84203-09-8Relevant articles and documents
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.
Urea-Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel
Higuera, Natalia López,Pe?a-Solórzano, Diana,Ochoa-Puentes, Cristian
, p. 225 - 229 (2019/01/14)
The low-melting mixture urea-ZnCl 2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1 H -imidazoles or 2-aryl-1 H -phenanthro[9,10- d ]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.
One-pot synthesis of polysubstituted imidazoles from arylaldehydes in water catalyzed by nhc using microwave irradiation
Wu, Lei,Jing, Xiaobi,Zhu, Hongxiang,Liu, Yinlin,Yan, Chaoguo
, p. 1204 - 1207 (2013/03/28)
A simple, high yielding synthesis of tri (3a-i) and tetrasubstituted (4a-g) imidazols from aldehydes is described. The cornerstone of this methodology involves the condensation of NH4OAc, substituted aldehydes, and benzoin, which is synthesized in situ from aldehydes catalyzed by N-heterocyclic carbine (NHC), under microwave irradiation in water to afford trisubstituted imidazoles (3a-i). If arylamine is added in the solution, tetrasubstituted imidazoles (4a-g) can be obtained. Lepidilines B and trifenagrel are also synthesized in high yield using this procedure. All the experiment deta are in agreement with the literature.