Compounds containing the 1,3-thiazolidine-2,4-dione scaffold are gaining increasing scientific interest as potential interventional agents for a variety of disease states. A four-step synthesis of ethyl-(2-(5-arylidine-2,4dioxothiazolidin-3-yl)acetyl)glycinates, alaninates, butanoates, valinates and norvalinates is described. The synthesis began by converting 1,3-thiazolidine-2,4-dione into its potassium salt, which was treated with ethyl (2-chloroacetamido)glycinates, alaninates, butanoates, valinates and norvalinates, respectively, to obtain the penultimate products. These products were then subjected to a Knoevenagel condensation reaction with different aldehydes to obtain the desired products in low to excellent yields.
Compounds containing a hydantoin moiety are found in several medicines in clinical use. In this research, ethyl- and methyl-[2-(5-benzylidene)-2,4-dioxoimidazolidin-3-yl]acetyl esters are successfully synthesized over four reaction steps using conventional methods. The synthesis begins by subjecting hydantoin to a Knoevenagel condensation reaction with three different benzaldehydes to afford the penultimate products, which are further reacted with ethyl or methyl (bromoacetyl)alaninates, butanoates, valinates, and norvalinates to give the desired products as esters in low to moderate yields.
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