13682-25-2Relevant articles and documents
Organocatalyzed solvent free an efficient novel synthesis of 2,4,5-trisubstituted imidazoles for α-glucosidase inhibition to treat diabetes
Yar, Muhammad,Bajda, Marek,Shahzad, Sohail,Ullah, Nisar,Gilani, Mazhar Amjad,Ashraf, Muhammad,Rauf, Abdul,Shaukat, Ayesha
, p. 65 - 71 (2015)
A new and efficient solvent free synthesis of 2,4,5-trisubstituted imidazoles (3a-3j) was achieved by N-acetyl glycine (NAG) catalyzed three components condensation of aldehydes, benzil and ammonium acetate. Our synthetic methodology accommodated a range of various substituted alkyl and aryl aldehydes. Evaluation of α-glucosidase inhibitory activity of these imidazole derivatives revealed that most of them presented good α-glucosidase inhibition at low micro-molar concentrations. Among the synthesized compounds, compound 3c, bearing the ortho-hydroxy phenyl substituent at position 2 displayed the highest inhibitory activity with an IC50 value 74.32 ± 0.59 μM. In silico molecular docking for all compounds and computational studies of the most active compound 3c were also performed.
Highly efficient and eco-friendly synthesis of 2-alkyl and 2-aryl-4,5-diphenyl-1H-imidazoles under mild conditions
Magee, David I.,Bahramnejad,Dabiri, Minoo
, p. 2591 - 2594 (2013)
Highly efficient one-pot reactions of benzil or benzoin, ammonium acetate, and aliphatic or aromatic aldehydes were carried out in water in the presence of 1-methylimidazolium trifluoroacetate ([Hmim]TFA) under mild and green conditions. This approach can be useful for the three-component synthesis of 2-alkyl- and 2-aryl-4,5-diphenyl-1H-imidazoles in high yields. By conducting the reactions in aqueous media, the solid products were precipitated and could be isolated simply by filtration.
Living ring-opening polymerization of lactones by n-heterocyclic Olefin/Al(C6F5)3 lewis pairs: Structures of intermediates, kinetics, and mechanism
Wang, Qianyi,Zhao, Wuchao,He, Jianghua,Zhang, Yuetao,Chen, Eugene Y.-X.
, p. 123 - 136 (2017)
The strong Lewis acid Al(C6F5)3, in combination with a strong Lewis base N-heterocyclic olefin (NHO), cooperatively promotes the living ring-opening (co)- polymerization of lactones, represented by δ-valerolactone (δ-VL) and ?-caprolactone (?-CL) in this
Benzethonium Chloride Catalyzed One Pot Synthesis of 2,4,5-trisubstituted Imidazoles and 1,2,4,5-tetrasubstituted Imidazoles in Aqueous Ethanol as a Green Solvent
Parthiban,Joel Karunakaran
, p. 3004 - 3015 (2019/01/05)
A simple, efficient procedure has been developed using N-cationic surfactant namely Benzethonium chloride (BzthCl, 10 mol%) as novel catalyst for the synthesis of 2,4,5-trisubstituted imidazoles by condensation of aldehyde, ammonium acetate and benzil usi
Synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in water using p-dodecylbenzenesulfonic acid as catalyst
Das, Biswanath,Kashanna, Jajula,Kumar, Rathod Aravind,Jangili, Paramesh
, p. 223 - 226 (2013/07/27)
2,4,5-Trisubstituted imidazoles have been synthesized by treatment of benzil with aldehydes and ammonium acetate in water under reflux in the presence of p-dodecylbenzenesulfonic acid as catalyst. The same reaction using an additional amine affords 1,2,4,
Metal-free, acid-promoted synthesis of imidazole derivatives via a multicomponent reaction
Chen, Chung-Yu,Hu, Wan-Ping,Yan, Pi-Cheng,Senadi, Gopal Chandru,Wang, Jeh-Jeng
supporting information, p. 6116 - 6119 (2014/01/17)
An expedient and metal-free synthetic route has been developed for the construction of tri- and tetrasubstituted imidazole derivatives via acid promoted multicomponent reaction methodology. The reaction proceeded smoothly with a range of functionalities to produce the imidazole scaffolds in good to excellent yields.
