- A green and simple method for the synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives using acidic ionic liquid as an effective and recyclable catalyst under ultrasound
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Abstract: In the current work, an acidic ionic liquid ([{(IMC)-4-OMBH}BIM][HSO4]3) has been utilized as an effective and recyclable catalyst for the synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives with high yields under optimal reaction conditions and ultrasound irradiation. Important features of the new catalyst are facile synthesis, cheap reagents and successful reuse for many times. What makes the present method an effective contribution in the field of synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives is the fact that it can be described as environmentally friendly, economical, short reaction time, possible recover of the catalyst, simple workup, safer and mild reaction conditions. Graphic abstract: [Figure not available: see fulltext.].
- Ahmed, N. Sh.,Hanoon
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- 4-(4,5-Diphenyl-1H-imidazole-2-yl)-N,N-dimethylaniline-Cu(II) complex, a highly selective probe for glutathione sensing in water-acetonitrile mixtures
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The imidazole derivative 4-(4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline (probe 1) formed a highly coloured and non-emissive 1:1 stoichiometry complex with Cu(II) in water-acetonitrile 1:1 (v/v) solutions. Among all the amino acids (Lys, Val, Gln, L
- Okda, Hazem Essam,El Sayed, Sameh,Ferreira, Rosa C.M.,Costa, Susana P.G.,Raposo, Manuela M.,Martínez-Má?ez, Ramón,Sancenón, Félix
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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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- 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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- 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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- 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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- An eco-friendly, one pot synthesis of tri-substituted imidazoles in aqueous medium catalyzed by RGO supported Au nano-catalyst and computational studies
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An eco-compatible, mild and operationally simple aqueous phase protocol for the synthesis of 2,4,5-trisubstituted imidazoles has been achieved with high substrate scope using supported Au nanoparticles. The catalyst can be recovered for the subsequent rea
- Biswas, Sudip,Das, Madhurima,Ghatak, Avishek,Sinha, Debopam
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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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- Bronsted acidic ionic liquid catalyzed an eco-friendly and efficient procedure for synthesis of 2,4,5-trisubstituted imidazole derivatives under ultrasound irradiation and optimal conditions
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Abstract: 2-[(1H-imidazol-3-ium-3-yl)methyl]-4-{bis[3-((1H-imidazol-3-ium-3-yl) methyl-(4-hydroxyphenyl]methylene}cyclohexa-2,5-dienone trihydrogen sulfate ([2-(imm)-4-{b(immh)m}c][HSO4]3), as the new Bronsted acidic ionic liquid, is effectively prepared and revealed by using FTIR, 1H NMR, SEM, EDS, XRD and mass data. Afterward, its catalytic activity was investigated for the synthesis of 2,4,5-trisubstituted imidazole derivatives via the simple reaction between different aldehydes, ammonium acetate and benzil/benzoin under ultrasound irradiation at ambient temperature and optimal conditions. The novel procedure has the advantages of high yields, easy handling, short reaction times, and being eco-friendly and economical. Moreover, the catalyst can be easily recovered for several times without any additional treatment. Graphic abstract: [Figure not available: see fulltext.].
- Hilal,Hanoon
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p. 1521 - 1538
(2019/12/02)
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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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- 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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- New phosphonium molybdate-promoted green, fast and selective catalytic procedure for the synthesis of trisubstituted imidazoles
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The compound 1,1′-(ethane,1,2-diyl)ditriphenylphosphonium hexamolybdate dimethylsulfoxide {C2H4[P(C6H5)3]2}{Mo6O19}·SO (CH3)2 (I) was prepared, and 1H-NMR, 13C-NMR, Fourier transform-infrared, differential scanning calorimetry and single crystal X-ray diffraction analysis were used to characterize the titled compound. Crystallographic data showed that compound I crystallized in the monoclinic crystal system in C2/c space group. The compound (I) was used for selective synthesis of 2,4,5-tri aryl imidazole derivatives under solvent-free conditions efficiently. Because of hindrance of the catalyst, the yields of products for aldehydes bearing para substituents are higher than the aldehydes bearing ortho substituents, and for aromatic aldehydes with meta substituents are very low.
