Efficient combination of task-specific ionic liquid and microwave dielectric heating applied to one-pot three component synthesis of a small library of 4-thiazolidinones |
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Authors: | Joan Fraga-DubreuilJean Pierre Bazureau |
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Affiliation: | Institut de Chimie, Synthèse & Electrosynthèse Organiques 3, Université de Rennes 1, UMR 6510, Bât. 10A, Campus de Beaulieu, CS 74205, (F) 35042 Rennes Cedex, France |
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Abstract: | The first report of the use of task-specific ionic liquid as synthetic equivalent of ionic liquid-phase matrice for the preparation of a small library of 4-thiazolidinones is reported in this paper. The starting (ethyleneglycol)ionic liquid-phase is functionalized in good yields with 4-(formylphenoxy)butyric acid by using usual esterification reaction conditions (DCC/DMAP as catalyst). The synthesis of the ionic liquid-phase bound 4-thiazolidinones was performed by a one-pot three-component condensation under microwave dielectric heating. The final cleavage under microwave/catalysis strategy provides the expected 4-thiazolidinones in high purity after flash-chromatography purification. According to the ionic liquid-phase organic synthesis (IoLiPOS) methodology, it was found that optimized reaction conditions were performed by standard analytical methods (NMR, TLC). The 1H, 13C NMR spectrum of some representative 4-thiazolidinones and ionic liquid-phase bound benzaldehyde are also reported. |
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Keywords: | ionic liquid microwave 4-thiazolidinone task-specific ionic liquid three-component condensation |
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