Catalytic procedures for multicomponent synthesis of imidazoles: Selectivity control during the competitive formation of tri- and tetrasubstituted imidazoles
Kumar, Dinesh,Kommi, Damodara N.,Bollineni, Narendra,Patel, Alpesh R.,Chakraborti, Asit K.
experimental part, p. 2038 - 2049 (2012/08/27)
The catalytic potential of different fluoroboric acid-derived catalyst systems viz. aq HBF4, solid supported HBF4, metal tetrafluoroborates (inorganic salts), solid supported metal tetrafluoroborates, and tetrafluoroborate based ionic liquids (organic salts) were investigated for the three component reaction (3-MCR) of 1,2-diketone, aldehyde, and ammonium salts to form 2,4,5-trisubstituted imidazoles and the four component reaction (4-MCR) involving 1,2-diketone, aldehyde, amine and ammonium acetate to form 1,2,4,5-tetrasubstituted imidazoles. The HBF4-SiO2 was found to be the stand out catalyst for both the 3-MCR and 4-MCR processes. The next most effective catalysts are LiBF4 and Zn(BF4) 2 to form 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles via the 3-MCR and 4-MCR, respectively. This is the first report on the unaddressed issue of competitive formation of 2,4,5-trisubstituted imidazole during the 4-MCR involving 1,2-diketone, aldehyde, amine and ammonium acetate and highlights the influence of the catalyst systems in controlling the selective formation of tetra substituted imidazole. The metal salt of weak protic acids drive selectivity towards tetra substituted imidazole in the order tetrafluoroborates > perchlorates > triflates. The catalytic potency of tetrafluoroborates was in the order Zn(BF4)2 > Co(BF4)2 > AgBF4 ≈ Fe(BF 4)2 > NaBF4 ≈ LiBF4 ≈ Cu(BF4)2. The developed protocols worked well for different diketones, various aryl, heteroaryl, and alkyl aldehydes and in the case of the preparation of 1,2,4,5-tetrasubstituted imidazoles different amines can be used. The effectiveness of different ammonium salts as nitrogen source has been investigated and ammonium acetate is proved to be the best. The HBF4-SiO2 is recyclable for five consecutive uses without significant loss of catalytic activity. The Royal Society of Chemistry 2012.
Highly efficient one-pot synthesis of trisubstituted imidazoles under catalyst-free conditions
Azizi, Najmadin,Dado, Nairreh,Amiri, Alireza Khajeh
experimental part, p. 195 - 198 (2012/03/07)
Operationally simple, atom economical, and scalable synthesis of 2,4,5-trisubstituted imidazoles from benzil, aldehydes, and ammonium acetate is shown to proceed readily in methanol with high yield. The scope of the reaction is quite broad; a variety of aromatic and aliphatic activated and unactivated aldehydes have all been shown to be viable substrates for this reaction. Excellent yields and purity were obtained by washing the products with hot ethanol.
Efficient synthesis of 5-substituted 2,3-diphenyl and 5-substituted 1-aryl-2,3-diphenyl imidazoles using polyethylene glycol
Das, Biswanath,Sudhakar, Chithaluri,Srinivas, Yallamalla
experimental part, p. 2667 - 2675 (2010/10/21)
Treatment of benzoin with an aldehyde and NH4OAc in polyethylene glycol (PEG-400) under reflux afforded a 5-substituted 2,3-diphenyl imidazole while the same reaction along with an additional aniline produced 5-substituted 1-aryl 2,3-diphenyl imidazole. No any catalyst or solvent was required to carry out this conversion, and the imidazoles were formed in excellent yields.
l-Proline: an efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles
Samai, Subhasis,Nandi, Ganesh Chandra,Singh, Pallavi,Singh
experimental part, p. 10155 - 10161 (2010/02/27)
A simple highly versatile and efficient synthesis of 2,4,5-trisubstituted imidazoles is achieved by three-component cyclocondensation of 1,2-dicarbonyl compound, aldehyde and ammonium acetate using l-proline as a catalyst in methanol at moderate temperature. To explore the utility of this method 1,2,4,5-tetrasubstituted imidazoles were also synthesized. The key advantages of this process are high yields, cost effectiveness of catalyst, easy work-up and purification of products by non-chromatographic methods.
