Graphene oxide-THEIC-ECH-Chitosan network nanocomposite: a novel, efficient and recyclable catalyst for green synthesis of polyhydroquinoline derivatives

Mohammad Dekamin,Ehsan Valiey,Negin Rostami,Reza Mohamadiani,Mohammad Eslami

doi:10.3390/ecsoc-24-08456

Abstract

In this present research, two linkers have been utilized for the covalent attachment of graphene oxide with chitosan. Graphene oxide (GO) and chitosan (Cs) were crosslinked by using 1,3,5-tris(2-hydroxyethyl) isocyanurate (THEIC) and epichlorohydrin (ECH) which resulted in forming the expected biopolymer network nanocomposite. The obtained network was characterized by Fourier transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM), X-ray diffraction (XRD), energy dispersive X-ray spectroscopy (EDS) and thermal gravimetric analysis (TGA) technique. The catalytic application of the GO-THEIC-ECH-Cs nanocatalyst was then investigated in one-pot four-component Hantzsch condensation reaction for the synthesis of polyhydroquinoline derivatives in EtOH under reflux conditions. The obtained results indicated that the applied catalyst in this study exhibited some the significant advantages such as reusability and highly efficiency, stability, low required loading, avoiding the use of toxic transition metals, short reaction times, higher yields, easy separation and purification of the products.

Highlights

Multicomponent reactions (MCRs) have emerged as important organic synthesis approaches which involve reactions of three or more reactants come together in a single reaction vessel to form new products that have portions of all the components
The reaction between 1.0 mmol dimedone, 1.0 mmol aryl aldehyde, 1.0 mmol ethyl acetoacetate, 2.0 mmol ammonium acetate and 1.0 mg of Graphene oxide (GO)-tris(2-hydroxyethyl) isocyanurate (THEIC)-ECH-Cs nanocatalyst in 5 mL of EtOH under refluxing conditions was performed for the synthesis of polyhydroquinoline derivatives
The catalytic activity of GO-THEIC-ECH-Cs (1) was evaluated in the green synthesis of polyhydroquinoline derivatives by condensing dimedone, aryl aldehyde derivatives, ethyl acetoacetate and ammonium acetate in EtOH at reflux temperature

Summary

Introduction

Multicomponent reactions (MCRs) have emerged as important organic synthesis approaches which involve reactions of three or more reactants come together in a single reaction vessel to form new products that have portions of all the components. MCRs strategies grant remarkable advantages over conventional bimolecular reactions owing to their convergence, atom-economy, operational simplicity, structural diversity and short synthetic pathway. MCRs have recently gained a new dimension in the field of designing methods to produce elaborate biologically active compounds and new molecular frameworks for potential drugs with diverse pharmacological activities [1,10,16]. We are living in an era in which everything is becoming smaller and smaller in size with improvements in properties. Using these composites especially in organic reactions appears to be essential and important. For comprehending the importance of the issue, we have introduced a green nanocomposite that has valuable properties such as thermal stability, mechanical strength and a wide surface

Methods

Results

Conclusion