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4-Thiazolidinones are one of the emerging classes of heterocyclic privileged scaffold. Because of their biological importance, several methods have been developed for the synthesis of 4-thiazolidinone skeleton. The only method reported for solid phase synthesis of 4-thiazolidinones is by C. P. Holmes. A careful survey of the literature revealed that solid-phase synthesis of 4-thiazolidinone with a suitable methodology has not been reported yet. The challenge is to develop a solid phase methodology that affords fast and easy generation of combinatorial library of 4-thiazolidinones, with high yield and appropriate diversity. There are three major points for diversification in 4-thiazolidinone scaffold pointed out providing an opportunity to explore different substituent at these positions. Therefore, the present study makes an effort towards the synthesis of a library of 4-thiazolidinones and 4-metathiazanones with suitable diversity at one, two or three points with the use of suitable coupling agents and other reagents.