A Practical Synthesis of 2,4(5)-Diarylimidazoles from Simple Building Blocks

Zuliani, Valentina; Cocconcelli, Giuseppe; Fantini, Marco; Ghiron, Chiara; Rivara, Mirko

doi:10.1021/jo070187d

Cited by 60 publications

(25 citation statements)

References 15 publications

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“…The majority of the compounds were already reported and the synthesis of the novel derivatives has relied on the established synthetic protocol [33]. Briefly, the reaction is carried out from the suitable substituted phenylglyoxal and aldehyde, using ammonium acetate as an ammonia source and methanol at room temperature, with yields ranging from 30 to 51% (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

Discovery of antitubercular 2,4-diphenyl-1H-imidazoles from chemical library repositioning and rational design

Pieroni

Wan

Zuliani

et al. 2015

European Journal of Medicinal Chemistry

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Section: Chemistrymentioning

confidence: 99%

Discovery of antitubercular 2,4-diphenyl-1H-imidazoles from chemical library repositioning and rational design

Pieroni

Wan

Zuliani

et al. 2015

European Journal of Medicinal Chemistry

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“…On other hand, imidazole pharmacophore is present in several pharmacologically active organic molecules including natural products. For example, imidazole scaffold is present in the benzodiazepine antagonist flumazenil, amino acid histidine, the antiulcerative agent cimetidine, the hypnotic agent etomidate, the proton pump inhibitor omeprazole, and so on [ 7 ]. Subsequently, there is a continuous need to develop concise and rapid method for the preparation of biologically important and medicinally active imidazole derivatives.…”

Section: Resultsmentioning

confidence: 99%

An expeditious green route toward 2-aryl-4-phenyl-1H-imidazoles

Bandyopadhyay¹,

Smith²,

Garcia³

et al. 2014

Org Med Chem Lett

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BackgroundAzaheterocycles are an important class of compounds because of their highly potent medicinal activities, and the imidazole subcategory is of special interest in regard to drug discovery research.FindingsAn expeditious synthetic protocol of 2-aryl-4-phenyl-1H-imidazoles has been accomplished by reacting phenylglyoxal monohydrate, ammonium acetate, and aldehyde under sonication. Following this green approach a series of 2-aryl-4-phenyl-1H-imidazoles has been synthesized using diversely substituted aldehydes.ConclusionsA rapid and simple synthetic procedure to synthesize diversely substituted 2-aryl-4-phenyl-1H-imidazoles has been reported. Other salient features of this protocol include milder conditions, atom-economy, easy extraction, and minimum wastes. The present procedure may find application in the synthesis of biologically active molecules.Graphical AbstractAn expeditious synthetic protocol of 2-aryl-4-phenyl-1H-imidazoles has been accomplished by reacting phenylglyoxal monohydrate, ammonium acetate, and diversely substituted aldehydes under sonication.

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“…Cocconcelli et al. described a reaction of phenylglyoxal, benzaldehyde, and ammonium acetate, which proceeded well in methanol, providing 2,4(5)‐diphenylimidazole in good yield . The authors postulated that, in methanol, phenylglyoxal shifted toward the hemiacetal form.…”

Section: Aliphatic Axb3 Smentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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A Practical Synthesis of 2,4(5)-Diarylimidazoles from Simple Building Blocks

Cited by 60 publications

References 15 publications

Discovery of antitubercular 2,4-diphenyl-1H-imidazoles from chemical library repositioning and rational design

Discovery of antitubercular 2,4-diphenyl-1H-imidazoles from chemical library repositioning and rational design

An expeditious green route toward 2-aryl-4-phenyl-1H-imidazoles

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

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