Selective silver (I)-catalyzed four-component gram-scale synthesis of novel 1,4-disubstituted 1,2,3-triazole-sulfonamides under heterogeneous catalysis and microwave irradiation in water

• Published in: Results in Chemistry 2022-01, Vol.4, p.100552, Article 100552
• Main Authors: El Mahmoudi, Ayoub, El Masaoudi, Hind, Tachallait, Hamza, Talha, Aicha, Arshad, Suhana, Benhida, Rachid, Jaber, Boujemaâ, Benaissa, Mohammed, Bougrin, Khalid
• Format: Article
• Language: English
• Subjects: 1,2,3-Triazole-sulfonamide; Gram-scale; Green process; Heterogeneous catalysis; Multi-component; Selective AgAAC reaction; Silver Phosphate catalyst
• ISSN: 2211-7156; 2211-7156
• DOI: 10.1016/j.rechem.2022.100552

•Four-Component Ag(I)-catalyzed Synthesis of 1,2,3-Triazole-sulfonamides under MW.•Regioselective synthesis of 1,2,3-triazoles, using silver in water.•Highly active, selective and reusable catalyst system (Ag3PO4-MEA)•Green, sustainable and low-cost reagents, catalyst and solvents.•Novel products were prepared with good yields and shorter reaction times. The Ag3PO4-MEA catalyst was successfully prepared and proved to be an efficient and selective catalyst of the multicomponent synthesis of a new library of 1,4-disubstituted 1,2,3-triazole-sulfonamides 5a-n. This new methodology cleanly proceeded in water under microwave activation using N-propargyl saccharin, NaN3 or SO2(N3)2, substituted benzyl chloride or protected sugar and non-conjugated primary amines, using Ag(I) in a method-comparison study to Cu(I) as conventional Sharpless catalyst. The proposed strategy allows a simple, rapid and scalable route to 1,2,3-triazoles sulfonamides derivatives 5 through in-situ ring-opening of saccharin system with primary amine. All compounds have been fully characterized by NMR, mass spectrometry and X-ray crystallography analysis. The catalyst has been prepared via a green Sol-Gel methodology and fully analyzed by X-ray Diffraction (XRD), Fourier Transform Infrared (FTIR) Spectroscopy and Scanning Electron Microscopy (SEM) coupled to Energy Dispersive X-ray Spectroscopy (EDX), and Brunauer-Emmett-Teller (BET) method. The catalyst is easily recovered during the process and showed high recyclability.