73445-46-2

Usage

InChI:InChI=1/C23H18F2N2O2/c1-28-17-8-3-14(4-9-17)21-22(15-5-10-18(29-2)11-6-15)27-23(26-21)19-12-7-16(24)13-20(19)25/h3-13H,1-2H3,(H,26,27)

Upstream product

• 136123-73-4 2-(2,4-difluorophenyl)-4-hydroperoxy-4,5-bis(4-methoxyphenyl)imidazole 
• 1550-35-2 2,4-difluorobenzaldehyde 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 
• 5471-63-6 1,3-diphenylisobenzofuran 

Downstream Products

• 136123-73-4 2-(2,4-difluorophenyl)-4-hydroperoxy-4,5-bis(4-methoxyphenyl)imidazole 

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.

Peroxide chemistry of triaryl-substituted imidazoles. Fenflumizole, a non-steroidal, anti-inflammatory agent.

Fenflumizole, [2-(2,4-difluorophenyl)4,5-bis(4-methoxyphenyl)imidazole] is a nonsteroidal, anti-inflammatory analgesic. It reacts quantitatively with 1O2 forming 2-(2,4-difluorophenyl)-4-hydroperoxy-4,5-bis(4-methoxyphenyl)imidazole in a reversible reaction. In ethanol solution at ambient temperatures, the peroxide regenerates parent fenflumizole and 1O2 together with minor quantities of other products. The structures of those products point to the intermediacy of a 1,3-endoperoxide and a dioxetane. These observations may be relevant to the biological activity of fenflumizole.

Fluorine containing 2,4,5-triphenylimidazoles

Fluorosubstituted benzaldehydes are condensed with anisil and ammonium acetate to yield the corresponding 2-(fluorosubstituted phenyl)-4,5-bis(4-methoxyphenyl)imidazoles. Alternatively fluorosubstituted benzaldehydes are condensed with anisil monoxime and ammonium acetate to yield the corresponding 2-(fluorosubstituted phenyl)-4,5-bis(4-methoxyphenyl)-imidazole-3-oxides which can subsequently be reduced to yield the corresponding 2-(fluorosubstituted phenyl)-4,5-bis(4-methoxyphenyl)imidazoles. These imidazoles have interesting pharmacological properties.