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.
X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
Ultrason Sonochem. 2020 Nov;68:105222. doi: 10.1016/j.ultsonch.2020.105222. Epub 2020 Jun 15.
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/NaPO as a Cl source, oxidant and/or catalyst under ultrasonic irradiation in EtOH/HO (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.
一种从 N-烯丙基-5-亚苄基噻唑烷-2,4-二酮 3 作为双烯和亲偶极体与芳基腈氧化物通过 1,3-偶极环加成反应合成新型 N-噻唑烷-2,4-二酮异恶唑啉衍生物 5 的快速绿色方法。相应的 N-烯丙基取代双烯和亲偶极体通过一锅法从噻唑烷-2,4-二酮与醛在 Knoevenagel 缩合反应后，在超声下于 NaOH 水溶液中进行 N-烯丙基化反应制备。此外，异恶唑啉衍生物 5 通过在超声辐射下使用廉价温和的 NaCl/Oxone/NaPO 作为 Cl 源、氧化剂和/或催化剂，在 EtOH/HO（v/v，2:1）中作为绿色溶剂进行区域选择性和化学选择性 1,3-偶极环加成反应合成。所有合成产物都在短反应时间内以良好的收率提供，然后通过 NMR、质谱和 X 射线晶体学分析确认其结构。
