- Deep eutectic solvent for multi-component reactions: A highly efficient and reusable acidic catalyst for synthesis of 2,4,5-triaryl-1H-imidazoles
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Efficient synthesis of 2,4,5-trisubstituted imidazoles has been achieved by three-component cyclocondensation of benzil or benzoin, an aldehyde, and ammonium acetate by use of an acidic catalyst. The catalyst is a deep eutectic mixture of choline chloride and oxalic acid that is non-toxic and biodegradable. Crucial advantages of this process are high yields, shorter reaction times, easy work-up, purification of products by non-chromatographic methods, and reusability of the catalyst.
- Bakavoli, Mehdi,Eshghi, Hossein,Rahimizadeh, Mohammad,Housaindokht, Mohammad Reza,Mohammadi, Ali,Monhemi, Hassan
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- Pumice-modified cellulose fiber: An environmentally benign solid state hybrid catalytic system for the synthesis of 2,4,5-triarylimidazole derivatives
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In this study, we developed an instrumental hybrid catalytic system comprising cellulose fiber and volcanic pumice powder, which was applied as a suitable organic–inorganic hybrid catalyst for the synthesis of 2,4,5-triarylimidazole derivatives. High reaction yields (97%) were obtained in short reaction times (20 min) using this catalytic system. In physical terms, the high porosity of pumice provides an extremely high active surface area for electronic interactions among the components. Moreover, the most distinctive properties of this catalytic system are high biodegradability, simple separation of the catalyst, and good reusability. The natural pumice can be recovered easily using an external magnet and reused with no significant decline in the catalytic activity. The structural characteristics of this efficient catalytic system were assessed using various analytical methods.
- Gharibi, Saideh,Maleki, Ali,Taheri-Ledari, Reza,Valadi, Kobra
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- Synthesis and properties of novel reusable nano-ordered KIT-5-N-sulfamic acid as a heterogeneous catalyst for solvent-free synthesis of 2,4,5-triaryl-1H-imidazoles
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A novel silica-bonded propyl-N-sulfamic acid nanocatalyst (NHSO3H-KIT-5) supported on modified silica mesopore KIT-5 as an organic-inorganic hybrid with high specific surface area was successfully prepared. The 3-aminopropyltriethoxysilane (APTES) on KIT-5 was reacted with chlorosulfonic acid and accurately characterized by the FT-IR, XRD, SEM, EDAXS, and TGA techniques. This heterogeneous and recyclable catalyst catalyzed one pot, multicomponent condensation of benzil, aromatic aldehydes, and ammonium acetate in the presences of 0.05 g of nanocatalyst under solvent-free conditions to afford triaryl-imidazoles in excellent yields. This catalyst showed high catalytic activity under green conditions. This reaction was performed under open air conditions and required no special reaction conditions or chromatographic separation for purification.
- Mirsafaei, Razieh,Heravi, Majid M.,Ahmadi, Shervin,Hosseinnejad, Tayebeh
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- Synthesis of polymer-supported Fe3O4 nanoparticles and their application as a novel route for the synthesis of imidazole derivatives
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Abstract: Cross-linked poly(4-vinylpyridine) supported Fe3O4 nanoparticles, abbreviated as [P4-VP]-Fe3O4NPs, were easily prepared as a new magnetic polymeric catalyst and efficiently used for the synthesis of imidazole derivatives. The polymeric catalyst was characterized by using of?various techniques including field emission scanning electron microscopy, X-ray diffraction, vibrating sample magnetometry and Fourier transform infrared spectroscopy (FT-IR) techniques. According to the obtained results, good dispersion of Fe3O4 nanoparticles on the polymer-support and excellent magnetic property of the catalyst were achieved. Various methods have been reported for the synthesis of multi-substituted imidazoles by the reaction of benzil, aldehydes and amines or ammonium acetate in the presence of various catalysts. These methods have some disadvantages including long reaction times, non-reusability of the catalyst, polluted reaction conditions, effluent pollution, and low yields; therefore, we wish to report an efficient, fast, clean and green method for the synthesis of imidazole derivatives that has been developed by one-pot condensation reaction of benzil, ammonium acetate and aldehydes in the presence of [P4-VP]-Fe3O4 nanoparticles. The catalyst displayed good catalytic activity when applied for the synthesis of imidazole derivatives. Various imidazole derivatives were prepared in high to excellent yields (68–99%) with short reaction time and high purity. The present procedure offers advantages such as short reaction time, simple reaction work-up, and the polymeric catalyst can be regenerated and reused several times without significant loss of its activity. Graphical abstract: [Figure not available: see fulltext.].
- Hamidi, Zeinab,Karimi Zarchi, Mohammad Ali
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- Sodium bisulfite as an efficient and inexpensive catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from benzil or benzoin and aromatic aldehydes
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2,4,5-Triaryl-1H-imidazoles were efficiently synthesized from benzoin or benzil, ammonium acetate, and aromatic or heteroaromatic aldehydes in the presence of sodium bisulfite as catalyst. The present protocol offers significant improvements for the synthesis of 2,4,5-triaryl-1H-imidazoles with regard to yield of products, simplicity in operation, and cheap catalyst.
- Sangshetti, Jaiprakash N.,Kokare, Nagnnath D.,Kotharkar, Sandeep A.,Shinde, Devanand B.
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- MCM-41 mesoporous silica: Efficient and reusable catalyst for the synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions
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A simple, high-yielding synthesis of 2,4,5-trisubstituted imidazoles from 1,2-diketone/1,2-hydroxyketone and aldehydes in the presence of NH 4OAc is described. Under solvent-free conditions, aryl and heteroaryl substituted imidazoles are formed in yields ranging from 70 to 90%. Copyright Taylor & Francis Group, LLC.
