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A Review on Modern Approaches to Benzimidazole Synthesis

Affiliation.

• 1 Department of Pharmaceutical Sciences, School of Pharmacy, Lovely Professional University, Punjab, 144001, India.
• PMID: 36221870
• DOI: 10.2174/1570179420666221010091157

Cancer is the second most source of cessation of life globally, with 9.6 million expirations at each stage around the globe. The resistance to the current chemotherapies urges researchers to develop new drugs to be available in the market. Among the wide range of drugs synthesized, heterocyclic compounds play a major role due to the abundance of heterocyclic rings in biological substances. In medicinal chemistry, benzimidazole is an important pharmacophore and a privileged structure. This bicyclic compound is made up of the fusion of a six-membered benzene ring and a five-membered imidazole ring with two nitrogen atoms at 1,3-positions. The benzimidazole ring has a great deal of stability. Many strong acids and alkalis do not affect benzimidazoles. The benzene ring of benzimidazole cleaves only under extreme conditions. Except in certain circumstances, the benzimidazole ring is also quite resistant to reduction. It is the most popular nucleus to study because of its wide range of biological functions. The recently developed methods for preparing benzimidazoles, such as condensation of o-phenylene diamines (OPDs) with aldehydes and many others using a wide range of nano, metal-based catalysts under solventfree conditions, are discussed in detail in the current studies.

Keywords: Benzimidazoles; cancer; malignant neoplasm; nanocatalysts; o-phenylene diamine; solvent-free techniques pharmacophore.

Copyright© Bentham Science Publishers; For any queries, please email at [email protected].

The Nano-Based Catalyst for the Synthesis of Benzimidazoles

• Original Paper
• Published: 10 February 2022

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• Rangappa S. Keri 1 ,
• Vinayak Adimule 2 ,
• Pravin Kendrekar 3 &
• B. S. Sasidhar 4 , 5  

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The properties of benzimidazole and its derivatives have been studied over more than one hundred years. The benzimidazole ring is an important pharmacophore in modern drug discovery. Benzimidazole-based compounds possess potential application as medicinal drugs, presently; more than 20 drugs are available for the treatment of different diseases. Also, this motif is considered as privileged structure in medicinal chemistry because of its wide range of biological activities viz., antibacterial, antifungal, anticonvulsant, anti-tubercular, anti-HIV, anti-diabetic, anti-oxidant, anticancer, anti-inflammatory, analgesic antileishmanial, and antihistaminic agents etc. Owing to the diverse therapeutic applications, the incorporation of benzimidazole nucleus has become a field of high interest to organic and medicinal chemists. The various key starting materials (KSMs) utilized includes, aromatic and heteroaromatic 2-nitro-amines, phenylenediamine, carboxylic acids or its derivatives. However, these classical methods suffer from demerits such as, low atom economy, the formation of by-products, harsh reaction conditions, extended reaction period, expensive catalysts, and unsatisfactory yield of products as well as toxic solvents. Hence, the chemists have their attention towards developing synthetic processes primarily based on the set of principles of green chemistry. In this context, many efficient methods were developed for the synthesis of benzimidazole using the nanocatalyst or nanostructures. In this review, special emphasis has been given to discuss the “green” synthetic techniques adopted for the preparation of functionalized benzimidazole congeners as well as key mechanistic considerations and future outlook in this area. In this review, the literature up to the November 2021 in which very recently reported synthetic routes to access benzimidazole scaffolds are discussed. We are focused on, in particular, the synthetic methodologies/routes to construct 2-substituted/1,2-disubstituted benzimidazole or benzimidalones via various protocols involving condensation, cyclization, metal-free conditions, solvent-free conditions, and using nanocatalyst. This review will further aid the researcher to in developing more efficient and facile methods for the synthesis of benzimidazoles and associated hybrids.

