Abstract: In the present study, a series of novel N-substituted thiazolidine-2,4-dione was designed and further synthesized from their corresponding aldehydes according to Knoevenagel’s condensation method. The resulting 5-arylidinethiazolidine-2,4-dione was reacted with substituted aromatic acid to give 3-substituted 5-arylidinethiazolidine-2,4-dione. The structural eluciadtion of the compounds was based on the various spectral data viz., IR, 1HNMR, Mass and elemental analysis. The structure of acid was assigned on the basis of their IR spectrum which shows a very broad band at 3200-2500 cm-1 attributable to the stretching of carboxylic OH group. Fragmentation pattern was also studied which gave different fragment with their corresponding mass to charge ratio. The synthesized compounds are under investigation for their insulinotropic activities.