- Heravi, Majid M.,Zakeri, Masoumeh,Haghi, Hoda
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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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- 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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- Sulfamic acid as an efficient and cost-effective catalyst for the synthesis of 2,4,5-triarylimidazoles and 2-arylphenanthrimidazoles
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A simple and efficient synthesis of 2,4,5-triarylimidazoles and 2-arylphenanthrimidazoles was developed using the onepot, three-component condensation reaction of an aromatic aldehyde, benzil or 9,10-phenanthroquinone and ammonium acetate in refluxing ethanol in the presence of the catalyst sulfamic acid. 2011 · Copyright by Walter de Gruyter.
- Peng, Hua-Nan,Peng, Xiao-Ming,Zheng, Da-Gui,Yu, Fei,Rao, Min
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- One-pot synthesis of 2,4,5-trisubstituted imidazoles using MoO 3/SiO2, an efficient and recyclable catalyst
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A simple one-pot synthesis has been developed for the synthesis of 2,4,5-trisubstituted imidazoles using an efficient and recyclable MoO 3/SiO2 solid acid catalyst by condensation of benzil or benzoin, benzaldehyde, and ammonium acetate in acetonitrile as a solvent. Using this solid catalyst, the reactions could be carried out under mild reaction conditions with very good yield of imidazoles, up to 95%. This catalyst could be recycled very easily, which makes this methodology environmentally benign.
- Bhosale, Sidhanath V.,Kalyankar, Mohan B.,Nalage, Santosh V.,Bhosale, Dattatry S.,Pandhare, Swati L.,Kotbagi, Trupti V.,Umbarkar, Shubhangi B.,Dongare, Mohan K.
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- Synthesis and characterization of a new polymeric catalyst and used for the synthesis of imidazole derivatives
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Cross-linked poly (4-vinylpyridine) supported TiCl4 abbreviated as [P4-VP]-Ti(IV) as a new polymeric catalyst was easily prepared and characterized by using the X-ray spectroscopy, EDS, mapping, TGA/DTG and FTIR techniques. This catalyst was used for synthesis of imidazole derivatives via one-pot three-component condensation reaction of benzil, ammonium acetate and aldehydes. This protocol offers advantages such as short reaction time, simple reaction work-up with reusability of catalyst. Graphic abstract: [Figure not available: see fulltext.].
- Karimi Zarchi, Mohammad Ali,Behboodi, Kazem,Mirjalili, Bibi Fatemeh
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p. 4929 - 4942
(2021/09/06)
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- One-Pot Three-Component Synthesis of 2,4,5-Triaryl-1H-imidazoles Using Mn2+Complex of [7-Hydroxy-4-methyl-8-coumarinyl] Glycine as a Heterogeneous Catalyst
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A highly efficient and simple synthesis of 2,4,5-trisubstituted imidazoles has been developed using highly reusable support‐free Mn2+complex of [7-hydroxy-4-methyl-8-coumarinyl] glycine as a heterogeneous catalyst via a one-pot three-component reaction of benzil, aldehydes and ammonium acetate as a nitrogen source. Moreover, this catalyst was characterized by various techniques such as field emission scanning electron microscope (FE-SEM), energy dispersive X-ray spectroscopy (EDX), FT-IR spectroscopy, powder X-ray diffraction (XRD), inductively coupled plasma (ICP) and thermal gravimetric analysis (TGA). Also, the catalyst is stable and could be reused for at least six times without significant loss of activity. Graphic Abstract: [Figure not available: see fulltext.]
- Aberi, Mahdi,Razavi, Seyyede Faeze,Sharghi, Hashem
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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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- Magnetic nanoparticle-supported sulfonic acid as a green catalyst for the one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions
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In this work, magnetic nanoparticle-supported sulfonic acid (γ-Fe2O3-SO3H) is used as an efficient catalyst in the synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles in a short time (40-70 min for trisubstituted imidazoles and 30-40 min for tetrasubstituted imidazoles) and high-purity products were obtained (92-98% for trisubstituted imidazoles and 94-98% for tetrasubstituted imidazoles) in simple multicomponent reactions. The structure of these products was confirmed via FT-IR and NMR. Green and recyclable catalysts, eco-friendly and solvent-free conditions, high catalytic activity, shorter reaction time, easy recovery by an external magnet, high purity, and excellent yields are some features of these reactions.
- Amoozadeh, Ali,Kolvari, Eskandar,Sakhdari, Mahnaz
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- Magnetic horsetail plant ash (Fe3O4@HA): a novel, natural and highly efficient heterogeneous nanocatalyst for the green synthesis of 2,4,5-trisubstituted imidazoles
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Horsetail plant ash (HA), as a natural source of mesoporous silica, has been prepared from the exposure of horsetail plant (Equisetum Arvense) to high temperature. In the present study, a new magnetically separable and also recoverable Fe3O4 nanoparticles were synthesized in the presence of natural horsetail plant ash (HA) as a support to result in Fe3O4@HA. FT-IR, XRD, TEM, SEM–EDX and VSM analysis were combined to characterize the morphology and structure of this novel synthesized nanocatalyst. This magnetically solid acid nanocatalyst showed an excellent catalytic activity for the synthesis of 2,4,5-trisubstituted imidazoles at room temperature in aqueous media. The procedure led to corresponding products in high to excellent yields and appropriate times. Additionally, this nanocatalyst can be easily recovered by a magnetic field and reused for six other consecutive reaction runs without noticeable loss of its catalytic efficiency. Based on this study, Fe3O4@HA is found to be an efficient, magnetically separable, recyclable, and green catalyst with natural source. Graphic abstract: In this work, horsetail plant ash was used as a natural source of mesoporous silica for the synthesis of Fe3O4@HA as a highly powerful magnetically solid acid nanocatalyst, which was fully characterized using various techniques. The activity of the newly synthesized nanocatalyst was tested for the synthesis of 2,4,5-trisubstituted imidazole derivatives.[Figure not available: see fulltext.]
