Highly efficient and chemoselective synthetic route to thiazolidinones via a microwave assisted, three component reaction

ROMINA A. OCAMPO; LILIANA C. KOLL; MIRTA FASCIO; SANDRA D. MANDOLESI; NORMA B. D?ACCORSO

web - electronic conference

Conferencia; ECSOC-18 (18th International Electronic Conference on Synthetic Organic Chemistry); 2014

MDPI

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 gave 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 as can be seen in the scheme of Figure 1. The synthesized compounds were characterized by IR, 1H-, 13C, DEPT and HSQC - RMN. The stereochemistry of both the diasteroisomers was elucidated with the help of NOE experiments.