Preparation of nanodiamond anchored on copper tannic acid as a heterogenous catalyst for synthesis of 1,4-benzodiazepines derivatives

Reza Ghalavand; Hossein Ghafuri; Hadi Hassani Ardeshiri

doi:10.1038/s41598-024-58563-0

Preparation of nanodiamond anchored on copper tannic acid as a heterogenous catalyst for synthesis of 1,4-benzodiazepines derivatives

Sci Rep. 2024 Apr 15;14(1):8655. doi: 10.1038/s41598-024-58563-0.

Authors

Reza Ghalavand¹, Hossein Ghafuri², Hadi Hassani Ardeshiri¹

Affiliations

¹ Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran.
² Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran. ghafuri@iust.ac.ir.

Abstract

In this research, a new and eco-friendly heterogeneous catalyst (ND@Tannicacid-Cu) was synthesized based on nanodiamond and copper tannic acid via esterification process. The as-prepared catalyst was characterized by Fourier transforms infrared spectroscopy (FT-IR), energy dispersive X-ray spectroscopy (EDX), scanning electron microscopy (SEM), and X-ray diffraction (XRD) methods. The catalytic efficacy of the intended catalyst was examined by one-step three-component reaction of 1,4-benzodiazepine derivatives from a mixture of ortho-phenylenediamine, aromatic aldehydes, and dimedone under mild conditions. In all instances, corresponding 2,4-benzodiazepines derivatives were synthesized with high efficiency, short reaction time, straightforward work up procedure, no requirement for column-chromatography, and cost-effective catalyst. The heterogeneous catalyst was easily recycled using fillers, and it can be reused for eight cycles without significantly diminishing its performance.

Keywords: Benzodiazepine; Esterification process; Heterogeneous catalyst; Nanodiamond; Tannic acid.