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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Output type: Journal article

UM6P affiliated Publication?: Yes

Author list: Thari, Fatima Zahra; Tachallait, Hamza; El Alaoui, Nour-Eddine; Talha, Aicha; Arshad, Suhana; Alvarez, Eleuterio; Karrouchi, Khalid; Bougrin, Khalid

Publisher: Elsevier

Publication year: 2020

Journal: Ultrasonics Sonochemistry (1350-4177)

Volume number: 68

ISSN: 1350-4177

Languages: English (EN-GB)


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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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Last updated on 2021-13-06 at 23:17