1740-25-6

Usage

Class of compound

Imidazole

Structure

Five-membered aromatic ring with two nitrogen atoms and three carbon atoms

Substituents

2-(2-bromophenyl) and 4,5-diphenyl

Reactivity

Versatile

Therapeutic properties

Potential antifungal and antibacterial properties

Applications

Organic synthesis, pharmaceutical research, and drug development.

Upstream product

• 134-81-6 benzil 
• 6630-33-7 ortho-bromobenzaldehyde 
• 119-53-9 2-hydroxy-2-phenylacetophenone 

Downstream Products

• 52747-80-5 2,3-diphenylimidazo[1,2-c]quinazoline 

Relevant academic research and scientific papers

Copper-Catalyzed Synthesis of Dibenzo[ b, f ]imidazo[1,2- d ][1,4]oxazepine Derivatives via a Double Ullmann Coupling Reaction

A double Ullmann coupling reaction successfully takes place between 4,5-diaryl-2-(2-bromophenyl)-1 H -imidazoles and 2-bromophenols in the presence of Cs 2 CO 3. This procedure is catalyzed by copper(I) iodide and o -phenanthroline a

Isocyanide Insertion-Cyclization Reaction for Imidazoisoindol-5-imine Scaffold Synthesis: A Selective Solvatochromic Fluorescent Probe for Methanol Detection

An efficient, ligand-free, and Pd-catalyzed method for the synthesis of imidazoisoindole imine scaffolds with satisfactory yields via C-C and C-N bond formation has been developed. The synthesized scaffolds have unique potential for selective MeOH detecti

Construction of trinuclear N-fused hybrid scaffolds by coupling and cyclization of 2-bromoaryl- and 2-bromovinylimidazoles with ureas under recyclable Cu/C–Al2O3 catalysis

2-(2-Bromoaryl)- and 2-(2-bromovinyl)imidazoles are coupled and cyclized with cyclic ureas as building blocks under recyclable heterogeneous Cu/C–Al2O3 catalysis to afford a class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]imidazo[1,2-c]quinazolines and benzo[4,5]imidazo[1,2-a]imidazo[1,2-c]pyrimidines, respectively. The Cu/C–Al2O3 catalytic system could be recovered and reused three times without any loss of catalytic activity.

TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions

In the process of drug discovery and development, an efficient and expedient synthetic method for imidazole-based small molecules from commercially available and cheap starting materials has great significance. Herein, we developed a TMSOTf-catalyzed synthesis of trisubstituted imidazoles through the reaction of 1,2-diketones and aldehydes using hexamethyldisilazane as a nitrogen source under microwave heating and solvent-free conditions. The chemical structures of representative trisubstituted imidazoles were confirmed using X-ray single-crystal diffraction analysis. This synthetic method has several advantages including the involvement of mild Lewis acid, being metal- and additive-free, wide substrate scope with good to excellent yields and short reaction time. Furthermore, we demonstrate the application of the methodology in the synthesis of biologically active imidazole-based drugs.

Facile synthesis of imidazoles by an efficient and eco-friendly heterogeneous catalytic system constructed of Fe3O4 and Cu2O nanoparticles, and guarana as a natural basis

In this study, an efficient hybrid nanocatalyst made of guar gum (guarana, as a natural basis), magnetic iron oxide nanoparticles, and copper(I) oxide nanoparticles (Cu2O NPs) is fabricated and suitably applied for catalyzing the multicomponent (three- and four-component) synthesis reactions of imidazole derivatives. Here, an easy preparation strategy for this novel catalytic system (Cu2O/Fe3O4@guarana) is presented. Then, the application of this catalytic system for the synthesis of imidazole derivatives is precisely investigated. For this purpose, ultrasonication is introduced as an efficient and fast method. In summary, the high catalytic efficiency of Cu2O/Fe3O4@guarana nanocomposite is well demonstrated by high reaction yields obtained in the presence of a small amount of this nanocomposite, under mild conditions. Wide active surface area, substantial magnetic behavior, excellent heterogeneity, suitable stability, well reusability, and etc. have distinguished this catalytic system as an instrumental tool for facilitating the complex synthetic reactions.

Facile fabrication of porous magnetic covalent organic frameworks as robust platform for multicomponent reaction

The design of cheap yet efficient nanoporous magnetic catalysts for the environmentally benign process's widespread application is an extremely attractive, challenging chemical research field. A novel porous magnetic covalent organic framework was prepared by the condensation reaction of melamine and terephthaladehyde on the surface of 3,4-dihydroxybenzaldehyde coated magnetic Fe3O4 nanoparticles COF@Fe3O4 under hydrothermal conditions for the first time. The high surface area magnetic COF could exhibit superior catalytic activity for sustainable synthesis of trisubstituted and tetrasubstituted imidazoles and pyrroles in good to excellent yields in PEG as solvent under environmentally friendly, ambient conditions and making the overall process economical, efficient, and green. The retrievable catalyst in PEG is general and applicable to a broad substrate scope and functional group compatibility. The structure and morphology of the COF@Fe3O4 were characterized by FTIR, XRD, EDX, and SEM spectroscopy. The COF@Fe3O4 magnetic catalyst was recovered by an external magnet and used for several cycles without significant catalytic activity loss.

