Trietheylamine Catalyzed One- Pot Solvent-Free Synthesis Of 3-Alkyl-5-((5- (Chloromethyl)Furan-2-yl)methylene)-2-Thioxothiazolidine-4-One

Rhodanines, thiazolidinediones, and related heterocycles have been discussed extensively and controversially as key structures in medicinal chemistry [1]. Rhodanines are known to have biological activities, such as anti-diabetic, anti-inflammatory, anti-oxidant, anti-tubercular, anti-microbial, anti-convulsant and cytotoxic activities [2]. Rhodanine derivatives with the exocylic double bond at position five are the most commonly synthesized rhodanine derivatives. 5-Arylmethylidenerhodanines usually synthesized by base-catalyzed Knoevenagel condensation between rhodanines or N-substituted rhodanines and aromatic aldehydes, using either conventional or microwave heating [3]. 5-(Chloromethyl)furfural (CMF) is newable platform molecule which can be derived in a single step from sugars, cellulose, or raw biomass [4]. In this paper we wish to report a simple one-pot solvent-free procedure to prepare 3-alkyl-5-((5- (chloromethyl)furan-2-yl)methylene)-2- thioxothiazolidine-4-ones via the reaction of primary amines, carbon disulfide, and bromoethylacetate and CMF in the presence of a catalytic amount of triethylamine (Scheme 1). The structure of the synthesized compounds were fully confirmed by spectroscopic (IR, 1HNMR, 13C NMR, and Mass) analysis.