Synthesis of 1-aryl-4-tosyl-5-(trifluoromethyl)-1H-imidazoles

• Published in: Journal of fluorine chemistry Vol. 163; pp. 34 - 37
• Main Authors: Bunev, Alexander S., Vasiliev, Maksim A., Statsyuk, Vladimir E., Ostapenko, Gennady I., Peregudov, Alexander S.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.07.2014; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chlorides; Condensing; Fluorine; Imidazole; Imidazoles; Isocyanides; Physical Sciences; Science & Technology; Synthesis (chemistry); Trifluoroacetimidoyl halides; Trifluoromethyl azoles; van Leusen reaction; Trifluoroacetimidoyl halides; van Leusen reaction; Imidazoles; Trifluoromethyl azoles; Isocyanides; ONE-POT SYNTHESIS; CATALYST; TETRASUBSTITUTED IMIDAZOLES; HIGHLY EFFICIENT; REARRANGEMENT; CYCLOADDITION; HETEROCYCLES; DERIVATIVES; SUBSTITUTED IMIDAZOLES; SOLVENT-FREE SYNTHESIS
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2014.04.013

•Synthesis of new series of 9 trifluoromethyl-containing imidazoles.•This method has the ability to tolerate a wide variety of substitutions.•Compounds were characterized adequately by various spectral data and CHN analysis.•Newly synthesized compounds exhibited potential biological activity. A new synthetic protocol for the synthesis of 1,4,5-trisubstituted imidazoles containing trifluoromethyl group has been developed using van Leusen reaction, which incorporates two-component condensation reaction trifluoroacetimidoyl chlorides with tosylmethylisocyanide. This protocol provides a novel and improved method for obtaining trifluoromethyl containing 1,4,5-trisubstituted imidazoles in good yields.