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Highly Efficient and Chemoselective Synthetic Route to de Thiazolidinones via a Microwave Assisted, Three Component Reaction
Published: 31 October 2014 by MDPI in The 18th International Electronic Conference on Synthetic Organic Chemistry session Microwave Assisted Synthesis
Abstract: The thiazolidinones and correlated motifs have high biological relevance since they are present in both natural products and pharmaceutical compounds.Microwave irradiation is an alternative heating method based on the ability of some compounds to transform electromagnetic energy into heat. This method, which increases chemical reaction rates and forms cleaner products, can be successfully applied in pharmaceutical chemistry.We present here the study of selective synthesis of 1,3-thiazolidin-4-ones via microwave-assisted multi-component reaction under solvent-free conditions. Although, theoretically two different products are possible (benzothiazepinones 4 and thiazolidinones 5), the reaction yielded only two diasteroisomers of 1,3-thiazolidin-4-ones (48-97%)in the three-component reaction between 2,3 : 4,5-di-O-isopropiliden-β-D-arabino-hexos-2-ulo-2,6-piranosa 1, different heteroaromatics anilines 3 and mercaptoacetic acid 2 (Scheme 1). The synthesized compounds were characterized by IR, 1H-, 13C y DEPT and HSQC - RMN. The stereochemistry of both the diasteroisomers was elucidated with the help of NOE experiments.
Keywords: Thiazolidinones; chemoselective synthesis; multicomponent reaction