- Copper-Catalyzed Synthesis of Dibenzo[ b, f ]imidazo[1,2- d ][1,4]oxazepine Derivatives via a Double Ullmann Coupling Reaction
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A double Ullmann coupling reaction successfully takes place between 4,5-diaryl-2-(2-bromophenyl)-1 H -imidazoles and 2-bromophenols in the presence of Cs 2 CO 3. This procedure is catalyzed by copper(I) iodide and o -phenanthroline a
- Chen, Xin-Yi,Li, Zhuo-Huan,Liu, Jian-Quan,Wang, Xiang-Shan
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- Isocyanide Insertion-Cyclization Reaction for Imidazoisoindol-5-imine Scaffold Synthesis: A Selective Solvatochromic Fluorescent Probe for Methanol Detection
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An efficient, ligand-free, and Pd-catalyzed method for the synthesis of imidazoisoindole imine scaffolds with satisfactory yields via C-C and C-N bond formation has been developed. The synthesized scaffolds have unique potential for selective MeOH detecti
- Ahmadi, Fereshteh,Goli, Hamid Reza,Balmohammadi, Yaser,Bazgir, Ayoob
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Read Online
- Construction of trinuclear N-fused hybrid scaffolds by coupling and cyclization of 2-bromoaryl- and 2-bromovinylimidazoles with ureas under recyclable Cu/C–Al2O3 catalysis
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2-(2-Bromoaryl)- and 2-(2-bromovinyl)imidazoles are coupled and cyclized with cyclic ureas as building blocks under recyclable heterogeneous Cu/C–Al2O3 catalysis to afford a class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]imidazo[1,2-c]quinazolines and benzo[4,5]imidazo[1,2-a]imidazo[1,2-c]pyrimidines, respectively. The Cu/C–Al2O3 catalytic system could be recovered and reused three times without any loss of catalytic activity.
- Dao, Pham Duy Quang,Park, Seok Tae,Sohn, Ho-Sang,Yoon, Nam Sik,Cho, Chan Sik
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supporting information
(2022/01/13)
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- TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
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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.
- Asressu, Kesatebrhan Haile,Chan, Chieh-Kai,Wang, Cheng-Chung
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p. 28061 - 28071
(2021/09/15)
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- Facile synthesis of imidazoles by an efficient and eco-friendly heterogeneous catalytic system constructed of Fe3O4 and Cu2O nanoparticles, and guarana as a natural basis
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In this study, an efficient hybrid nanocatalyst made of guar gum (guarana, as a natural basis), magnetic iron oxide nanoparticles, and copper(I) oxide nanoparticles (Cu2O NPs) is fabricated and suitably applied for catalyzing the multicomponent (three- and four-component) synthesis reactions of imidazole derivatives. Here, an easy preparation strategy for this novel catalytic system (Cu2O/Fe3O4@guarana) is presented. Then, the application of this catalytic system for the synthesis of imidazole derivatives is precisely investigated. For this purpose, ultrasonication is introduced as an efficient and fast method. In summary, the high catalytic efficiency of Cu2O/Fe3O4@guarana nanocomposite is well demonstrated by high reaction yields obtained in the presence of a small amount of this nanocomposite, under mild conditions. Wide active surface area, substantial magnetic behavior, excellent heterogeneity, suitable stability, well reusability, and etc. have distinguished this catalytic system as an instrumental tool for facilitating the complex synthetic reactions.
