Ultrasound-assisted one-pot green synthesis of new N- substituted-5-arylidene-thiazolidine-2,4-dione-isoxazoline derivatives using NaCl/Oxone/Na3PO4 in aqueous media |
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| Affiliation: | 1. Equipe de Chimie des Plantes et de Synthèse Organique et Bioorganique, URAC23, Faculty of Science, B.P. 1014, Geophysics, Natural Patrimony and Green Chemistry (GEOPAC) Research Center, Mohammed V University of Rabat, Morocco;2. X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia;3. Instituto de Investigaciones Químicas, CSIC–Universidad de Sevilla, Avda. Américo Vespucio 49, 41092 Sevilla, Spain;4. Laboratory of Analytical Chemistry and Bromatology, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco;5. Mohammed VI Polytechnic University, Lot 660, Hay Moulay Rachid, Benguerir, Morocco |
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| Abstract: | A rapid and green method for the synthesis of novel N-thiazolidine-2,4-dione isoxazoline derivatives 5 from N-allyl-5-arylidenethiazolidine-2,4-diones 3 as dipolarophiles with arylnitrile oxides via 1,3-dipolar cycloaddition reaction. The corresponding N-allyl substituted dipolarophiles were prepared by one-pot method from thiazolidine-2,4-dione with aldehydes using Knoevenagel condensation followed by N-allylation of thiazolidine-2,4-dione in NaOH aqueous solution under sonication. In addition, the isoxazoline derivatives 5 were synthesized by regioselective and chemoselective 1,3-dipolar cycloaddition using inexpensive and mild NaCl/Oxone/Na3PO4 as a Cl source, oxidant and/or catalyst under ultrasonic irradiation in EtOH/H2O (v/v, 2:1) as green solvent. All synthesized products are furnished in good yields in the short reaction time, and then their structures were confirmed by NMR, mass spectrometry and X-ray crystallography analysis. |
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| Keywords: | Ultrasound Thiazolidine-2,4-dione Isoxazoline 1,3-dipolar cycloaddition One-pot Green chemistry |
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