Glyoxylic acid as catalyst: A simple selective synthesis of 1,2-disubstituted benzimidazoles in aqueous media

Pawar, Shivaji S.; Dekhane, Deepak V.; Shingare, Murlidhar S.; Thore, Shivaji N.

doi:10.1016/j.cclet.2008.06.028

Cited by 30 publications

(9 citation statements)

References 36 publications

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“…The traditional synthesis of benzimidazoles involves the reaction between an o ‐phenylenediamine and a carboxylic acid or its derivatives (nitriles, amidates, orthoesters) under harsh dehydrating conditions . Very recently, a literature survey revealed several methods for synthesis of benzimidazole and its derivatives using l ‐proline, glyoxalic acid, SiO 2 /ZnCl 2 , Fe(ClO 4 ) 3 , trimethylsilyl chloride, silica sulfuric acid, oxalic acid, mesoporous metal oxide nanocrystals, Indion 190 resin, sodium dodecylsulfate–water, nano‐In 2 O 3 and alumina–sulfuric acid …”

Section: Introductionmentioning

confidence: 99%

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

Ahmadian

Veisi

Karami

et al. 2015

Applied Organom Chemis

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Section: Introductionmentioning

confidence: 99%

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

Ahmadian

Veisi

Karami

et al. 2015

Applied Organom Chemis

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“…Synthesis of benzimidazoles in aqueous media using Znproline 17 , silica sulfuric acid 18 and glyoxylic acid 19 as catalyst and high temperature in water 20 have been reported in the documents.…”

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confidence: 99%

Synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles Catalyzed by Brønsted Acidic Ionic Liquid under Ultrasonic Irradiation

Liu¹,

Gao²,

Zhang³

et al. 2014

Asian J. Chem.

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Benzimidazole and their derivatives have diverse applications in medicinal chemistry because of their unique biological and pharmacological activities. Many members of this family have commercial applications in various realms of therapy, including antiulcerative, antihypertensive, antiviral, antifungal, antitumor and antihistaminic agents and antihelminthic agents in veterinary medicine [1][2][3][4][5][6][7] . Due to their affinity towards enzymes and protein receptors, they have been appropriately classified as 'privileged sub-structures' for drug design. Moreover, benzimidazoles are very important intermediates in various organic reactions 8 . Therefore, the preparation of benzimidazoles has received considerable attention in recent years.Until now, many synthetic strategies for the preparation of benzimidazoles have been reported in the literature. Generally, they are synthesized through the condensation reaction of o-phenylenediamines and carboxylic acids or their derivatives (nitriles, amidates, orthoesters) 9 in the presence of strong acids such as polyphosphoric acid 10 or mineral acids 11 . Benzimidazoles have also been prepared by the condensation reaction of aldehyde and arylenediamine under oxidative conditions [12][13][14][15] . However, each of these methodologies suffer from one or more shortcomings, such as low yields, long reaction times, using toxic catalyst and solvents, tedious workup procedures and co-occurrence of several side reactions.Organic reactions in aqueous media have attracted great interest due to its safety, low cost and environmental friendly 16 .

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“…Benzimidazole and its derivatives have been used as the antiulcerative esomeprazole [7,8] and in diverse human therapeutic areas as an antiulcer and antihistaminic [9]. The condensation of an arylene diamine with a carboxylic acid or its derivative under harsh dehydrating reaction conditions is the most popular synthesis of these materials [10,11]. Another method for synthesis of this compound is the condensation of arylene diamine with an aldehyde [11,12].…”

Section: Introductionmentioning

confidence: 99%

“…The condensation of an arylene diamine with a carboxylic acid or its derivative under harsh dehydrating reaction conditions is the most popular synthesis of these materials [10,11]. Another method for synthesis of this compound is the condensation of arylene diamine with an aldehyde [11,12]. Herein, in this work we have reported PBNS as a novel, heterogeneous, and reusable catalyst for the condensation of O-phenylenediamine (OPD) with aryl aldehydes to give corresponding 2-arylbenzimidazoles and 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Application of Poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide) as an Efficient Reagent for the Synthesis of 2-Arylbenzimidazole and 2-Aryl-1-arylmethyl-1H-1,3-benzimidazole Derivatives

Saleh

Khazaei

Abizadeh

et al. 2015

Organic Chemistry International

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The condensation of O-phenylenediamine (OPD) with aryl aldehydes is carried out in acetonitrile using poly(N,N -dibromo-N-ethylnaphthyl-2,7-disulfonamide) (PBNS) as a novel and heterogeneous catalyst. PBNS has some potential advantages which include ease of separation from the reaction mixture by simple filtration, easy preparation, recoverablility, convenience, and stability under normal condition and also is not dangerous as molecular bromine.

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Glyoxylic acid as catalyst: A simple selective synthesis of 1,2-disubstituted benzimidazoles in aqueous media

Cited by 30 publications

References 36 publications

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

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

Synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles Catalyzed by Brønsted Acidic Ionic Liquid under Ultrasonic Irradiation

Synthesis, Characterization, and Application of Poly(N,N′-dibromo-N-ethylnaphthyl-2,7-disulfonamide) as an Efficient Reagent for the Synthesis of 2-Arylbenzimidazole and 2-Aryl-1-arylmethyl-1H-1,3-benzimidazole Derivatives

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