- Varzi, Zahra,Esmaeili, Mir Saeed,Taheri-Ledari, Reza,Maleki, Ali
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- Facile fabrication of porous magnetic covalent organic frameworks as robust platform for multicomponent reaction
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The design of cheap yet efficient nanoporous magnetic catalysts for the environmentally benign process's widespread application is an extremely attractive, challenging chemical research field. A novel porous magnetic covalent organic framework was prepared by the condensation reaction of melamine and terephthaladehyde on the surface of 3,4-dihydroxybenzaldehyde coated magnetic Fe3O4 nanoparticles COF@Fe3O4 under hydrothermal conditions for the first time. The high surface area magnetic COF could exhibit superior catalytic activity for sustainable synthesis of trisubstituted and tetrasubstituted imidazoles and pyrroles in good to excellent yields in PEG as solvent under environmentally friendly, ambient conditions and making the overall process economical, efficient, and green. The retrievable catalyst in PEG is general and applicable to a broad substrate scope and functional group compatibility. The structure and morphology of the COF@Fe3O4 were characterized by FTIR, XRD, EDX, and SEM spectroscopy. The COF@Fe3O4 magnetic catalyst was recovered by an external magnet and used for several cycles without significant catalytic activity loss.
- Azizi, Najmedin,Heidarzadeh, Fatemeh,Farzaneh, Fezeh
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- Synthesis of Trinuclear Benzimidazole-Fused Hybrid Scaffolds by Transition Metal-Free Tandem C(sp2)?N Bond Formation under Microwave Irradiation
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2-(2-Bromoaryl)- and 2-(2-bromovinyl)benzimidazoles have been coupled and cyclized with 2-methoxy- and 2-aryloxybenzimidazoles as building blocks in the presence of a base under microwave irradiation to give a class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo[1,2-c]quinazolines and -pyrimidines, respectively, in good yields. 2-(2-Bromoaryl)- and 2-(2-bromovinyl)imidazoles also reacted with 2-methoxybenzimidazoles in the presence of base under microwave irradiation to give a class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]imidazo[1,2-c]quinazolines and -pyrimidines, respectively, in similar yields. This process seems to proceed via an initial C(sp2)-N coupling by an addition-elimination nucleophilic aromatic substitution (SNAr) and subsequent cyclization accompanied by extrusion of alcohols.
- Dao, Pham Duy Quang,Cho, Chan Sik
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p. 4088 - 4098
(2021/06/16)
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- A new nanocomposite catalyst based on clay-supported heteropolyacid for the green synthesis of 2,4,5-trisubstituted imidazoles
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Intercalation of cetyltrimethylammonium (CTA+) cations within the nanolayers of montmorillonite (MMT) clay followed by reaction with Keggin-type phosphomolybdic acid (PMo) resulted in the synthesis of (CTA)3PMo-MMT nanocomposite catalyst. The prepared nanocomposite catalyst was characterized using different physicochemical methods such as Fourier-transform infrared and inductively coupled plasma–optical emission spectroscopies, X-ray diffraction, and nitrogen adsorption–desorption (Brunauer–Emmett–Teller method) analyses. Characterization techniques demonstrated the intercalation of (CTA)3PMo species into the nanolayers of MMT. The resulting (CTA)3PMo-MMT nanocomposite catalyst efficiently catalyzed the synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions. The efficiency is due to the fact that the presence of CTA+ species makes the nanocomposite catalyst hydrophobic and facilitates the accessibility of hydrophobic reactants to active sites in the course of the reaction. High activity and selectivity were achieved in the presence of the prepared nanocomposite catalyst. The nanocomposite catalyst was readily isolated from the reaction mixture using simple filtration, washed with ethanol, and recycled five times without a major loss of activity.