- Hosseini Mohtasham, Nina,Gholizadeh, Mostafa
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p. 2507 - 2525
(2021/03/24)
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- Homoselective synthesis of 5-substituted 1H-tetrazoles and one-pot synthesis of 2,4,5-trisubstuted imidazole compounds using BNPs@SiO2-TPPTSA as a stable and new reusable nanocatalyst
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Considering the importance of tetrazole and imidazole derivatives in pharmacy, industry, and explosives, BNPs@SiO2-TPPTSA was easily prepared and used as an effective, stable, and renewable nanocatalyst for the homoselective synthesis of different 5-substituted 1H-tetrazoles and atom economic synthesis of 2,4,5-trisubstituted-1H-imidazoles in solventless conditions. BNPs@SiO2-TPPTSA was characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD), energy dispersive X-ray analysis (EDX), thermal gravimetric-differential thermal analysis (TGA-DTA), mapping, pH analysis, and Fourier transform infrared (FT-IR) techniques. Furthermore, the catalyst recycled for at least sequential five loads without a remarkable drop-in catalytic activity.
- Khodamorady, Minoo,Ghobadi, Nazanin,Bahrami, Kiumars
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- Ultrasound-assisted synthesis of NiO nanoparticles and their catalytic application for the synthesis of trisubstituted imidazoles under solvent free conditions
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The present protocol reports the ultrasound assisted synthesis of NiO nanoparticles(NPs) using benzylamine as a base and different types of cyclodextrins (CDs) as capping agents. The use of α-CD, β-CD or γ-CD leads to different morphologies of NiO NPs. In particular, NiO nanosheets obtained using β-CD as the capping agent. The synthesized NPs were characterized by FEG-SEM, TEM, XRD and EDS analysis. They showed high catalytic activity towards synthesis of different trisubstituted imidazoles under solvent free conditions. In addition, NiO NPs could be recycled and reused consecutively up to four recycle runs without much loss of their catalytic activity.
- Bhanage, Bhalchandra M.,Chaurasia, Shivkumar,Gajengi, Aravind L.,Monflier, Eric,Ponchel, Anne,Ternel, Jeremy
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- Catalytic activity of Co(II) Salen&at;KCC-1 on the synthesis of 2,4,5-triphenyl-1H-imidazoles and benzimidazoles
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The synthesis, reactions and biological properties of imidazoles and benzimidazole make up the bulk of the ring chemistry. In this study, the reaction between different types of aromatic aldehydes and ammonium acetate with diphenylethanedione, in ethanol solvent, using the Co(II) Salen complex&at;KCC-1 catalyst which is produced from Co (II) complex which is supported onto the KCC-1 was studied. The results showed that the products were synthesized in good to excellent yields. The products were identified with IR and NMR spectroscopy. Also, the catalyst was identified by FT-IR, TGA, TEM, and XRD. Finally, the catalyst was reused several times without lack of catalytic activity.
- Ali Nasseri, Mohammad,Allahresani, Ali,Naghdi, Elaheh
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- Organocatalyzed Solvent Free and Efficient Synthesis of 2,4,5-Trisubstituted Imidazoles as Potential Acetylcholinesterase Inhibitors for Alzheimer's Disease
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The catalytic potential of pyridine-2-carboxlic acid has been evaluated for efficient, green and solvent free synthesis of 2,4,5-trisubstituted imidazole derivatives 3a–3m. The compounds 3a–3m were synthesized by one pot condensation reaction of substituted aromatic aldehydes, benzil, and ammonium acetate in good to excellent yields (74–96 %). To explore the potential of these compounds against Alzheimer's disease, their inhibitory activities against acetylcholinesterase (AChE) were evaluated. In this series of compounds, compound 3m, bearing one ethoxy and a hydroxy group on the phenyl ring on 2,4,5-trisubstituted imidazoles, proved to be a potent AChE inhibitor (102.56±0.14). Structure–activity relationship (SAR) of these compounds was developed. Molecular dockings were carried out for the compounds 3m, 3e, 3k, 3c, 3a, 3d, 3j, and 3f in order to further investigate the binding mechanism. The inhibitor molecule was molecularly docked with acetylcholinesterase to further study its binding mechanism. The amino group of the compound 3m forms an H-bond with the oxygen atom of the residue (i. e., THR121) which has a bond length of 3.051 ?.
- Ashraf, Muhammad,Khan, Muhammad Asim,Liu, Xiao,Mutahir, Sadaf,Pervaiz, Sania,Tariq, Sidrah,Ullah, Islam,Zhou, Bao-Jing
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- Hexaaryl bis-imidazole photoinitiator and application thereof
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The invention discloses a hexaaryl bis-imidazole photoinitiator. The molar ratio of a red shift substituent group in all substitutable sites of the hexaaryl bis-imidazole photoinitiator is 6-16%. Whenthe photoinitiator is applied to a photosensitive resin composition, the photoinitiator is moderate in sensitivity, good in solubility and excellent in resolution ratio and developability, inverted trapezoids cannot appear during development, the photoinitiator has good hydrophilicity, the amount of sludge in a developing solution during recycling can be remarkably reduced, and the developing solution can be repeatedly and effectively used for multiple times. The invention also provides a photosensitive resin composition containing the photoinitiator, and an application of the composition.
