Chitosan/CuO nanocomposite films mediated regioselective synthesis of 1,3,4-trisubstituted pyrazoles under microwave irradiation

Abstract

Copper oxide-chitosan nanocomposite was synthesized simply via simple solution casting method and was characterized by different analytical techniques, including Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), Field emission scanning electron microscopy (FESEM), and Thermogravimetric analysis (TGA). The copper oxide content in the prepared nanocomposite film was estimated from the Energy-dispersive X-ray spectroscopy (EDS) and the copper content in the sample was found to be 12.57 wt%. From the XRD pattern, the average particle size was calculated using Debye-Scherrer formula and was found to be 33.5 nm. The TGA curves showed that the thermal stability of the hybrid nanocomposite was found to be superior to the native CS, which is attributed to the existence of the thermally stable CuO. The chitosan/CuO nanocomposite has proven to be an excellent heterogeneous base catalyst for regioselective 1,3-dipolar cycloaddition of hydrazonoyl chlorides 1a-j with enamine 2 to give 1,3,4-trisubstituted pyrazoles 3a-j in excellent yields. The performance of the nanocomposite was optimized by varying several reaction conditions.

Keywords

• Chitosan
• Copper oxide nanoparticles
• Hydrazonoyl chlorides
• Enamine
• 1,3-Dipolar cycloaddition