- Masteri-Farahani,Ezabadi,Mazarei,Ataeinia,Shahsavarifar,Mousavi
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- A 2, 4, 5 - tri-substituted imidazole of preparation method (by machine translation)
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The invention relates to a 2, 4, 5 - tri-substituted imidazole of preparation method, the method is to be sequentially [...] or benzoins, aldehyde compounds, ammonium acetate and catalyst organic acid added in the reactor, in the 85 - 125 °C oil bath under the heating condition the reaction, after the reaction is complete to obtain a reaction mixture; the reaction mixture by washing, filtration, recrystallization after separation, to get the pure product 2, 4, 5 - tri-substituted imidazole. The present invention is simple, the production cost is low, and the yield is high, and has a good industrial application prospect. (by machine translation)
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Paragraph 0027; 0028; 0029
(2019/04/10)
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- Design and preparation of ZnS-ZnFe2O4: a green and efficient hybrid nanocatalyst for the multicomponent synthesis of 2,4,5-triaryl-1H-imidazoles
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In the present work, a new protocol was introduced for the preparation of an efficient hybrid nanocatalyst ZnS-ZnFe2O4 via the co-precipitation method as well as its application in the synthesis of 2,4,5-triaryl-1H-imidazoles derivatives starting from various aromatic aldehydes, benzil and ammonium acetate under ultrasonic irradiation in ethanol. ZnS-ZnFe2O4 was characterized by Fourier transform infrared (FT-IR) spectroscopy, energy-dispersive X-ray spectroscopy (EDS) analysis, scanning electron microscopy (SEM) image, X-ray diffraction (XRD) pattern and vibrating sample magnetometer (VSM) curve. This method has advantages such as high efficiency of the heterogeneous catalyst, the use of environmentally-friendly solvent, high yields, short reaction times and easy isolation of the products and chromatography-free purification. Our outcomes illustrated that the present nanocatalyst with nearly spherical and Cauliflower-like morphology and average particle size of 36?nm could be applied as an effective and magnetically recyclable catalyst without any significant decreasing of activity. Furthermore, the synergic effect of bimetallic Lewis acids was studied for the synthesis of imidazole derivatives.
- Varzi, Zahra,Maleki, Ali
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- Synthesis and evaluation of 2-(substituted phenyl)-4,5-diphenyl-1H-imidazole derivatives as anticonvulsant agents
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Some new 1H-imidazole derivatives were synthesized by carrying out reaction between benzil and substituted benzaldehydes and evaluated for anticonvulsant activity by maximum electroshock seizure model. The synthesized compounds were characterized by infrared, mass,1HNMR, and elemental analysis. The compounds were found to possess significant anticonvulsant effects with 3 bearing bromo substitution being the most active compound among the series.
- Maddheshiya, Ashok,Chawla, Pooja
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p. 423 - 427
(2018/09/25)
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- One-pot synthesis of multisubstituted imidazoles catalyzed by Dendrimer-PWAn nanoparticles under solvent-free conditions and ultrasonic irradiation
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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.
- Esmaeilpour, Mohsen,Javidi, Jaber,Dehghani, Farzaneh,Zahmatkesh, Saeed
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p. 163 - 185
(2017/01/14)
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- Simple, Efficient, and Convenient One-Pot Synthesis of Imidazole Derivatives in the Presence of Nanosilica-supported Imidazolium Ionic Liquid as a Catalyst
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An efficient and simple synthesis of 2,4,5-trisubstituted imidazoles is achieved by three-component cyclocondensation of benzil, aldehyde, and ammonium acetate by using nanosilica-supported imidazolium ionic liquid as a catalyst under solvent-free conditions. The key advantages of this process are high to excellent yields, short reaction time, easy work-up, and the reusability of the catalyst.
- Alinezhad, Heshmatollah,Alinezhad, Vajiheh,Mohseni Tavakkoli, Sahar
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p. 385 - 389
(2017/04/24)
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- CuI-catalyzed Sonogashira reaction for the efficient synthesis of 1H-imidazo[2,1-a]isoquinoline derivatives
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The Sonogashira reaction first, and then intra-molecular hydroamination of alkyne catalyzed by CuI/o-phen was proved to be an efficient method for the synthesis of imidazo[2,1-a]isoquinoline, phenanthro[9′,10′:4,5]imidazo[2,1-a]isoquinoline and acenaphtho[1′,2′:4,5]imidazo [2,1-a]isoquinoline derivatives in the presence of Cs2CO3.
- Gang, Ma-Yong,Liu, Jian-Quan,Wang, Xiang-Shan
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p. 4698 - 4705
(2017/07/10)
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- 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
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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.