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Paragraph 0171-0174
(2020/10/16)
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- Fe3O4/SO3H@zeolite-Y as a novel multi-functional and magnetic nanocatalyst for clean and soft synthesis of imidazole and perimidine derivatives
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In this study, SO3H@zeolite-Y was synthesized by the reaction of chlorosulfonic acid with zeolite-NaY under solvent-free conditions, which was then supported by Fe3O4 nanoparticles to give SO3H@zeolite-Y (Fe3O4/SO3H@zeolite-Y) magnetic nanoparticles. Several techniques were used to evaluate the physical and chemical characterizations of the zeolitic nanostructures. Fe3O4-loaded sulfonated zeolite was applied as a novel multi-functional zeolite catalyst for the synthesis of imidazole and perimidine derivatives. This efficient methodology has some advantages such as good to excellent yield, high purity of products, reusability of nanocatalyst, simple reaction conditions, environmental friendliness and an economical chemical procedure from the viewpoint of green chemistry.
- Kalhor, Mehdi,Zarnegar, Zohre
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p. 19333 - 19346
(2019/07/05)
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- Sulfonated-polyvinyl amine coated on Fe3O4 nanoparticles: a high-loaded and magnetically separable acid catalyst for multicomponent reactions
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Abstract: In this study, a PVAm-bearing SO3H groups/Fe3O4 nanocomposite was prepared via a simple and in situ polymerization of acrylamide onto the surface of magnetic nanoparticles without using organosilane precursors. In order to obtain amine-functionalized magnetic, Hofmann degradation was carried out. In the following, sulfonated-polyvinyl amine coated on Fe3O4 nanoparticles was prepared by covalent grafting of chlorosulfonic acid on amine groups. The introduction of polymer to the surface of magnetic nanoparticles increases the loading content with functional groups extremely. The resulting hybrid material was effectively employed as an unprecedented acid magnetic catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions. High yields, mild reaction conditions, short reaction times, operational simplicity with reusability are the notable features of the catalyst. The structure of the newly developed catalyst was characterized using TGA, FT-IR, SEM, TEM, VSM, EDX, CHNS, and XRD analysis. Magnetic separation and recycling of the catalyst for at least 8 runs is possible without any significant deterioration in catalytic activity. This work is the first report of employing PVAm as a linker for immobilizing liquid acid on a support.
- Arghan, Maryam,Koukabi, Nadiya,Kolvari, Eskandar
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p. 2333 - 2350
(2019/06/17)
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- An efficient multicomponent synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetic nanoparticle supported Lewis acidic deep eutectic solvent
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A mild and highly efficient reaction for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetically supported Lewis acidic deep eutectic solvent on magnetic nanoparticles (LADES?MNP) has been developed via one-pot multicomponent processes under solvent-free sonication. These reactions have good to excellent yields, mild conditions, and work-up simplicity. This method represents a new method for the preparation of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles. More importantly, LADES?MNP can be easily recovered by magnetic separation and reused five times without significant loss of catalytic activity.
- Nguyen, Thanh Thi,Thi Le, Ngoc-Phuong,Nguyen, The Thai,Tran, Phuong Hoang
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p. 38148 - 38153
(2019/12/03)
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- One-Pot Three-Component Synthesis of 2,4,5-Triaryl-1 H -imidazoles in the Presence of a Molecular Sieve Supported Titanium Catalyst under Mild Basic Conditions
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A series of 2,4,5-trisubstituted-imidazoles has been synthesized with good to excellent yields by the one-pot condensation reaction of 1,2-dicarbonyl compounds, benzaldehydes, and ammonium acetate in the presence of 4 ? molecular sieves modified with titanium(IV) as an efficient heterogeneous catalyst. The catalyst could be recovered easily and reused without significant loss of activity.
- Magyar, ágnes,Hell, Zoltán
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- One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc) 2 /Ce(SO 4) 2 /Bi(NO 3) 3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus-Radziszewski Reaction
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A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc) 2 /Ce(SO 4) 2 /Bi(NO 3) 3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus-Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using α-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a β-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72-88percent) under mild conditions.
- Li, Peilang,Li, Yiqun,Sun, Wei,Zhang, Mingjuan
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supporting information
p. 3221 - 3230
(2019/08/28)
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- Urea-Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel
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The low-melting mixture urea-ZnCl 2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1 H -imidazoles or 2-aryl-1 H -phenanthro[9,10- d ]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.
- Higuera, Natalia López,Pe?a-Solórzano, Diana,Ochoa-Puentes, Cristian
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supporting information
p. 225 - 229
(2019/01/14)
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- An eco-compatible pathway to the synthesis of mono and bis-multisubstituted imidazoles over novel reusable ionic liquids: An efficient and green sonochemical process
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Novel and environmentally benign ionic liquids (ILs) comprised of DABCO were successfully synthesized. These ILs were used as robust catalysts for the sonochemical one pot multi-component synthetic route for the functionalized annulated imidazoles in water with excellent yields. The present protocol scored well in terms of yield economy as compared with the conventional procedures. The merits of the current green method include simplicity, applicability, broad functional groups tolerance, clean reaction profiles, and no tedious work-up and they give high-to-quantitative yields. From the environmental viewpoint, these eco-friendly green catalysts can be effortlessly retrieved and reused at least seven successive times without substantial loss in catalytic activity.
