1262023-44-8Relevant articles and documents
Catalytic activity of Cu nanoparticles supported on Fe3O 4-polyethylene glycol nanocomposites for the synthesis of substituted imidazoles
Zarnegar, Zohre,Safari, Javad
, p. 4555 - 4565 (2014)
In the present study, we carried out chemical synthesis and characterization for a Fe3O4-polyethylene glycol-Cu nanocomposite (Fe3O4-PEG-Cu). Firstly, poly(ethylene glycol) was functionalized using cyanuric chlo
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.
Identification and Mechanistic Evaluation of Hemozoin-Inhibiting Triarylimidazoles Active against Plasmodium falciparum
Wicht, Kathryn J.,Combrinck, Jill M.,Smith, Peter J.,Hunter, Roger,Egan, Timothy J.
supporting information, p. 201 - 205 (2017/03/08)
In a previous study, target based screening was carried out for inhibitors of β-hematin (synthetic hemozoin) formation, and a series of triarylimidazoles were identified as active against Plasmodium falciparum. Here, we report the subsequent synthesis and testing of derivatives with varying substituents on the three phenyl rings for this series. The results indicated that a 2-hydroxy-1,3-dimethoxy substitution pattern on ring A is required for submicromolar parasite activity. In addition, cell-fractionation studies revealed uncommonly large, dose-dependent increases of P. falciparum intracellular exchangeable (free) heme, correlating with decreased parasite survival for β-hematin inhibiting derivatives.
One-pot synthesis of multisubstituted imidazoles catalyzed by Dendrimer-PWAn nanoparticles under solvent-free conditions and ultrasonic irradiation
Esmaeilpour, Mohsen,Javidi, Jaber,Dehghani, Farzaneh,Zahmatkesh, Saeed
, p. 163 - 185 (2017/01/14)
An efficient, green and eco-friendly protocol has been developed for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles via one-pot condensation reaction using Dendrimer-PWAn as catalyst under solvent-free conditions or ultrasonic irradiation in excellent yields. The reactions under conventional heating conditions were compared with the ultrasonic-assisted reactions. The operational simplicity, practicability and applicability of this protocol to various substrates make it an interesting alternative to previous procedures. The present methodology offers several advantages such as excellent yields, short reaction times, a cleaner reaction, and the absence of any tedious work-up or purification. The catalyst is easily separated from the products by filtration and also exhibits remarkable reusable activity. SEM, BET and DLS of the catalyst were also investigated after each reaction cycle.
One-pot synthesis of multisubstituted imidazoles under solvent-free conditions and microwave irradiation using Fe3O4@SiO2-imid-PMAn magnetic porous nanospheres as a recyclable catalyst
Esmaeilpour, Mohsen,Javidi, Jaber,Zandi, Maryam
, p. 3388 - 3398 (2015/05/20)
An efficient, green and ecofriendly procedure has been developed using Fe3O4@SiO2-imid-PMAn as a magnetic catalyst for a rapid and improved synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation in excellent yields. The reactions under conventional heating conditions were compared with the microwave-assisted reactions. The operational simplicity, practicability and applicability of this protocol to various substrates make it an interesting alternative to previous procedures. The present approach offers several advantages such as short reaction times, high yields, simplicity of operation, easy work-up, a cleaner reaction and ease of recovery and reusability of the catalyst using a magnetic field. Also, the nanocatalyst can be easily recovered by the application of a magnetic field and reused for the next reactions at least 5 times without distinct deterioration in catalytic activity. SEM, BET, DLS and leaching of the catalyst after each reaction cycle were investigated.
Fe3O4@chitosan nanoparticles: A valuable heterogeneous nanocatalyst for the synthesis of 2,4,5-trisubstituted imidazoles
Zarnegar, Zohre,Safari, Javad
, p. 20932 - 20939 (2014/06/09)
Chitosan-coated Fe3O4 nanoparticles (Fe 3O4@CS) were prepared simply through in situ co-precipitation of Fe2+ and Fe3+ ions via NH 4OH in an aqueous solution of chitosan and their catalytic activity was investigated in the synthesis of 2,4,5-trisubstituted imidazoles by a one-pot condensation of benzil derivatives, aryl aldehydes and ammonium acetate in EtOH. This novel method offers several advantages compared to those reported in the previous literature, including avoiding the use of harmful catalysts, easy and quick isolation of the products, excellent yields, mild and clean conditions, and simplicity of the methodology. High catalytic activity and ease of recovery using an external magnetic field are additional eco-friendly attributes of this catalytic system. This journal is the Partner Organisations 2014.
A highly efficient magnetic solid acid catalyst for synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation
Safari, Javad,Zarnegar, Zohre
, p. 740 - 746 (2013/02/22)
Fe3O4 nanoparticles were prepared by chemical coprecipitation method and subsequently coated with 3-aminopropyltriethoxysilane (APTES) via silanization reaction. Grafting of chlorosulfuric acid on the amino-functionalized Fe3O4 nanoparticles afforded sulfamic acid-functionalized magnetic nanoparticles (SA-MNPs). SA-MNPs was found to be a mild and effective solid acid catalyst for the efficient, one-pot, three-component synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation. This protocol afforded corresponding imidazoles in shorter reaction durations, and in high yields. This green procedure has many obvious advantages compared to those reported in the previous literatures, including avoiding the use of harmful catalysts, easy and quick isolation of the products, excellent yields, short routine, and simplicity of the methodology.
Zinc (II) [tetra(4-methylphenyl)] porphyrin: A novel and reusable catalyst for efficient synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation
Safari, Javad,Khalili, Shiva Dehghan,Banitaba, Sayed Hossein,Dehghani, Hossein
experimental part, p. 787 - 793 (2012/01/05)
An efficient three-component one-step synthesis of 2,4,5-trisubstituted imidazoles by condensation reaction of 1,2-diketones or a-hydroxyketones with aromatic aldehydes and ammonium acetate using Zinc (II) [tetra (4-methylphenyl)] porphyrin as a novel and reusable catalyst under ultrasound irradiation at ambient temperature is described. In this method, a-hydroxyketones as well as 1,2-diketones were converted to their corresponding 2,4,5-trisubstituted imidazoles in excellent yields. Copyright
Nanocrystalline magnesium oxide: A novel and efficient catalyst for facile synthesis of 2,4,5-trisubstituted imidazole derivatives
Safari, Javad,Khalili, Shiva Dehghan,Rezaei, Mehran,Banitaba, Sayed Hossein,Meshkani, Fereshteh
experimental part, p. 1339 - 1345 (2011/09/19)
Nanocrystalline magnesium oxide with high specific surface area has been used as a novel and efficient catalyst for an improved and rapid synthesis of biologically active 2,4,5-trisubstituted imidazoles, by three-component, one-pot condensation of 1,2-dik