- Esmaeilpour, Mohsen,Javidi, Jaber,Zandi, Maryam
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p. 3388 - 3398
(2015/05/20)
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- Ferric(III) nitrate supported on kieselguhr: A reusable and inexpensive catalyst for one-pot three-component synthesis of 2,4,5-trisubstituted imidazole derivatives under solvent-free conditions
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An efficient and green procedure for the synthesis of 2,4,5-trisubstituted-1H-imidazoles with various aldehydes, benzil, and ammonium acetate using a catalytic amount of ferric(III) nitrate supported on kieselguhr (Fe(NO3)3-Kie) as an active and low cost Lewis acid catalyst has been developed. The solid catalyst was easily separated from the reaction mixture and can be reused at least three times. This procedure has remarkable advantages compared to those reported in the previous literature, including high yields, cleaner reaction profiles, simple experimental and work-up procedures, and use of non-toxic or expensive catalyst. Moreover, this protocol is benign to the environment.
- Xu, Xiaowen,Li, Yiqun
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p. 4169 - 4176
(2015/06/30)
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- Synthesis of novel azole-fused quinazolines via one-pot, sequential Ullmann-type coupling and intramolecular dehydrogenative C-N bonding
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An efficient one-pot sequential procedure is described for the synthesis of novel azole-fused quinazolines through Pd/Cu co-catalyzed, Ullmann-type coupling followed by cross dehydrogenative coupling of various azoles such as 1H-imidazole, 1H-benzimidazole and 1H-1,2,4-triazole with 2-(2-bromophenyl)-1H-imidazole/benzimidazoles. The developed strategy has offered good yields (52-81%) of diverse N-fused tetra-, penta- and hexa-cyclic frameworks in a single step.
- Nandwana, Nitesh Kumar,Pericherla, Kasiviswanadharaju,Kaswan, Pinku,Kumar, Anil
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supporting information
p. 2947 - 2950
(2015/04/27)
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- Synthesis and luminescence-structure relationship of 2,4,5-triarylimidazoles
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2,4,5-Triarylimidazoles were efficiently synthesized with excellent yields (90-96%) via the one-pot concentration of benzil, aromatic aldehyde and ammonium acetate in ionic liquid [BMIM][BF4] in the present of acetic acid. The luminescence-structure relationship of products was investigated.
- Yue, Shu-Ning,Wan, Yu,Ye, Ling,Zhang, Wen-Li,Cui, Hao,Zhang, Li-Zhuo,Zhou, Qiu-Ju,Zou, Huan,Liu, Zhen-Tao,Zhao, Ling-Ling,Zhou, Sheng-Liang,Wu, Hui
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p. 6328 - 6330
(2015/02/19)
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- Synthesis of 2,4,5-triaryl and 1,2,4,5-tetraaryl imidazoles using silica chloride as an efficient and recyclable catalyst under solvent-free conditions
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An efficient solvent-free synthesis of various 2,4,5-triaryl imidazoles and 1,2,4,5-tetraaryl imidazoles has been developed using silica chloride as a heterogeneous catalyst. The present methodology offers several advantages, such as excellent yields, shorter reaction times, economic availability, and reusability of catalyst.
- Chavan, Hemant V.,Narale, Dattatraya K.
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p. 980 - 984
(2014/12/10)
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- Highly efficient one-pot synthesis of trisubstituted imidazoles under catalyst-free conditions
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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.
- Azizi, Najmadin,Dado, Nairreh,Amiri, Alireza Khajeh
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experimental part
p. 195 - 198
(2012/03/07)
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- A convenient method for the preparation of 2,4,5-triaryl imidazoles using barium chloride dispersed on silica gel nanoparticles (BaCl2-nano SiO2) as heterogeneous reusable catalyst
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A simple and eco-friendly procedure for the synthesis of 2,4,5-triaryl imidazoles by using Barium chloride dispersed on silica gel nanoparticles (BaCl2-nano SiO2) as heterogeneous reusable catalyst in high yield under thermal conditions has been described.