- Ahmed Arafa, Wael Abdelgayed
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p. 16392 - 16399
(2018/05/22)
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- Cu(II) immobilized on guanidinated epibromohydrin-functionalized γ-Fe2O3@TiO2 (γ-Fe2O3@TiO2-EG-Cu(II)): A highly efficient magnetically separable heterogeneous nanocatalyst for one-pot synthesis of highly substituted imidazoles
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A simple, efficient and eco-friendly procedure has been developed using Cu(II) immobilized on guanidinated epibromohydrin-functionalized γ-Fe2O3@TiO2 (γ-Fe2O3@TiO2-EG-Cu(II)) for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles, via the condensation reactions of various aldehydes with benzil and ammonium acetate or ammonium acetate and amines, under solvent-free conditions. High-resolution transmission electron microscopy analysis of this catalyst clearly affirmed the formation of a γ-Fe2O3 core and a TiO2 shell, with mean sizes of about 10–20 and 5–10?nm, respectively. These data were in very good agreement with X-ray crystallographic measurements (13 and 7?nm). Moreover, magnetization measurements revealed that both γ-Fe2O3@TiO2 and γ-Fe2O3@TiO2-EG-Cu(II) had superparamagnetic behaviour with saturation magnetization of 23.79 and 22.12?emu g?1, respectively. γ-Fe2O3@TiO2-EG-Cu(II) was found to be a green and highly efficient nanocatalyst, which could be easily handled, recovered and reused several times without significant loss of its activity. The scope of the presented methodology is quite broad; a variety of aldehydes as well as amines have been shown to be viable substrates. A mechanism for the cyclocondensation reaction has also been proposed.
- Nejatianfar, Mahdi,Akhlaghinia, Batool,Jahanshahi, Roya
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- Facile One Pot Multi-Component Solvent-Free Synthesis of 2,4,5-Trisubstituted Imidazoles Using “Green” and Expeditious Ionic Liquid Catalyst under Microwave Irradiation
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Acetic acid functionalized poly(4-vinylpyridinium) bromide is a highly efficient and recyclable catalyst for the construction of 2,4,5-trisubstituted imidazole derivatives by a three-component condensation of benzyl with various aldehydes and ammonium acetate under solvent free conditions. The microwave initiated process leads to analytically pure compounds within 2–5 min. The advantages of this “green” methodology are cost-effectiveness, simple procedure, low energy consumption, no involvement of organic solvents, safe operation, clean reaction profile, high yields, and recyclability of the catalyst.
- Sonyanaik,Ashok,Rambabu,Ravi,Kurumanna,Madhu,Sakram
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p. 537 - 540
(2018/04/23)
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- Synthesis and characterization of amino glucose-functionalized silica-coated NiFe2O4 nanoparticles: A heterogeneous, new and magnetically separable catalyst for the solvent-free synthesis of 2,4,5–trisubstituted imidazoles, benzo[d]imidazoles, benzo[d] oxazoles and azo-linked benzo[d]oxazoles
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Amino glucose-functionalized silica-coated NiFe2O4 nanoparticles (NiFe2O4@SiO2@amino glucose) were chemically synthesized and characterized by transmission electron microscope (TEM), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), energy dispersive X-ray analysis (EDX), vibrating sample magnetometer (VSM), Zetasizer and Fourier transform infrared spectroscopy (FT-IR) instruments. NiFe2O4@SiO2@amino glucose supply an environmentally friendly procedure for the synthesis of 2,4,5-trisubstituted imidazoles through one-pot multicomponent condensation of benzil or benzoin, ammonium acetate with aryl aldehydes and for the synthesis of benzoxazoles using condensation reaction of 2-aminophenol with aryl aldehydes under solvent free condition. In the other study, this synthesized magnetically reusable catalyst was introduced as a new avenue for the synthesis of benzo[d]imidazoles using the reaction between aryl aldehydes and 1,2-diaminobenzene. These compounds were obtained in high yields and short reaction times. The catalyst could be easily recovered and reused for five cycles with almost consistent activity. Synthesized compounds were characterized by their physical constant, comparison with authentic samples, FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.
- Fekri, Leila Zare,Nikpassand, Mohammad,Shariati, Shahab,Aghazadeh, Behnaz,Zarkeshvari, Reza,Norouz pour, Nahid
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- Magnetically separable and recyclable g-C3N4 nanocomposite catalyzed one-pot synthesis of substituted imidazoles
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A green, reliable synthetic method and highly efficient one-pot three-component synthesis of 2,4,5-trisubstituted imidazoles from 1,2-diketones, aldehydes and ammonium acetate in the presence of recyclable magnetic graphitic carbon nitride nanocomposite (Fe3O4@g-C3N4) has been developed. Various imidazole derivatives were obtained in moderate to excellent yields and high purity after recrystallization from ethanol. Interestingly, the low-cost Fe3O4@g-C3N4 a nontoxic and inexpensive catalyst showed excellent recyclability using an external magnet without loss of parent catalytic activity even after ten cycles and its provides new opportunities for the truly environmental friendliness methodology.
- Ahooie, Tahereh Soleymani,Azizi, Najmedin,Yavari, Issa,Hashemi, Mohammad Mahmoudi
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p. 855 - 862
(2018/03/01)
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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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- Co(II) anchored glutaraldehyde crosslinked magnetic chitosan nanoparticles (MCS) for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles
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A simple, highly efficient and green synthesis of 2,4,5-trisubsituted and 1,2,4,5-tetrasubstituted imidazoles was developed using a novel MCS-GT@Co(II) magnetically recoverable and recyclable catalyst under refluxing conditions with ethanol as a solvent. The catalyst was prepared by immobilization of chitosan onto Fe3O4 using glutaraldehyde as crosslinker followed by Co(II) ion immobilization via cobalt acetate. The catalyst was characterized using various techniques. For organic products determination, 1H NMR, 13C NMR and Fourier transform infrared spectroscopies were used. The reaction was also tried with individual components of the catalyst, but the synergistic effect of the components in the prepared catalyst showed the highest yield and shortest reaction time.
