Background: Thiazolidinone and pyrazoles are promising heterocyclic systems enormously contributing
to medicinal chemistry and when pyrazole nucleus was incorporated in other biodynamic heterocycles,
the resulting molecules have displayed an increased spectrum of biological activities. There are
several synthetic routes for the synthesis of thiazolidinone molecules but are having certain lacunas
like, need of catalysts and desiccants, higher reaction temperature, longer reaction time, organic solvents
and tedious work up procedure.
Methods: Here an ultrasound promoted one pot multicomponent protocol is developed for 2-[(1-phenyl-3-(substituted
phenyl) -pyrazol-4-yl)] methylene hydrazolyl-4-thiazolidinones (6a-g). Here freshly prepared substrates, 3-(4-substituted
phenyl)-1-phenyl-1H-pyrazole-4-carbaldehydes (5a-g), have been condensed with thiosemicarbazide (2) and ethylbromo
acetate (3) in aqueous emulsion of surfactant, CTAB under ultrasonication.
Results: In our study the titled compounds 2-[(1-phenyl-3-(substituted phenyl) -pyrazol-4-yl)] methylene hydrazolyl-4-
thiazolidinones obtained with good to excellent yields using 20 mol% aqueous emulsion of CTAB under ultrasound irradiation
Conclusion: First time we have provided an environmentally friendly ultrasound promoted synthetic route to 2-
hydrazolyl-4-thiazolidinones (4a-g) and biologically significant 2-[(1-phenyl-3-(substituted phenyl) -pyrazol-4-yl)] methylene
hydrazolyl-4-thiazolidinones (6a-g) using aqueous emulsion of CTAB as reaction medium. The method offered
several advantages such as operational simplicity, easy work-up procedure, shorter reaction times and high yields. The
protocol is safe, economic and convenient for obtaining library of 2-hydrazolyl/imino-4-thiazolidinones rapidly.