Ionic liquid [EMIM]OAc under ultrasonic irradiation towards the first synthesis of trisubstituted imidazoles

Abstract

The ionic liquid 1-ethyl-3-methylimidazole acetate ([EMIM]OAc) was found to be a mild and effective catalyst for the efficient, one-pot, three-component synthesis of 2-aryl-4,5-diphenyl imidazoles at room temperature under ultrasonic irradiation. This procedure has many obvious advantages compared to those reported in the previous literatures, including avoiding the use of harmful catalysts, reacting at room temperature, high yields, simplicity of the methodology.

Microwave-assisted synthesis of nitrogen-containing heterocycles

“…Imidazole derivatives have attracted considerable attention in recent years as these are endowed with a wide range of pharmaceutical activities [6,37]. The application of imidazoles as 1,3-disubstituted imidazole salts as ionic liquids are also well known [37].…”

“…The application of imidazoles as 1,3-disubstituted imidazole salts as ionic liquids are also well known [37]. Classically, imidazoles have been synthesized by various methods [38][39][40][41].…”

Nano Copper Ferrite Catalyzed Sonochemical, One-Pot Three and Four Component Synthesis of Poly Substituted Imidazoles

“…Later on a first, simple and convenient synthetic methodology has been reported by Radziszewski and japp for the synthesis of 2,4,5-tri phenyl imidazoles by using 1,2 dicarbonyl compounds, ammonia, various aldehydes [14]. Afterward several methods have been reported for the synthesis of tri-substituted imidazoles by cyclo condensation of 1,2 dicarbonyl compounds, various aromatic aldehydes and ammonium acetate using various catalysts such as NiCl 2 •6H 2 O/Al 2 O 3 [15], MoO 3 /SiO 2 [16], Polymer supported zinc chloride [17], trichloro isocyanuric acid (TCCA) [18] under reflux conditions and glyoxalic acid as catalyst under microwave conditions [19] and Zinc (II) (tetra (4-methylphenyl)) porphyrin [20], Magnetic Fe 3 O 4 nano particles [21], Sulfamic acid functionalized magnetic nano particles SA-MNP [22], Ionic liquid (EMIM)OAc [23], Zr(acac) 4 [24], ceric ammonium nitrate [25] as catalysts under ultra sound assisted conditions. In the same way several methods have been reported for the synthesis of tetra substituted imidazoles by cyclo condensation of 1,2 dicarbonyl compounds, various aromatic aldehydes, ammonium acetate and aromatic/aliphatic amines using various catalysts such as nano TiCl 4 •SiO 2 [26] [33] as catalyst under Ultra sound irradiation.…”

Ultrasound-Promoted Synthesis of 9-Aryl-l,8-dioxo-octahydroxanthenes Using TiO2 as a Cheap and Reusable Catalyst

“…Sonochemistry involves the use of ultrasound technique to promote organic reactions. A large number of ultrasonic reactions can be carried out in higher yield, shorter reaction time or under milder conditions 2 . Ultrasound irradiation has been demonstrated as an alternative energy source for organic reactions which can be ordinarily accomplished by heating 3 .…”