Alum [KAl(SO4)2•12H2O] catalyzed microwave assisted synthesis of 5-arylidine-2-(methylthio)-thiazolone derivatives in water

Abstract

An efficient and environmentally benign method has been developed for the synthesis of 5arylidine-2-(methylthio)-thiazolones derivatives using Alum [KAl(SO4)2•12H2O] catalyst and triethyl amine in water under microwave irradiation. This green transformation generated one C-S and one CC bond, condensation and S-methylation. Notable advantages for the present protocol include, short reaction time, cleaner reaction profile and easy isolation of product by microwave irradiation technique using green catalyst and solvent.

Design of a new multi-functional catalytic system Ni/SO3H@zeolite-Y for three-component synthesis ofN-benzo-imidazo- or -thiazole-1,3-thiazolidinones

“…The classical synthesis reported can be either a one-pot or a twostep process through condensation of amines and aromatic aldehydes, and thioglycolic acid. Although various heterogeneous and homogenous catalysts have been applied for the substituted 1,3-thiazolidin-4-ones, [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] synthesis of new thiazolidine heterocycles and exploration for greener and cleaner synthetic strategies still remains as an active research.…”

4‐Hydroxycoumarin: A Versatile Substrate for Transition‐metal‐free Multicomponent Synthesis of Bioactive Heterocycles

“…[59] Another alternative approach for the synthesis of a vast array of pyrazolyl-coumarin derivatives 49 has been established by Jadhav and Shloorkar in the same year (Scheme 11c). [60] By using 10 mol% of alum [KAl(SO 4 ) 2 • 12H 2 O] as the transitionmetal-free catalyst, the desired products 49 derived from the multicomponent reaction of 4-hydroxycoumarin 1, aldehydes 31, hydrazines 47, and ethyl acetoacetate 48 under microwave irradiation, has been obtained in 70-97% yield. Not only the aryl aldehydes but also heteroaryl and alkyl aldehydes were well tolerated by this methodology.…”

Synthesis, biological evaluation, and molecular docking study of thiophene‐, piperazine‐, and thiazolidinone‐based hybrids as potential antimicrobial agents

“…Pansare et al [27] described the synthesis of 2‐((4‐oxo‐5‐(thiophen‐2‐ylmethylene)‐4,5‐dihydrothiazol‐2‐yl)amino)‐substituted acids, which were then used to generate effective antibacterial drugs. Jadhav et al [28], on the other hand, synthesized 5‐arylidine‐2‐(methylthio)‐thiazolone derivatives as a key precursor in the synthesis of antibacterial drugs. Kalaria et al [29] prepared several thiazol‐4(5 H )‐one derivatives, including 2‐(5′‐(1 H ‐benzo[ d ]imidazol‐1‐yl)‐3′‐methyl‐1′‐phenyl‐5‐(thiophen‐2‐yl)‐3,4‐dihydro‐1′ H , 2 H ‐[3,4′‐bipyrazol]‐2‐yl)‐5‐(thiophen‐2‐ylmethylene)thiazol‐4(5 H )‐one, which was found to be the most effective compound against E. coli with the IC 50 value 9.1 μM.…”