- Shafiee, Mohammad R.M.,Fazlinia, Abbas,Yaghooti, Najme,Ghashang, Majid
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experimental part
p. 351 - 355
(2012/08/28)
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- Efficient multi-component synthesis of highly substituted imidazoles utilizing P2O5/SiO2 as a reusable catalyst
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Phosphorus pentoxide supported on silica gel (P2O 5/SiO2) has been used as an efficient and reusable catalyst for the one-pot pseudo four-component synthesis of 2,4,5-trisubstituted imidazoles from benzil or benzoin, aldehydes, and ammonium acetate. It was also used for four-component preparation of 1,2,4,5-tetrasubstituted imidazoles from benzil or benzoin, aldehydes, primary amine, and ammonium acetate under thermal solvent-free conditions. The remarkable features of this new procedure are high conversions, cleaner reaction, simple experimental and work-up procedures and also the catalyst can be easily separated from the reaction mixture and reused several times without any loss of its activity.
- Shaterian, Hamid Reza,Ranjbar, Mohammad,Azizi, Kobra
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experimental part
p. 1635 - 1645
(2012/01/06)
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- Synthesis of highly substituted imidazoles using Bronsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate, as reusable catalyst
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Bronsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl) phosphonium toluenesulfonate, has been used as an efficient and reusable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions in excellent yields.
- Shaterian,Ranjbar,Azizi
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experimental part
p. 1120 - 1134
(2012/02/04)
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- An environmental friendly approach for the synthesis of highly substituted imidazoles using Br?nsted acidic ionic liquid, N-methyl-2-pyrrolidonium hydrogen sulfate, as reusable catalyst
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Br?nsted acidic ionic liquid, N-methyl-2-pyrrolidonium hydrogen sulfate, has been used as an efficient and reusable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under thermal solvent-free conditions in excellent yields.
- Shaterian, Hamid Reza,Ranjbar, Mohammad
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experimental part
p. 40 - 49
(2012/03/09)
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- Ionic liquid [EMIM]OAc under ultrasonic irradiation towards the first synthesis of trisubstituted imidazoles
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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.
- Zang, Hongjun,Su, Qiuhong,Mo, Yingming,Cheng, Bo-Wen,Jun, Song
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experimental part
p. 749 - 751
(2011/10/08)
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- A rapid and convenient synthesis of derivatives of imidazoles under Microwaveirradiation
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Anefficient and a quick microwave-assisted synthesis of benzimidazoles and trisubstituted imidazoles was developed. Three benzimidazoles were obtained as a result of the condensation of 1,2-phenylenediamine with carboxylic acids and acetoacetic ester without catalyst. A series of trisubstituted imidazoles were syn thesized by condensation of benzil, aromatical dehyde and ammonium acetate in the presence of glacial acetic acid.
- Zhao, Na,Wang, Yu-Lu,Wang, Jin-Ye
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p. 535 - 538
(2007/10/03)
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- Syntheses and analgesic activities of some 2-substituted-4,5-diphenyl and 1,2-disubstituted-4,5-diphenyl imidazole derivatives
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Some substituted imidazole compounds were synthesized and their analgesic activities were determined on the Swiss albino mice (25-35 g) of either sex. During the synthesis, 2-substituted-4,5-diphenyl imidazole compounds were obtained by the reaction of benzil with some substituted or nonsubstituted aldehyde derivatives, in the presence of ammonium acetate. 1- Ethyl-2-substituted-4,5-diphenyl imidazole compounds were obtained by the reaction of purified 2-substituted-4,5-diphenyl imidazole derivatives with alkyl halides in THF at the presence of NaH. All spectral and elemental analyses of the compounds were completed and their structures elucidated. Analgesic activities of the compounds were examined using the Tail-Clip method. 15a (2-p-chlorophenyl-4,5-diphenyl imidazole) and 6b (1-ethyl-2-p- hydroxyphenyl-4,5-diphenyl imidazole) derivatives were found to be more active than the others and their LD50 values were found to be greater than 100 mg/kg (i.p.).
- Isikdag,Meric
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