Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water

Abstract

In the present work, we have designed a novel, heterogeneous and recyclable magnetic Brønsted acidic ionic liquid based on 5-phenyl-1H-tetrazole. The {Fe₃O₄@SiO₂@(CH₂)₃5-phenyl-1H-tetrazole-SO₃H/Cl} ([FSTet-SO₃H]Cl) was prepared via the immobilization of 5-phenyl-1H-tetrazole-bonded sulfonic acid onto the surface of silica-coated magnetic nanoparticles using 3-chloropropyltriethoxysilane as a linker. The catalyst was characterized by XRD, TEM, FESEM, EDS, TG-DTA, and FT-IR. The ability and high activity of this catalyst were demonstrated in the synthesis of 1-carbamoyl-1-phenylureas with good to excellent yields via a new, simple and one-pot procedure in aqueous media under reflux conditions. This procedure has advantages such as high yields, short reaction times, a simple methodology and work-up process, green reaction conditions, high stability, catalytic activity, and easy preparation, separation and reusability of the catalyst. The synthesis of these compounds was confirmed by FT-IR, ¹H NMR, ¹³C NMR and CHN. In addition, we investigated the biological properties of the 1-carbamoyl-1-phenylureas as newly synthesized compounds. The described catalyst could be easily separated from the reaction mixture by additional magnetic force and reused several times without a remarkable loss of its catalytic activity and any considerable changes in the product yield and the reaction time.