53458-00-7Relevant academic research and scientific papers
TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
Asressu, Kesatebrhan Haile,Chan, Chieh-Kai,Wang, Cheng-Chung
, p. 28061 - 28071 (2021/09/15)
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.
Metal chloride hydrates as lewis acid catalysts in multicomponent synthesis of 2,4,5-triarylimidazoles or 2,4,5-triaryloxazoles
Marques, Marcelo V.,Ruthner, Marcelo M.,Fontoura, Luiz A. M.,Russowsky, Dennis
experimental part, p. 171 - 179 (2012/03/26)
A series of nine metal chloride hydrates (ZnCl2.2H2O, SnCl2.2H2O, CdCl2.2H2O, MnCl 2.4H2O, CoCl2.6H2O, SrCl 2.6H2O, NiCl2.6H2O, CrCl 3.6H2O and CeCl3.7H2O) was investigated as mild and inexpensive Lewis acid catalysts to promote the multicomponent synthesis of triarylimidazoles. Reactions starting from benzil showed the best results when SnCl2.2H2O was used, while for benzoin as the starting material, CeCl3.7H2O was more efficient. All reactions were performed in EtOH as solvent. These catalysts were also successfully employed in the synthesis of triaryloxazoles.
Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles
Lombardino,Wiseman
, p. 1182 - 1188 (2007/10/04)
A number of trisubstituted imidazoles were made and several found to be potent antiinflammatory agents when examined in the carrageenan rat paw edema test. The antiinflammatory activity of these compounds is retained in adrenalectomized rats. Unlike many previously reported antiinflammatory agents, these compounds are extremely weak acids pK[a] ≥ 11) and are therefore not ionized at physiological pH. One compound, 4,5 bis (4 methoxyphenyl) 2 trifluoromethylimidazole (flumizole), is more potent than indometacin in the rat paw edema test and, in contrast to some related compounds, does not cause photosensitization in mice.
