Highly Efficient and Chemoselective Synthetic Route to de Thiazolidinones via a Microwave Assisted, Three Component Reaction

Romina Ocampo,Liliana Koll,Mirta Fascio,Norma D'Accorso

doi:10.3390/ecsoc-18-c002

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.

Highlights

Microwave irradiation is an alternative heating method based on the ability of some compounds to transform electromagnetic energy into heat
We present here the study of selective synthesis of 1,3-thiazolidin-4-ones via microwave-assisted multi-component reaction under solvent-free conditions
Microwave irradiation reactions has been extended to almost all areas of chemistry with the exception of the carbohydrate chemistry which has suffered a certain delay, as it is testified by the small number of applications

Summary

Introduction

Microwave irradiation is an alternative heating method based on the ability of some compounds to transform electromagnetic energy into heat. Theoretically two different products are possible (benzothiazepinones 4 and thiazolidinones 5), the reaction gave only two diasteroisomers of 1,3-thiazolidin-4-ones (48-97%) in the threecomponent reaction between 2,3 : 4,5-di-O-isopropiliden-β-D-arabino-hexos-2-ulo-2,6piranosa 1, different heteroaromatics anilines 3 and mercaptoacetic acid 2 as can be seen in the scheme of Figure 1. 4-thiazolidinones (5) have been synthesized by one pot microwave-assisted multicomponent reaction, under solvent-free condition, of 2,3:4,5-di-Oisopropylidene- -D-arabino-hexos-2-ulo-2,6-pyranose (1), mercaptoacetic acid (2) and various heteroaromatic amines (3) (Figure 1).

Results

Conclusion