- Singh, Harminder,Rajput, Jaspreet Kaur
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- Mixed cobalt/nickel metal–organic framework, an efficient catalyst for one-pot synthesis of substituted imidazoles
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Abstract: In the present work, a three-dimensional bimetallic metal–organic framework, [CoNi(μ3-tp)2(μ2-pyz)2] (tp?=?terephthalic acid, pyz?=?pyrazine) was applied as a highly efficient and recoverable heterogeneous catalyst. The catalyzed reaction was the one-pot three-component condensation reaction between benzil or benzoin with various substituted aromatic aldehydes and ammonium acetate to synthesize the corresponding imidazoles in solvent-free conditions and high to quantitative yields. The catalyst can be recycled at least five times without significant loss in the catalytic activity. To the best of our knowledge, 2,4,5-trisubstituted 1H-imidazoles were not previously synthesized using MOFs as heterogeneous catalyst. The structure of previously reported cobalt/nickel MOF has been confirmed by various techniques, such as X-ray diffraction, thermogravimetric analysis, Fourier transform infrared spectroscopy, field emission scanning electron microscopy, energy dispersive X-ray spectroscopy, and Brunauer–Emmett–Teller. Graphical abstract: [Figure not available: see fulltext.]
- Ramezanalizadeh, Hamed,Manteghi, Faranak
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p. 347 - 355
(2017/02/10)
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- Synthesis of silyl-protected terminal thioalkyne-substituted tetraaryl imidazoles: utilization of Ag–Fe/ZSM-5 bimetallic nanooxides for cyclocondensation of polysubstituted imidazoles
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An improved one-pot and ecofriendly approach to tri- and tetraaryl imidazoles through three- and four-component coupling reactions under neutral and solvent-less solid-phase conditions is presented. A series of nanosized Ag/metal oxide species on H–ZSM-5 support were tested in this procedure, with Ag–Fe/ZSM-5 bimetallic oxide nanoparticles exhibiting excellent catalytic activity for improved efficiency of the one-pot, multicomponent cyclocondensation reaction. The obtained bromoimidazole derivatives were converted into silyl-protected terminal alkynyl thiolate-substituted tetraaryl imidazoles by treatment with lithium 2,2,2-tris(trimethylsilyl)ethanedithioate, produced by reaction of organolithium reagent (Me3Si)3CLi with CS2 at 0?°C. These novel and stable synthetic intermediates are potential compounds for functionalization of imidazoles.
- Allahvirdinesbat, Maryam,Fozi, Mohaddeseh,Safa, Kazem D.,Alyari, Maryam,Nakhostin Panahi, Parvaneh,Niaei, Aligholi
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p. 2653 - 2668
(2017/03/22)
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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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- Caffeine-H3PO4: a novel acidic catalyst for various one-pot multicomponent reactions
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Caffeine-H3PO4 along with caffeine-HClO4 and caffeine-HNO3 have been prepared and applied for one-pot preparation of bis(indolyl) methanes, 4,4′-(arylmethylene) bis(1H-pyrazol-5-ols), 3,3′-(arylmethylene) bis(4-hydroxycoumarins), 2,4,5-trisubstituted imidazoles, 1‐amidoalkyl‐2‐naphthols, and polyhydroquinolines. The catalysts were characterized using Fourier-transform infrared (FTIR) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR), powder X-ray diffraction (PXRD) analysis, thermogravimetric analysis (TGA), and liquid chromatography (LC)–mass spectroscopy (MS) techniques. The results indicated high product yield, short reaction time, facile separation of catalyst, and easy work-up procedure, suggesting that caffeine-H3PO4 can be considered to be an efficient acidic catalyst for organic transformations.
- Saghanezhad, Seyyed Jafar,Sayahi, Mohammad Hosein,Imanifar, Iman,Mombeni, Mostafa,Deris Hamood, Sajedeh
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p. 6521 - 6536
(2017/10/06)
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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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- One-pot synthesis of 2,4,5-trisubstituted imidazole derivatives catalyzed by BTPPC under solvent-free conditions
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A simple and efficient method for one-pot synthesis of lophine derivatives (2,4,5-trisubstituted imidazoles) by using the benzyltriphenylphosphonium chloride (BTPPC), as a catalyst, under solvent-free conditions is described. BTPPC is an available and inexpensive catalyst; also, it can be easily supplied. This procedure led to the corresponding 2,4,5-trisubstituted imidazoles products in high yields.
- Alikarami, Mohammad,Amozad, Mozhgan
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p. 177 - 184
(2017/07/24)
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- Crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes: A bio-nanoreactor with extremely high activity toward click-multi-component reactions
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In the present study, we have designed a procedure for the synthesis of a bio-nanoreactor catalyst, crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes (CS NPs/MWCNT@Fe3O4), via an in situ ionotropic gelation method. The synthesized robust nanoreactor was fully characterized. Moreover, the catalytic activity was investigated towards the click-based multi-component reactions for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, trisubstituted imidazoles, and 1,2,3-triazoles in a green medium. Since the nanocatalyst can be recovered by applying an external magnetic field, which results in easy separation without filtration, and recycled several times without the loss of its significant activities, it shows admirable potential in reusable catalysis.
- Shaabani, Ahmad,Afshari, Ronak,Hooshmand, Seyyed Emad
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p. 8469 - 8481
(2017/08/14)
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- Synthesis and characterization of nano-copper ferrite as a magnetically separable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free condition
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The authors report herein, synthesis and characterization of nano-copper ferrite as a recoverable, ecofriendly, inexpensive, and readily available catalyst for efficient, simple, and green synthesis of multisubstituted imidazoles. Short reaction times, high yields, easy workup, and mild condition are the advantages of this protocol. The catalyst can be reused without evident loss of the catalytic activity. Characterization of the catalyst was performed fully by Fourier transform infrared spectra, X-ray diffraction, FESEM, electron dispersive X-ray, and vibration sampling magnetometer analyses.