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In this review, special emphasis has been given to discuss the “green” synthetic techniques adopted for the preparation of functionalized benzimidazole congeners as well as key mechanistic considerations and future outlook in this area. In this review, the literature up to the November 2021, in which very recently reported synthetic routes to access benzimidazole scaffolds are discussed. In particular, the synthetic methodologies/routes to construct 2-substituted/1,2-disubstituted benzimidazole or benzimidalones via various protocols involving condensation, cyclization, metal-free, solvent-free, and using nanocatalyst. This review will further aid the researcher in developing more efficient and facile methods for the synthesis of benzimidazoles and associated hybrids.

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Abbreviations.

Brunauer–Emmett–Teller

Bismuth oxychloride

Energy dispersive X-ray analysis

Electron donating groups

Electron withdrawing group

Field emission scanning electron microscopy

Fourier transformer infrared spectroscopy

Inductively coupled plasma

Indium oxide

o -Phenylenediamine

Nitrogen adsorption–desorption isotherms

Transmission electron microscopy

Thermogravimetry analysis

Powder X-ray diffraction

X-ray photoelectron spectrometer

Value stream mapping

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Thanks to the Jain University, for financial support.

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Organic and Medicinal Chemistry Laboratory, Centre for Nano and Material Sciences, Jain University, Jain Global Campus, Jakkasandra Post, Kanakapura Road, Ramanagara District, Bangalore, Karnataka, 562112, India

Rangappa S. Keri

Angadi Institute of Technology and Management (AITM), Savagaon Road, Belagavi, Karnataka, 5800321, India

Vinayak Adimule

Lipid Nanostructures Laboratory, Centre for Smart Materials, School of Natural Sciences, University of Central Lancashire, Preston, UK

Pravin Kendrekar

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

B. S. Sasidhar

Organic Chemistry Section, Chemical Sciences and Technology Division, Council of Scientific and Industrial Research (CSIR)–National Institute for Interdisciplinary Science and Technology (NIIST), Thiruvananthapuram, 695019, India

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Keri, R.S., Adimule, V., Kendrekar, P. et al. The Nano-Based Catalyst for the Synthesis of Benzimidazoles. Top Catal (2022). https://doi.org/10.1007/s11244-022-01562-0

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DOI : https://doi.org/10.1007/s11244-022-01562-0

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Current Organic Synthesis

Editor-in-Chief: Qingmin Wang State Key Laboratory of Elemento-Organic Chemistry Nankai University Tianjin P.R. China

ISSN (Print): 1570-1794 ISSN (Online): 1875-6271

One Pot Synthesis of New Benzimidazole Derivatives with Exceptionally High Luminescence Quantum Efficiency

• School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, 212003, P. R. China

Volume 21, Issue 8, 2024

Published on: 11 January, 2024

Page: [1091 - 1101] Pages: 11

DOI: 10.2174/0115701794271985231219070212

Conclusion: Five new benzimidazole derivatives, BMPO, Me-BMPO, Di-MeBIPO, F-BIPO, and Cl-BIPO, have been successfully synthesized by the one-pot synthesis method, and their structures are characterized and confirmed. The compounds exhibited exceptional luminescence by emitting a strong blue light in DMA with high fluorescence quantum yields between 42~80%.

Keywords: Heterocycle compounds , benzimidazole , luminescence , quantum yield , one-pot synthesis.

Title: One Pot Synthesis of New Benzimidazole Derivatives with Exceptionally High Luminescence Quantum Efficiency

Volume: 21 Issue: 8

Author(s): Abraham Mensah, Xin-Ye Liu, Bing-Xiang Hu, Ennin Vendish Kweku, Fang-Ming Wang*, Li-Zhuang Chen*Shao-Jun Zheng*

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Mensah Abraham, Liu Xin-Ye, Hu Bing-Xiang, Kweku Vendish Ennin, Wang Fang-Ming*, Chen Li-Zhuang*, Zheng Shao-Jun*, One Pot Synthesis of New Benzimidazole Derivatives with Exceptionally High Luminescence Quantum Efficiency, Current Organic Synthesis 2024; 21 (8) . https://dx.doi.org/10.2174/0115701794271985231219070212

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