Convenient Method for the Preparation of 2‐Aryl‐1H‐benzimidazole‐4‐carboxylic Acids

Cheng, Jun; Xiu, Naiyun; Li, Xiangbin; Luo, Xiaobing

doi:10.1080/00397910500188942

Cited by 10 publications

(4 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The effect of other oxidants such as p-chloranil [9], ferric chloride [26] and potassium ferricyanide [27] on the yield of corrole was also investigated in Amberlyst 15 catalyzed condensation of 1c with pyrrole (1:2 ratio) ( Table 1). Chloranil showed more selectivity but less reactivity than DDQ as 2c was obtained in higher yield and longer reaction time using chloranil as compared to DDQ ( Table 1, entries 8 and 11).…”

Section: Resultsmentioning

confidence: 99%

Efficient synthesis of 5,10,15‐triarylcorroles using amberlyst 15 under solvent‐free conditions

Kumari

Chauhan

2008

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

An efficient and convenient synthesis of 5,10,15-triarylcorroles by the condensation of aryl aldehydes with pyrrole catalyzed by Amberlyst 15 followed by oxidative cyclization with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) at room temperature has been reported. Amberlyst 15 is more efficient catalyst under solvent free conditions and DDQ is more suitable oxidant in dichloromethane than those of other catalysts and oxidants, respectively, for the synthesis of corroles at room temperature.

show abstract

Section: Resultsmentioning

confidence: 99%

Efficient synthesis of 5,10,15‐triarylcorroles using amberlyst 15 under solvent‐free conditions

Kumari

Chauhan

2008

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Some of the process are eventuate by using hydrochloric acid or phosphoric acid in refluxing at 250 o C. 12 There is a second route to synthesize benzimidazoles by condensation which is usually take place between aldehydes and ortho-phenylenediamines. 9,[23][24][25][26] Nevertheless, most of the reported routes are some limitations manly low yields, high reaction temperatures, drastic reagents used, purification difficulties and formation of by-products. Under acid medium and thermal conditions formed 1,2-disubstituted by-products (4, Scheme 1) along with the desired product (3, Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Vanadyl Acetylacetonate-Copper (II) Trifluoro Methane Sulfonate Catalyzed Eco-friendly Synthesis of Substituted Benzimidazoles in Aqueous Media

Halder¹

2020

Orient. J. Chem

View full text Add to dashboard Cite

Various substituted benzimidazoles have been successfully synthesized in aqueous medium by developing VO(acac) 2 -Cu(OTf) 2 catalytic system. A green synthetic protocol has been created in presence of water and cetyltrimethyl ammonium bromide (CTAB) system in an organic solvent free condition. This chemoselective cyclocondensation cumoxidation process occurred in aqueous media. In this suitable method easily synthesized 2-Substituted benzimidazoles with good yields and no 1,2-disubstituted by-products were noticed. Excellent yields, environmentally benign and mild reaction condition, easy purification of the desired products are the main attractive features of this newly devised method.

show abstract

“…The synthetic strategy is outlined in Scheme 1. In the initial step, suitably substituted 2,4-benzimidazole derivative was synthesized, adopting a published method with modification (44). Oxidative cyclization of 2,3-diaminobenzoic acid and 3-phenylpropionaldehyde utilizing potassium ferricyanide as an oxidant gave 2-(3-phenylethyl)benzimidazole-4-carboxylic acid (3) with moderate yield.…”

Section: -Hydroxy-3-[2-(β-phenylethyl)-1h-benzimidazole-4-yl]mentioning

confidence: 99%

Characterization of the Antiallergic Drugs 3-[2-(2-Phenylethyl) benzoimidazole-4-yl]-3-hydroxypropanoic Acid and Ethyl 3-Hydroxy-3-[2-(2-phenylethyl)benzoimidazol-4-yl]propanoate as Full Aryl Hydrocarbon Receptor Agonists

Morales

Krzeminski

Amin

et al. 2008

Chem. Res. Toxicol.

View full text Add to dashboard Cite

The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates most of the toxic effects of numerous chlorinated (e.g., TCDD) and nonchlorinated polycyclic aromatic compounds (e.g., benzo[a]pyrene). Studies in AhR null mice suggested that this receptor may also play a role in the modulation of immune responses. Recently, two drugs, namely, M50354 and M50367 (ethyl ester derivative of M50354), were described as AhR ligands with high efficacy toward reducing atopic allergic symptoms in an AhR-dependent manner by skewing T helper cell differentiation toward a T H 1 phenotype [Negishi et al. (2005) J. Immunol. 175 (11), 7348-7356]. Surprisingly, these drugs were shown to have minimal activity toward inducing classical dioxin responsive element-driven AhR-mediated CYP1A1 transcription. We synthesized and reevaluated the ability of these drugs to regulate AhR activity. In contrast to previously published data, both M50354 and M50367 were found to be potent inducers of several AhR target genes, namely, CYP1A1, CYP1B1, and UGT1A2. M50367 was a more effective agonist than M50354, perhaps accounting for its higher bioavailability in vivo. However, M50354 was capable of displacing an AhR-specific radioligand more effectively than M50367. This is consistent with M50354 being the active metabolite of M50367. In conclusion, two selective inhibitors of T H 2 differentiation are full AhR agonists.

show abstract

Convenient Method for the Preparation of 2‐Aryl‐1H‐benzimidazole‐4‐carboxylic Acids

Cited by 10 publications

References 7 publications

Efficient synthesis of 5,10,15‐triarylcorroles using amberlyst 15 under solvent‐free conditions

Efficient synthesis of 5,10,15‐triarylcorroles using amberlyst 15 under solvent‐free conditions

Vanadyl Acetylacetonate-Copper (II) Trifluoro Methane Sulfonate Catalyzed Eco-friendly Synthesis of Substituted Benzimidazoles in Aqueous Media

Characterization of the Antiallergic Drugs 3-[2-(2-Phenylethyl) benzoimidazole-4-yl]-3-hydroxypropanoic Acid and Ethyl 3-Hydroxy-3-[2-(2-phenylethyl)benzoimidazol-4-yl]propanoate as Full Aryl Hydrocarbon Receptor Agonists

Contact Info

Product

Resources

About