- Nemati, Firouzeh,Elhampour, Ali,Bagheri Natanzi, Mahshid
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p. 666 - 671
(2017/08/10)
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- RADICAL POLYMERISATION INITIATORS FOR LIGHT-CURABLE DENTAL MATERIALS
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The invention provides a light-curable dental material comprising a polymerizable compound having at least one ethylenically unsaturated bond and a hexaaryl bisimidazole as a photopolymerisation initiator.
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Paragraph 0053; 0054
(2017/09/29)
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- Design and development of a novel cellulose/γ-Fe2O3/Ag nanocomposite: A potential green catalyst and antibacterial agent
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A cellulose/γ-Fe2O3/Ag nanocomposite is synthesized and used as a catalyst for the synthesis of trisubstituted imidazoles and α-aminonitriles. This catalytic protocol is simple, the reaction yield is very high, and the reaction time is very short. The remarkable magnetic properties of the nanocomposite permit easy separation of the catalyst from the reaction mixture without considerable loss of catalytic activity. In addition, antibacterial properties of the nanocomposite are investigated. For this purpose, S. aureus as the representative of Gram-positive bacteria and E. coli as the representative of Gram-negative bacteria are evaluated. To study the morphology and characterization of the prepared nanocomposite, X-ray diffraction patterns (XRD), energy-dispersive X-ray spectroscopy (EDX), field-emission scanning electron microscopy (FE-SEM), vibrating sample magnetometry (VSM) and thermal gravimetric analysis/differential thermal analysis (TGA/DTA) are obtained.
- Maleki, Ali,Movahed, Hamed,Paydar, Reza
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p. 13657 - 13665
(2016/02/18)
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- Ionophore silica-coated magnetite nanoparticles as a recyclable heterogeneous catalyst for one-pot green synthesis of 2,4,5-trisubstituted imidazoles
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Novel multi-SO3H functionalized strong Br?nsted acidic ionic liquid coated magnetite nanoparticles have been prepared and applied as catalyst for the synthesis of 2,4,5-trisubstituted imidazoles. The results showed that a novel catalyst was very efficient for the reaction and could be magnetically separated and reused at least 6 times with less reduction in its catalytic activity. Operational simplicity, low cost of the catalyst used, high yields, environmental friendliness, wide applicability, reusability and easy recovery of the catalyst using an external magnet are the most important features of this methodology. The catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), X-Ray diffraction analysis (XRD), field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray analysis (EDX), dynamic laser scattering (DLS) and vibrating sample magnetometry (VSM).
- Naeimi, Hossein,Aghaseyedkarimi, Dorsa
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p. 1243 - 1253
(2016/01/15)
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- Synthesis, characterization and application of Ni0.5Zn0.5Fe2O4 nanoparticles for the one pot synthesis of triaryl-1: H -imidazoles
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In this investigation, Ni0.5Zn0.5Fe2O4, as an efficient and heterogeneous catalyst, was prepared and characterized by IR, EDX, XRD and SEM analyses. Ni0.5Zn0.5Fe2O4 was successfully used for the synthesis of 2,4,5-triaryl substituted imidazoles by the one-pot, three component reaction under solvent-free conditions. Efficiency, generality, high yield, cleaner reaction profiles, ease of product isolation, short reaction times and simplicity are some advantages of this study.
- Khazaei, Ardeshir,Alavi Nik, Heidar Ali,Ranjbaran, Azam,Moosavi-Zare, Ahmad Reza
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p. 78881 - 78886
(2016/09/09)
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- A waste to wealth approach through utilization of nano-ceramic tile waste as an accessible and inexpensive solid support to produce a heterogeneous solid acid nanocatalyst: To kill three birds with one stone
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Regarding the subject of waste products/materials, recycling or reusing has had a pivotal role on account of environmental and economic reasons. As a consequence, the essential task, nowadays, can be invention of new and practical pathways to reuse or even recycle them. In this framework, until now, recycling of some waste products such as tile wastes has not been taken into consideration; so, we were prompted by the possibility of recycling tile wastes in the catalytic direction. To this end, we use them as cost-effective, available, and nontoxic support materials for the heterogenization of sulfuric acid, in order to prepare the novel nano-ceramic tile waste supported sulfonic acid catalyst (nano-ceramic tile waste-SO3H or n-CTW-SA). This solid acid catalyst was well characterized through FT-IR, XRD, FE-SEM, EDX, TEM, TGA, BET, BJH, pH analysis and Hammett acidity function. The as-prepared nano-ceramic tile waste supported sulfonic acid catalyst proved to be an active heterogeneous catalyst in multicomponent reactions (MRCs) for the rapid and efficient one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in high yields and selectivity. In comparison with some other homogeneous and heterogeneous catalysts, nano-ceramic tile waste supported sulfonic acid displayed a greater activity. Moreover, being highly stable, inexpensive, accessible, retrievable, reusable, and having low toxicity are some other beneficial points of this catalyst.
- Kolvari, Eskandar,Zolfagharinia, Somayeh
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p. 93963 - 93974
(2016/10/21)
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- A highly efficient synthesis of substituted imidazoles via a one-pot multicomponent reaction by using urea/hydrogen peroxide (UHP)
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A simple, versatile and highly efficient synthesis of 2,4,5-trisubstituted imidazoles by a condensation reaction of benzil or benzoin, aldehydes and ammonium acetate in the presence of urea/hydrogen peroxide (UHP) as a mild and efficient molecular catalyst in refluxing ethanol is described. The present methodology offers several advantages such as green protocol, inexpensive catalyst, high-to-excellent yields, and simple and easy work-up procedure.
