Synthesis and characterization of new biocatalyst based on LDH functionalized with l-asparagine amino acid for the synthesis of tri-substituted derivatives of 2, 4, 5-(H1)-imidazoles

Shahram Moradi; Hadi Hassani Ardeshiri; Alireza Gholami; Hossein Ghafuri

doi:10.1016/j.heliyon.2023.e22185

Synthesis and characterization of new biocatalyst based on LDH functionalized with l-asparagine amino acid for the synthesis of tri-substituted derivatives of 2, 4, 5-(H1)-imidazoles

Heliyon. 2023 Nov 11;9(11):e22185. doi: 10.1016/j.heliyon.2023.e22185. eCollection 2023 Nov.

Authors

Shahram Moradi¹, Hadi Hassani Ardeshiri¹, Alireza Gholami¹, Hossein Ghafuri¹

Affiliation

¹ Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran.

Abstract

In this study, a new and recyclable biocatalyst (MgAl CO₃-LDH@Asn) was synthesized by immobilizing l-asparagine amino acid (Asn) on the surface of 3-(chloropropyl)-trimethoxysilane modified MgAl CO₃-layered double hydroxide (LDH). The physicochemical properties of the samples were identified by Fourier transform infrared (FT-IR), X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), and thermogravimetric analysis (TGA) techniques. The MgAl CO₃-LDH@Asn was employed in the multi-component assembly process for the synthesis of tri-substituted derivatives of 2,4,5-(H1)-imidazoles from benzyl, various benzaldehyde derivatives, and ammonium acetate. For optimizing the reaction, the main factors, including the amount of MgAl CO₃-LDH@Asn, type of solvent, reaction time, and temperature were evaluated. The optimum conditions of the model reaction were achieved using 20 mg of MgAl CO₃-LDH@Asn biocatalyst in ethanol solvent after 20 min at reflux temperature. According to the findings above, the results indicated that high-yield products are achieved within a short time frame. Moreover, the high catalytic activity of the MgAl CO₃-LDH@Asn was maintained for four cycles without significantly diminishing its performance.

Keywords: Asparagine; Biocatalyst; Imidazole; Layered double hydroxide; Multi-component assembly.