Silica Supported Fluoroboric Acid: An Efficient and Reusable Heterogeneous Catalyst for Facile Synthesis of 2-Aliphatic Benzothiazoles, Benzoxazoles, Benzimidazoles and Imidazo[4,5-b]pyridines

in Wiley Online Library (wileyonlinelibrary.com).Various novel benzimidazole entities linked to pyrazolyl and hydrazonoyl cyanide substrates carrying aryl and heteroaryl groups (8a-e to 10a-e) were synthesized using new route syntheses and were focused on their pharmacological evaluation as one of the most important factors for the determination of the activity of these synthesized compounds. The obtained benzimidazoles' series were fully characterized and exhibited remarkable pharmacological activity upon in vitro screening for their antibacterial activity against strains of selected pathogenic Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli) comparing with Ampicillin and Kanamycin as standard antibacterial agents and against human liver cancer cell lines (HepG2) as antitumor agents as well.

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“…The obtained product was recrystallized from acetone to give red crystals. Yield 86%, mp 140-141°C (60°C [44], 59-61°C [45]).…”

Section: General Procedures For the Synthesis Of 2-(bromomethyl)-1h-bementioning

confidence: 99%

Synthesis and Pharmacological Investigations of Novel Pyrazolyl and Hydrazonoyl Cyanide Benzimidazole Entities

Khalifa

Gobouri

Kabli

et al. 2019

Journal of Heterocyclic Chem

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“…The most common ways which are used for the synthesis of these heterocycles are treatment of o ‐phenylenediamine, o ‐aminobenzenethiol and o ‐aminophenol with nitriles, orthoesters and imidates under strongly acidic conditions. These hetrocyclic compounds can also be obtained from the reaction of the above mentioned materials with aldehydes, under the influence of various catalysts and oxidants such as iodine, oxone, FeCl 3 .6H 2 O, In(OTf) 3 , KHSO 4 , ZrOCl 2 .8H 2 O, ZrCl 4 , Heuland natural zeolite, polymer‐supported hypervalent iodine, TsOH/graphite, cobalt(III) salen complex on activated carbon, and copper iodide . Despite the interesting features of the used catalysts, introduction of a new catalyst which contains features including high activity and selectivity and easy separation and recovery all together for the synthesis of these compounds still poses a considerable challenge.…”

Section: Introductionmentioning

confidence: 99%

Periodic Mesoporous Organosilica Containing Bridged N‐Sulfonic Acid Groups: Promotion of the Synthesis of N,N’‐Diarylformamidines, Benzoxazoles, Benzothiazoles and Benzimidazoles

2019

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In this study, the successful synthesis of periodic mesoporous organosilica containing bridged N‐sulfonic acid groups (SA‐PMO) is demonstrated. The formation and morphology of the reagent were confirmed by N2 adsorption‐desorption isotherms and pH measurement, X‐ray diffraction (XRD), transmission electron microscopy (TEM) and Fourier transform infrared (FT‐IR) analysis. After identification, the catalytic activity of this reagent was investigated in the synthesis of N,N’‐diarylformamidines, benzoxazoles, benzothiazoles and benzimidazoles. Eco‐friendly protocol, excellent yields, short reaction times, ease of preparation, reusability of the catalyst and easy isolation of the products are the main advantages of this protocol. The considerable efficiency of the catalyst can be related to its high surface area, large pore volume and high acidity.

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“…Jacob et al [28] synthesized 1,2-disubstituted benzimidazoles by silica supported ZnCl 2 catalyst that was found to be of poor yield. Patil et al [29] developed a method for synthesis of 2-alkyl benzimidazoles using silica supported HBF 4 . Paul and Basu [30] described the synthesis of 1,2-disubstituted benzimidazoles by using silica gel soaked with Fe 2 (SO 4 ) 3 · x H 2 O.…”

Section: Introductionmentioning

confidence: 99%

A Simple, Efficient Synthesis of 2-Aryl Benzimidazoles Using Silica Supported Periodic Acid Catalyst and Evaluation of Anticancer Activity

Sontakke

Ghosh

Lawande

et al. 2013

ISRN Organic Chemistry

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A new, efficient method for the synthesis of 2-aryl substituted benzimidazole by using silica supported periodic acid (H5IO6-SiO2) as a catalyst has been developed. The salient feature of the present method includes mild reaction condition, short reaction time, high yield and easy workup procedure. The synthesized benzimidazoles exhibited potent anticancer activity against MCF7 and HL60 cell lines.

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Silica Supported Fluoroboric Acid: An Efficient and Reusable Heterogeneous Catalyst for Facile Synthesis of 2-Aliphatic Benzothiazoles, Benzoxazoles, Benzimidazoles and Imidazo[4,5-b]pyridines

Cited by 23 publications

References 33 publications

Synthesis and Pharmacological Investigations of Novel Pyrazolyl and Hydrazonoyl Cyanide Benzimidazole Entities

Synthesis and Pharmacological Investigations of Novel Pyrazolyl and Hydrazonoyl Cyanide Benzimidazole Entities

Periodic Mesoporous Organosilica Containing Bridged N‐Sulfonic Acid Groups: Promotion of the Synthesis of N,N’‐Diarylformamidines, Benzoxazoles, Benzothiazoles and Benzimidazoles

A Simple, Efficient Synthesis of 2-Aryl Benzimidazoles Using Silica Supported Periodic Acid Catalyst and Evaluation of Anticancer Activity

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