DBSA catalyzed, one-pot three-component “on water” green protocol for the synthesis of 2,3-disubstituted 4-thiazolidinones

Abstract

A simple and environmentally benign one-pot three-component tandem synthesis of a series of novel 4-thiazolidinones has been accomplished ''on water'' by reacting aliphatic or aromatic primary amines with thioglycolic acid and a wide range of aromatic aldehydes at ambient temperature using p-dodecylbenzenesulfonic acid (DBSA) as a Brønsted acid-surfactant combined catalyst. The unique ability of the catalyst has been utilised to form emulsion droplets with organic substrates in aqueous medium whose interior core is hydrophobic enough to exclude the water molecules generated during the rate limiting dehydration step of the reaction. This protocol worked well with a variety of substrates and the desired products were obtained in fairly good yields.

One-pot rapid synthesis of thiazole-substituted pyrazolyl-4-thiazolidinones mediated by diisopropylethylammonium acetate

“…Aromatic amines having halide groups reacted smoothly, and the products were obtained in excellent yields ranging from 79 to 88 % ( Table 5, entries [3][4][5][8][9][10]. Slightly moderate yields of the product were obtained when heterocyclic aldehydes were allowed to react with aromatic amines having electron-donating group such as CH 3 (Table 5, entries 2, 7).…”

“…It is generally believed that the last step, i.e. removal of the water molecule, is rate determining and seems to be critical for obtaining 4-thiazolidinones in high yield [4]. Therefore, a number of strategies have been developed to remove the water molecules formed during the reaction in order to obtain high yield of the desired product.…”

“…Electron-donating group such as OCH 3 , CH 3 and OH present in the aldehyde afforded moderate yields of the products (Table 4, entries[4][5][6][7][8][9][10][11][12]. Presence of Cl group in the aldehydes (Table 4, entries 13-15) showed good effect on yield.…”

An Efficient Method for the Synthesis of N‐uracil‐4‐oxo‐thiazolidines without Catalyst

“…The most well‐known and classical method for the synthesis of these compounds includes two‐component and three‐component reactions involving primary amines, an oxo‐compound and thiolic acids in the presence of diverse catalysts, such as hexafluorophosphate benzotriazole tetramethyl uronium , N , N ′‐dicyclohexylcarbodiimide , silica gel , [bmim][PF 6 ] , ZnCl 2 , ferrite , Hunig's base , [BmIm]OH , molecular sieves , sodium sulfate , montmorillonite K‐10 , nano‐Fe 3 O 4 @SiO 2 , [Et 3 NH][HSO 4 ] , DBSA , and baker's yeast .…”

Utilisation of Home Laundry Effluent (HLE) as a catalyst for expeditious one-pot aqueous phase synthesis of highly functionalised 4-thiazolidinones

“…More recently, commercially available surfactant p -dodecylbenzenesulfonic acid (DBSA) has been reported for synthesis of 2,3-di substituted 4-thiazolidinones derivatives (Prasad et al 2012). Thus, there has been an urgent need to develop a benign, eco-friendly and inexpensive protocol for the synthesis of 4-thiazolidinone derivatives.…”