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

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  1 , Hadi Hassani Ardeshiri  1 , Alireza Gholami  1 , Hossein Ghafuri  1
Affiliations

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 et al. Heliyon. .

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.

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Conflict of interest statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Figures

Scheme 1
Scheme 1
Preparation process of the MgAl CO3-LDH-CPTMS@Asn nanocomposite.
Scheme 2
Scheme 2
Synthesis of tri-substituted derivatives of 2, 4, 5-(H1)-imidazoles (4a-l) catalyzed with MgAl CO3-LDH@Asn biocatalyst through the three-component reaction between benzyl (1 mmol), benzaldehyde (1 mmol), ammonium acetate (5 mmol) in EtOH solvent at reflux temperature.
Fig. 1
Fig. 1
FT-IR spectra of (a) MgAl CO3-LDH and (b) MgAl CO3-LDH@Asn biocatalyst.
Fig. 2
Fig. 2
XRD pattern of MgAl CO3-LDH@Asn biocatalyst.
Fig. 3
Fig. 3
SEM images of (a,b) Mg–Al LDH, (c,d,e) MgAl CO3-LDH@Asn biocatalyst, and (f) histogram diagram of the MgAl CO3-LDH@Asn.
Fig. 4
Fig. 4
EDX analysis of MgAl CO3-LDH@Asn biocatalyst.
Fig. 5
Fig. 5
TGA curve of the MgAl CO3-LDH@Asn biocatalyst.
Scheme 3
Scheme 3
The suggested reaction mechanism for the synthesizing of tri-substituted derivatives of 2, 4, 5-(H1)-imidazoles in the presence of MgAl CO3-LDH@Asn biocatalyst.
Fig. 6
Fig. 6
Reusability efficiency of MgAl CO3-LDH@Asn biocatalyst for the synthesis of tri-substituted derivatives of 2, 4, 5-(H1)-imidazoles after first, second, third, and fourth recyclability.
See this image and copyright information in PMC

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