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

Abstract

Abstract: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,

<strong>Study of the effect of solvent and different Lewis acids in one pot multicomponent microwave assisted reaction for the chemoselective generation of </strong><strong>1.4-thiazepan-3-ones and 4-tiazolidinones.</strong>

“…Based on the previous studies of our research group, we could established that the tricomponent microwave assisted reaction between 2,3:4,5-di-O-isopropylidene--D-arabino-hexos-2-ulo-2,6-pyranose (1), mercaptoacetic acid (2) and various heteroaromatic amines (3), without solvent (Method A), proved to be a simple eco-friendly method because of the atoms economy, reaction time, high yields and low cost economic starting products for the synthesis of the corresponding 4-thiazolidinones (5) as the only products and as diastereomeric mixtures [4,5]. On the other side, when stoichiometric amounts of the boronic ester A (dimethyl-(4S,5S)-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate) was added together with the reactants 1, 2 and 3, not only selective formation of diastereomers from 1,4-thiazepan-3-one (4) was observed but also an increase in the proportion of one of them (Figure 1) [6,7].…”