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Current Organic Synthesis

Author(s): Marzieh Janani, Masumeh Abdoli Senejani* and Tahereh Momeni Isfahani

DOI: 10.2174/1570179417666200117110758

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An Efficient Synthesis of Benzimidazole and Benzothiazole Derivatives Using a Nickel(II) Metal-Organic Framework

Page: [109 - 116] Pages: 8

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Abstract

Background: The benzimidazoles and benzothiazoles have shown relatively high pharmaceutical and biological activities. In recent years, numerous methods have been developed for synthesis of benzimidazole and benzothiazole derivatives using different catalysts. However, only some of the reported procedures are quite satisfactory and most of them have drawbacks. Herein, we report a convenient method for synthesis of benzimidazole and benzothiazole derivatives using a nickel (II) metal-organic framework (Ni- MOF) as a novel and reusable catalyst. The presence of unsaturated metal centers makes metal-organic frameworks to be used as Lewis acid catalysts.

Objective: The primary objective of this study was to describe an efficient method for synthesis of benzimidazole and benzothiazole derivatives.

Method: Ni-MOF was prepared using the modified evaporation method and was characterized by FE-SEM, FT-IR, TGA, and XRD techniques.The catalyst was then used to test the synthesis of some benzimidazole and benzothiazole derivatives. The benzimidazoles and benzothiazoles were characterized by Elemental analyses, HNMR and IR techniques.

Result: A variety of aromatic aldehydes bearing electron donating groups or electron-withdrawing were reacted with 1,2-phenylenediamine or 2-aminothiophenol using Ni-MOF in good to excellent yields.

Conclusion: In summary, a new and highly efficient method was developed and reported for the synthesis of benzimidazole and benzothiazole derivatives using nickel(II) metal-organic framework. The advantages are short reaction times, good to excellent yields, the environmentally benign and simple procedure, stability, nontoxicity, recyclability, and easy separation of the catalyst.

Keywords: Benzimidazole, benzothiazole, metal-organic framework, heterogeneous catalyst, 1, 2-phenylenediamine, 2-aminothiophenol.

Graphical Abstract

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