One-pot four-component tandem synthesis of novel sulfonamide-1, 2, 3-triazoles catalyzed by reusable copper (II)-adsorbed on mesoporous silica under ultrasound irradiation. (18th June 2021)

• Record Type: Journal Article
• Authors: Talha, Aicha; Mourhly, Asmae; Tachallait, Hamza; Driowya, Mohsine; El Hamidi, Adnane; Arshad, Suhana; Karrouchi, Khalid; Arsalane, Said; Bougrin, Khalid
• Is Part Of: Tetrahedron. Volume 90(2021)
• Publication Date: 2021-06-18
• Subjects: Ultrasound -- Four-component tandem -- One-pot -- 1, 3-dipolar cycloaddition -- 1, 2, 3-triazoles -- Sulfonamide -- mSiO2-Cu (II); Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132215
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A green and efficient synthesis of new sulfonamide-1, 2, 3-triazoles 5 in heterogeneous conditions has been developed. The procedure involved one-pot four-component tandem sulfonamidation/azidation/1, 3-dipolar cycloaddition (1, 3-DC ) reactions under a cooperative effect of ultrasound irradiation and Cu (II) supported on amorphous mesoporous silica [mSiO2 -Cu (II)] catalysis at room temperature in aqueous medium. In addition, the 1, 4-disubstituted 1, 2, 3-triazoles 5 were synthesized by regioselective and chemoselective methods to afford the pure products in excellent yields and short reaction times under ultrasonic irradiation. The supported catalyst has been prepared from copper (II) nitrate by simple method using ultrasound activation and characterized by X-ray diffraction (XRD), Brunauer-Emmett-Teller (BET) method and Barrett-Joyner-Halenda (BJH) method. Also, the catalyst is easily prepared, stable, efficient, selective, and reusable under ultrasonic conditions. Graphical abstract: Image 1 Highlights: Ultrasound-assisted four-component one-pot synthesis of novel sulfonamides-1, 2, 3-triazoles. Regioselective synthesis of 1, 2, 3-triazoles, using Cu (II)-adsorbed on mesoporous silica [mSiO2-Cu(II) ] in aqueous media. Highly active, selective and reusable catalyst system [mSiO2 -Cu(II)]. Green and inexpensive reagents, and low-cost catalyst and solvents. Novel products were prepared with good yields in shorter times, the compound 5c is isolated a single regioisomeric form.