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
Ayoub El Mahmoudi, Hind El Masaoudi, Hamza Tachallait, Aicha Talha, Suhana Arshad, Rachid Benhida, B. Jaber, Mohammed Benaïssa, Khalid Bougrin
Abstract
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.