Synthesis of Trinuclear Benzimidazole-Fused Hybrid Scaffolds by Transition Metal-Free Tandem C(sp2)?N Bond Formation under Microwave Irradiation

2-(2-Bromoaryl)- and 2-(2-bromovinyl)benzimidazoles have been coupled and cyclized with 2-methoxy- and 2-aryloxybenzimidazoles as building blocks in the presence of a base under microwave irradiation to give a class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo[1,2-c]quinazolines and -pyrimidines, respectively, in good yields. 2-(2-Bromoaryl)- and 2-(2-bromovinyl)imidazoles also reacted with 2-methoxybenzimidazoles in the presence of base under microwave irradiation to give a class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]imidazo[1,2-c]quinazolines and -pyrimidines, respectively, in similar yields. This process seems to proceed via an initial C(sp2)-N coupling by an addition-elimination nucleophilic aromatic substitution (SNAr) and subsequent cyclization accompanied by extrusion of alcohols.

A new nanocomposite catalyst based on clay-supported heteropolyacid for the green synthesis of 2,4,5-trisubstituted imidazoles

Intercalation of cetyltrimethylammonium (CTA+) cations within the nanolayers of montmorillonite (MMT) clay followed by reaction with Keggin-type phosphomolybdic acid (PMo) resulted in the synthesis of (CTA)3PMo-MMT nanocomposite catalyst. The prepared nanocomposite catalyst was characterized using different physicochemical methods such as Fourier-transform infrared and inductively coupled plasma–optical emission spectroscopies, X-ray diffraction, and nitrogen adsorption–desorption (Brunauer–Emmett–Teller method) analyses. Characterization techniques demonstrated the intercalation of (CTA)3PMo species into the nanolayers of MMT. The resulting (CTA)3PMo-MMT nanocomposite catalyst efficiently catalyzed the synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions. The efficiency is due to the fact that the presence of CTA+ species makes the nanocomposite catalyst hydrophobic and facilitates the accessibility of hydrophobic reactants to active sites in the course of the reaction. High activity and selectivity were achieved in the presence of the prepared nanocomposite catalyst. The nanocomposite catalyst was readily isolated from the reaction mixture using simple filtration, washed with ethanol, and recycled five times without a major loss of activity.

A 2, 4, 5 - tri-substituted imidazole of preparation method (by machine translation)

The invention relates to a 2, 4, 5 - tri-substituted imidazole of preparation method, the method is to be sequentially [...] or benzoins, aldehyde compounds, ammonium acetate and catalyst organic acid added in the reactor, in the 85 - 125 °C oil bath under the heating condition the reaction, after the reaction is complete to obtain a reaction mixture; the reaction mixture by washing, filtration, recrystallization after separation, to get the pure product 2, 4, 5 - tri-substituted imidazole. The present invention is simple, the production cost is low, and the yield is high, and has a good industrial application prospect. (by machine translation)

Design and preparation of ZnS-ZnFe2O4: a green and efficient hybrid nanocatalyst for the multicomponent synthesis of 2,4,5-triaryl-1H-imidazoles

In the present work, a new protocol was introduced for the preparation of an efficient hybrid nanocatalyst ZnS-ZnFe2O4 via the co-precipitation method as well as its application in the synthesis of 2,4,5-triaryl-1H-imidazoles derivatives starting from various aromatic aldehydes, benzil and ammonium acetate under ultrasonic irradiation in ethanol. ZnS-ZnFe2O4 was characterized by Fourier transform infrared (FT-IR) spectroscopy, energy-dispersive X-ray spectroscopy (EDS) analysis, scanning electron microscopy (SEM) image, X-ray diffraction (XRD) pattern and vibrating sample magnetometer (VSM) curve. This method has advantages such as high efficiency of the heterogeneous catalyst, the use of environmentally-friendly solvent, high yields, short reaction times and easy isolation of the products and chromatography-free purification. Our outcomes illustrated that the present nanocatalyst with nearly spherical and Cauliflower-like morphology and average particle size of 36?nm could be applied as an effective and magnetically recyclable catalyst without any significant decreasing of activity. Furthermore, the synergic effect of bimetallic Lewis acids was studied for the synthesis of imidazole derivatives.