis. The synthesized compounds were tested for antioxidant activities with standard drug using DPPH method. The results of this study revealed that, among the compound tested for antioxidant activity, TZD 5 and TZD 3 exhibited promising antioxidant activity with the IC50 value 27.50µM and 28.00µM while the value of reference compound, ascorbic acid 29.2µM. The antioxidant screening results indicate that exciting DPPH radical scavenging activity was observed in compounds (TZD 3 and TZD 5) in comparison with standard ascorbic acid. These results may also provide some significance guidance for the development of new class antioxidant.