- Maleki, Ali,Alirezvani, Zahra
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p. 3116 - 3119
(2016/11/18)
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- Doping of copper (I) oxide onto a solid support as a recyclable catalyst for acetylation of amines/alcohols/phenols and synthesis of trisubstituted imidazole
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A study of copper-mediated C-heteroatom especially C-N and C-O bond formations using simpler methodologies has been carried out. In the present work, acetylation of various substrates such as amines, phenols and alcohols; synthesis of 2,4,5-trisubstituted imidazole is done using simple and easily available starting materials. Copper (I) oxide was synthesized in situ by the reduction of Fehling's solution with glucose followed by its anchoring onto different supports like silica, HAP, basic alumina and cellulose. Comparison and contrasts between the reactivity of copper (I) oxide supported onto different supports for these reactions are made. The reactivity of copper (I) oxide seems to be largely dependent on the nature of support and the most active catalyst for a particular reaction was further characterized by different spectroscopic techniques such as FTIR, XRD, TGA, XPS, SEM, TEM and AAS. The catalysts were found to be stable, easily recyclable without any significant loss in activity. Graphical abstract: Applications of solid supported copper (I) oxides (where solid support is silica, HAP, cellulose and basic alumina) are studied for various organic transformations with special emphasis on C-N and C-O bond formation reactions.[Figure not available: see fulltext.]
- Gupta, Manjulla,Gupta, Monika
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p. 231 - 241
(2016/01/09)
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- An aqueous phase catalytic synthesis of 2, 4, 5-diaryl -1H-imidazole derivatives (by machine translation)
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The invention discloses an aqueous phase catalytic synthesis of 2, 4, 5-diaryl -1H-imidazole derivatives method, which belongs to the technical field of organic chemical synthesis. In the synthesis method benzion, aromatic aldehydes, and ammonium molar ratio of 1:1:2-5, [...] ionic liquid catalyst by the molar amount of the aromatic aldehydes 8-10%, reaction solvent volume of water (ml) (mmol) of the aromatic aldehyde mole of quantity 3-5 times, the reaction pressure is an atmospheric pressure, reflux reaction is 0.5-1h, after the reaction is ended a large number of solid precipitation, filtration, drying the filter residue obtained is recrystallized with ethanol, dried under vacuum to obtain the pure 2, 4, 5-diaryl -1H-imidazole derivatives. The invention and other acidic ionic liquid as compared with the preparation method of the catalyst, with the catalyst activity is good, use water as the green solvent, the whole reaction process is easy and simple to handle, the higher advantage of the economic benefits, which is convenient for industrial large-scale production. (by machine translation)
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Paragraph 0025
(2017/02/09)
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- Isocyanurate-based periodic mesoporous organosilica (PMO-ICS): A highly efficient and recoverable nanocatalyst for the one-pot synthesis of substituted imidazoles and benzimidazoles
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Isocyanurate bridging periodic mesoporous organosilica (PMO-ICS) was shown to be a highly active and efficient recyclable catalyst for the three-component synthesis of imidazole derivatives from benzoin, different aldehydes and ammonium acetate under mild reaction conditions in short reaction times and good to excellent yields in EtOH. Also, benzimidazole derivatives were efficiently prepared from o-phenylenediamine and different aldehydes in the presence of PMO-ICS. Moreover, the catalyst was also recovered and reused at least four times without a significant decrease in its activity. The PMO-ICS catalyst was characterized by Fourier transformer infrared (FTIR) spectroscopy, thermogravimetry analysis (TGA), powder X-ray diffraction (XRD) and nitrogen adsorption-desorption isotherm (NADI) techniques as well as field emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM). Compared to the classical methodologies, this method illustrated significant advantages including low loading of the catalyst, avoiding the use of toxic transition metals or reactive reagents for modification of the catalytic activity, short reaction times, high to excellent yields, easy separation and purification of the products, and reusability of the catalyst.
- Dekamin, Mohammad G.,Arefi, Elham,Yaghoubi, Amene
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p. 86982 - 86988
(2016/10/19)
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- ZrO2-β-cyclodextrin catalyzed synthesis of 2,4,5-trisubstituted imidazoles and 1,2-disubstituted benzimidazoles under solvent free conditions and evaluation of their antibacterial study
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A series of 2,4,5-trisubstituted imidazoles and 1,2-disubstituted benzimidazoles catalyzed by ZrO2-supported-β-cyclodextrin (ZrO2-β-CD) under solvent free conditions have been synthesized and characterized by spectral methods. The nanoparticles (ZrO2-β-CD), prepared by a simple one-pot-coprecipitation method and were characterized by PXRD, SEM, and TEM techniques. The nano (ZrO2-β-CD) particles were found to be an effective heterogeneous reusable catalyst for the effective synthesis of imidazoles and benzimidazoles under solvent free conditions and all of the synthesized derivatives were evaluated for their antibacterial activity against six bacterial strains.
- Girish, Yarabhally R.,Sharath Kumar, Kothanahally S.,Thimmaiah, Kuntebommanahalli N.,Rangappa, Kanchugarakoppal S.,Shashikanth, Sheena
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p. 75533 - 75546
(2015/09/21)
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- Graphene oxide-chitosan bionanocomposite: A highly efficient nanocatalyst for the one-pot three-component synthesis of trisubstituted imidazoles under solvent-free conditions
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In the present work, a green, rapid, convenient and eco-friendly method for the synthesis of 2,4,5-trisubstituted imidazoles is described. In this method, we used 1,2-diketone or α-hydroxy ketone, an aldehyde and ammonium acetate in the presence of graphene oxide-chitosan bionanocomposite, which acted as an efficient nanocatalyst. This protocol has many advantages such as short reaction time, high yield, easy separation of the catalyst and solvent-free condition. We used differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FT-IR) and atomic force microscopy (AFM) to confirm that the nanocomposite was formed, and FT-IR, 1H and 13C NMR analyses were performed for the confirmation of the synthesized products.
- Maleki, Ali,Paydar, Reza
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p. 33177 - 33184
(2015/04/27)
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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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