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Upstream product

• 100-52-7 benzaldehyde 
• 119-52-8 4,4'-dimethoxybenzoin 
• 123-11-5 4-methoxy-benzaldehyde 
• 1448032-53-8 1-benzyl-4,5-di(4-methoxyphenyl)-2-phenyl-1H-imidazole 
• 126177-56-8 1-benzyl-4,5-dibromo-2-phenyl-1H-imidazole 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 

Downstream Products

• 142217-42-3 1-(7-Ethoxy-carbonylheptyl)-4,5-bis-(4-methoxyphenyl)-2-phenylimidazole 

Relevant academic research and scientific papers

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 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.

One-Pot Three-Component Synthesis of 2,4,5-Triaryl-1 H -imidazoles in the Presence of a Molecular Sieve Supported Titanium Catalyst under Mild Basic Conditions

A series of 2,4,5-trisubstituted-imidazoles has been synthesized with good to excellent yields by the one-pot condensation reaction of 1,2-dicarbonyl compounds, benzaldehydes, and ammonium acetate in the presence of 4 ? molecular sieves modified with titanium(IV) as an efficient heterogeneous catalyst. The catalyst could be recovered easily and reused without significant loss of activity.

Magnetically separable and recyclable g-C3N4 nanocomposite catalyzed one-pot synthesis of substituted imidazoles

A green, reliable synthetic method and highly efficient one-pot three-component synthesis of 2,4,5-trisubstituted imidazoles from 1,2-diketones, aldehydes and ammonium acetate in the presence of recyclable magnetic graphitic carbon nitride nanocomposite (Fe3O4@g-C3N4) has been developed. Various imidazole derivatives were obtained in moderate to excellent yields and high purity after recrystallization from ethanol. Interestingly, the low-cost Fe3O4@g-C3N4 a nontoxic and inexpensive catalyst showed excellent recyclability using an external magnet without loss of parent catalytic activity even after ten cycles and its provides new opportunities for the truly environmental friendliness methodology.

Fe3O4@chitosan nanoparticles: A valuable heterogeneous nanocatalyst for the synthesis of 2,4,5-trisubstituted imidazoles

Chitosan-coated Fe3O4 nanoparticles (Fe 3O4@CS) were prepared simply through in situ co-precipitation of Fe2+ and Fe3+ ions via NH 4OH in an aqueous solution of chitosan and their catalytic activity was investigated in the synthesis of 2,4,5-trisubstituted imidazoles by a one-pot condensation of benzil derivatives, aryl aldehydes and ammonium acetate in EtOH. This novel method offers several advantages compared to those reported in the previous literature, including avoiding the use of harmful catalysts, easy and quick isolation of the products, excellent yields, mild and clean conditions, and simplicity of the methodology. High catalytic activity and ease of recovery using an external magnetic field are additional eco-friendly attributes of this catalytic system. This journal is the Partner Organisations 2014.

Synthesis and anticancer activity of 2,4,5-triaryl imidazole derivatives

This study describes the synthesis of four 2,4,5-triarylimidazole derivatives and their anticancer activities. The target compounds were prepared from the reaction of benzaldehyde and benzoin derivatives in presence of ammonium acetate and ammonium vanadate. All the synthesized compounds were screened for anticancer activities against T47D and MDA-MB231 cell lines using the MTT assay. However, our obtained results indicated a significant difference between colchicines cytotoxicity and their homologs on treated MDA-MB231 and T47D cells; one compound (4a) showed a significant IC50 on MDA-MB231 cells in cell culture assay.

A highly efficient magnetic solid acid catalyst for synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation

Fe3O4 nanoparticles were prepared by chemical coprecipitation method and subsequently coated with 3-aminopropyltriethoxysilane (APTES) via silanization reaction. Grafting of chlorosulfuric acid on the amino-functionalized Fe3O4 nanoparticles afforded sulfamic acid-functionalized magnetic nanoparticles (SA-MNPs). SA-MNPs was found to be a mild and effective solid acid catalyst for the efficient, one-pot, three-component synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation. This protocol afforded corresponding imidazoles in shorter reaction durations, and in high yields. This green procedure has many obvious advantages compared to those reported in the previous literatures, including avoiding the use of harmful catalysts, easy and quick isolation of the products, excellent yields, short routine, and simplicity of the methodology.

Selective sequential cross-coupling reactions on imidazole towards neurodazine and analogues

Polysubstituted imidazoles represent a common structural motif in bioactive molecules. A modular and flexible strategy towards 2,4,5-triarylated imidazoles is reported applying a Suzuki-Miyaura cross-coupling protocol. Employing 1-protected 2,4,5-tribromoimidazole as starting material, both stepwise and one-pot protocols towards the title compounds are disclosed. The utility of the approach was demonstrated by synthesizing neurodazine, a biologically active molecule affecting neuronal cell differentiation.

Catalytic procedures for multicomponent synthesis of imidazoles: Selectivity control during the competitive formation of tri- and tetrasubstituted imidazoles

The catalytic potential of different fluoroboric acid-derived catalyst systems viz. aq HBF4, solid supported HBF4, metal tetrafluoroborates (inorganic salts), solid supported metal tetrafluoroborates, and tetrafluoroborate based ionic liquids (organic salts) were investigated for the three component reaction (3-MCR) of 1,2-diketone, aldehyde, and ammonium salts to form 2,4,5-trisubstituted imidazoles and the four component reaction (4-MCR) involving 1,2-diketone, aldehyde, amine and ammonium acetate to form 1,2,4,5-tetrasubstituted imidazoles. The HBF4-SiO2 was found to be the stand out catalyst for both the 3-MCR and 4-MCR processes. The next most effective catalysts are LiBF4 and Zn(BF4) 2 to form 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles via the 3-MCR and 4-MCR, respectively. This is the first report on the unaddressed issue of competitive formation of 2,4,5-trisubstituted imidazole during the 4-MCR involving 1,2-diketone, aldehyde, amine and ammonium acetate and highlights the influence of the catalyst systems in controlling the selective formation of tetra substituted imidazole. The metal salt of weak protic acids drive selectivity towards tetra substituted imidazole in the order tetrafluoroborates > perchlorates > triflates. The catalytic potency of tetrafluoroborates was in the order Zn(BF4)2 > Co(BF4)2 > AgBF4 ≈ Fe(BF 4)2 > NaBF4 ≈ LiBF4 ≈ Cu(BF4)2. The developed protocols worked well for different diketones, various aryl, heteroaryl, and alkyl aldehydes and in the case of the preparation of 1,2,4,5-tetrasubstituted imidazoles different amines can be used. The effectiveness of different ammonium salts as nitrogen source has been investigated and ammonium acetate is proved to be the best. The HBF4-SiO2 is recyclable for five consecutive uses without significant loss of catalytic activity. The Royal Society of Chemistry 2012.

Zinc (II) [tetra(4-methylphenyl)] porphyrin: A novel and reusable catalyst for efficient synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation

An efficient three-component one-step synthesis of 2,4,5-trisubstituted imidazoles by condensation reaction of 1,2-diketones or a-hydroxyketones with aromatic aldehydes and ammonium acetate using Zinc (II) [tetra (4-methylphenyl)] porphyrin as a novel and reusable catalyst under ultrasound irradiation at ambient temperature is described. In this method, a-hydroxyketones as well as 1,2-diketones were converted to their corresponding 2,4,5-trisubstituted imidazoles in excellent yields. Copyright