Cu/TCH-pr@SBA-15 nano-composite: A new organometallic catalyst for facile three-component synthesis of 4-arylidene-isoxazolidinones

Abstract

A copper complex supported on SBA-15 nanoparticles (Cu/TCH-pr@SBA-15) was synthesized by the post-synthesis modification of nano-mesoporous silica with 3-chloropropyltriethoxysilane (CPTES) and thiocarbohydrazide (TCH) and subsequent metal-ligand coordination with Cu(ii). These nanocomposites were thoroughly characterized by FT-IR spectroscopy, TEM, FE-SEM, EDX, atomic absorption spectroscopy and N2 adsorption-desorption (BET) studies. Then, a solvent-free method was developed for the three-component synthesis of 4-arylidene-isoxazolidinones via condensation of hydroxylamine hydrochloride, ethyl acetoacetate and various aromatic aldehydes using Cu/TCH-pr@SBA-15 as a highly efficient nanocatalyst. This new economic and eco-friendly methodology has remarkable advantages such as excellent yields, a shorter reaction time, an easy purification procedure, simplicity, green conditions, solvent-free conditions, and recoverability of the nanocatalyst.