Cobalt manganese oxide nanoparticles as recyclable catalyst for efficient synthesis of 2‐aryl‐1‐arylmethyl‐1H‐1,3‐benzimidazoles under solvent‐free conditions

Ahmadian, Hossein; Veisi, Hojat; Karami, Changiz; Sedrpoushan, Alireza; Nouri, Maryam; Jamshidi, Fariba; Alavioon, Iman

doi:10.1002/aoc.3283

Cited by 17 publications

(11 citation statements)

References 30 publications

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“…The satisfactory results from these scale-up experiments further confirmed the advantage of this simple and "green" protocol for its potential in large-scale synthesis. a) General conditions: o-phenylenediamine (1 mmol) and Ia (2 mmol) in lactic acid (2 mL), stirred at ambient temperature for 4-6 h; b) yield of isolated product; c) values reported in literature Chebolu et al, 2012;Ahmadian et al, 2015); d) reaction at 80 • C and purified by silica gel column chromatography. From the experimental observations and literature reports on experiments carried out under similar reaction conditions , a plausible reaction mechanism for the selective formation of 1,2-substituted benzimidazoles in lactic acid was proposed (Fig.…”

Section: Resultsmentioning

confidence: 99%

Chemoselective synthesis of 1,2-disubstituted benzimidazoles in lactic acid without additive

Zhou

Fang

et al. 2016

Chemical Papers

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Lactic acid is recognised as a biocompatible medium for the chemoselective synthesis of the 1,2-disubstituted benzimidazole scaffold via a direct one-pot cyclocondensation of o-phenylenediamine with aldehydes. Various 1,2-disubstituted benzimidazole derivatives were successfully synthesised with high selectivity with good to excellent yields without any additional catalyst or additive. Most products could be isolated by a simple filtration after completion of the reactions. Satisfactory results were also obtained from multi-gram scale reactions.

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Section: Resultsmentioning

confidence: 99%

Chemoselective synthesis of 1,2-disubstituted benzimidazoles in lactic acid without additive

Zhou

Fang

et al. 2016

Chemical Papers

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“…Ahmadian et al ., using the same protocol, proposed a green solvent‐free synthesis of 2‐aryl‐1‐arylmethyl‐1 H ‐1,3‐benzimidazoles ( 27 ) by employing cobalt manganese oxide nanoparticles as catalyst. The condensation of o ‐phenylenediamine ( 4 ) and aryl aldehyde ( 26) yielded 85–97% of the product at 80°C in 5–20 min (Scheme ) .…”

Section: Nano‐transition Metal Catalyzed Oxidative Coupling Of O‐phenmentioning

confidence: 99%

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

Singhal

Khanna

Panda

et al. 2019

Journal of Heterocyclic Chem

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Benzimidazole is a heterocyclic moiety of immense importance as it acts as a primary “biolinker” in diverse synthetic routes to obtain bioactive compounds. Substituted benzimidazoles are known to possess a varied range of pharmacological applications, namely, anti‐cancer, anti‐diabetic, anti‐inflammatory, and antiviral like anti‐HIV and anti‐fungal. A number of reviews covering the important aspects of benzimidazoles such as pharmacological activities, SAR studies, and well‐known methods of synthesis have appeared in the literature. However, green synthetic methods particularly using transition metal (TM) catalysts and their nanoparticles, although being more viable and extensively applied by researchers in the present scenario, have not been exclusively and expansively reviewed. Besides this, the vital precursors required for knitting the skeleton of benzimidazole are mainly o‐aryldiamines. The conventional synthesis generally involved the condensation of these diamines with carbonyl/carboxylic acid derivatives either via high temperature heating or via adding strong acids, mostly resulting in poor yields or mixtures. However, recent trends are replacing these conditions by mild and green conditions through TM catalysts. Therefore, the current review emphasizes on the recent trends adopted in the synthesis of benzimidazoles using condensation reaction of o‐phenylenediamines and various aldehydes/ester/amide/alcohols with TM in a catalytic role in nanoform and under environmentally benign green conditions.

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“…Conventionally, the synthesis of benzimidazoles involves the condensation of ophenylenediamine with aldehydes, or carboxylic acid or their derivatives in the presence of catalysts. [23][24][25][26] In the present work, we are reporting our investigations on Cr 3+ doped Ni-Cu-Zn spinel ferrite as magnetically recoverable and reusable catalyst for the synthesis of benzimidazoles. An efficient synthesis of benzimidazoles carried via one-pot two-component condensation reaction of o-phenylenediamine, aromatic aldehydes in high yields and short reaction times by using Cr 3+ doped Ni-Cu-Zn spinel ferrites with as a green, robust and easily recoverable catalyst (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

An Efficient One-Pot Synthesis of Benzimidazoles Using Magnetically Recoverable Catalyst Chromium Doped Nickel Copper Zinc Spinel Ferrite

Shinde¹,

Dhale²,

Mandle³

et al. 2019

Int. Res. J. Pharm.

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An efficient synthesis of benzimidazoles has been developed via one-pot two-component condensation reaction of o-phenylene diamine and aromatic aldehydes by using magnetic Cr 3+ doped Ni-Cu-Zn spinel ferrite as catalyst in ethanol. The products obtained with high yields in shorter reaction time. The Cr 3+ doped Ni-Cu-Zn spinel ferrites synthesized by sol gel auto combustion method and characterized by XRD, IR, TEM and VSM. The XRD patterns confirmed single phase of cubic spinel structure of catalyst. Lattice constant of catalyst decreased from 8.418 Å to 8.406 Å, while percentage porosity increases from 25.4 % to 27.7 % with increase in Cr 3+ content. The crystallite size decreased from 30.3 nm to 19.1 nm with increase in Cr 3+ content. Cr 3+ doped Ni-Cu-Zn spinel ferrites were soft magnetic materials. The catalyst can be robust and easily recoverable using external magnetic field and reused five times with almost the same catalytic activity. The proposed method is advantageous due to its small catalyst loading, short reaction time, magnetically catalyst recovery, catalyst reusability and better yields.

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Cobalt manganese oxide nanoparticles as recyclable catalyst for efficient synthesis of 2‐aryl‐1‐arylmethyl‐1H‐1,3‐benzimidazoles under solvent‐free conditions

Cited by 17 publications

References 30 publications

Chemoselective synthesis of 1,2-disubstituted benzimidazoles in lactic acid without additive

Chemoselective synthesis of 1,2-disubstituted benzimidazoles in lactic acid without additive

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

An Efficient One-Pot Synthesis of Benzimidazoles Using Magnetically Recoverable Catalyst Chromium Doped Nickel Copper Zinc Spinel Ferrite

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