- Salmasi, Reihaneh,Gholizadeh, Mostafa,Salimi, Alireza
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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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- 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 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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- In vitro evaluation of arylsubstituted imidazoles derivatives as antiprotozoal agents and docking studies on sterol 14α-demethylase (CYP51) from Trypanosoma cruzi, Leishmania infantum, and Trypanosoma brucei
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There is an urgent need to discover and develop new drugs to combat parasitic diseases as Chagas disease (Trypanosoma cruzi), sleeping sickness (Trypanosoma brucei), and leishmaniasis (Leishmania ssp.). These diseases are considered among the 13 most unattended diseases worldwide according to the WHO. In the present work, the synthesis of 14 arylsubstituted imidazoles and its molecular docking onto sterol 14α-demethylase (CYP51) was executed. In addition, the compounds, antiprotozoal activity against T. brucei, T. cruzi, Trypanosoma brucei rhodesiense, and Leishmania infantum was evaluated. In vitro antiparasitic results of the arylsubstituted imidazoles against T. brucei, T. cruzi, T.b. rhodesiense, and L. infantum indicated that all samples from arylsubstituted imidazole compounds presented interesting antiparasitic activity to various extent. The ligands 5a, 5c, 5e, 5f, 5g, 5i, and 5j exhibited strong activity against T. brucei, T. cruzi, T.b. rhodesiense, and L. infantum with IC50 values ranging from 0.86 to 10.23?μM. Most samples were cytotoxic against MRC-5 cell lines (1.12 50 2, SO3H, and OH groups interacts with the Fe2+ ion of the Heme group.
- Rojas Vargas, Julio Alberto,López, América García,Pérez, Yulier,Cos, Paul,Froeyen, Matheus
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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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- 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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- 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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- 2-hydroxyethylammonium formate ionic liquid grafted magnetic nanoparticle as a novel heterogeneous catalyst for the synthesis of substituted imidazoles
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Catalytic one-pot condensation of benzil, aldehyde and ammonium acetate have been successfully carried out using 2-hydroxyethylammonium formate (HEAF) grafted on a magnetic nanoparticles as a new heterogeneous catalyst. The as-prepared catalyst was charac
- Rajabzadeh, Maryam,Eshghi, Hossein,Khalifeh, Reza,Bakavoli, Mehdi
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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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- Natural bio-surfactant for pseudomulticomponent synthesis of 2-aryl-1-aryl methyl-1H-benzimidazoles
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Green chemistry emphasizes the development of environmentally benign chemical processes and technologies. Pseudo-multicomponent synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using o-phenylenediamine and aromatic aldehydes is carried out by Br?nsted acid type bio-surfactant as a catalyst. The green features of this method include the use of biodegradable catalyst obtained from renewable resource i.e. Citrus Limonium extract as bio-surfactant type Br?nsted acid, which provides a micellar media for effective cyclocondensation. The critical micellar concentration (cmc) of biosurfactant was determined by conductivity method and visualized by light microscopy measurement. Identity of all pure compounds was ascertained on the basis of FT-IR, 1H NMR and 13C NMR spectroscopic techniques.
- Morbale, Smita T.,Shinde, Sachin K.,Damate, Shashikant A.,Deshmukh, Madhukar B.,Patil, Suresh S.
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supporting information
p. 57 - 63
(2018/03/06)
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- Green Synthesis of 1,2,4,5-Tetrasubstituted and 2,4,5-Trisubstituted Imidazole Derivatives Involving One-pot Multicomponent Reaction
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Sodium lauryl sulfate has been found convenient, versatile, and eco-friendly catalyst for the synthesis of 1,2,4,5-tetrasubstituted and 2,4,5-trisubstituted imidazole derivatives by one-pot multicomponent reactions at 80°C using water as solvent. This protocol afforded advantages, that is, the metal-free reaction, purification of products by non-chromatographic method, and excellent yields.
- Bansal, Ravi,Soni, Pradeep K.,Halve, Anand K
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p. 1308 - 1312
(2018/04/25)
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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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p. 6995 - 7011
(2018/07/30)
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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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- Appel reagent as novel promoter for the synthesis of polysubstituted imidazoles
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We present an efficient method for the synthesis of polysubstituted imidazoles in the presence of Appel reagent (Ph3P/CCl4). Tri-substituted imidazoles is synthesized via condensation of aldehydes, benzil and ammonium acetate, and tetra-substituted imidazole is prepared via condensation of aldehydes, benzil, ammonium acetate and primary amines. These protocols allow the simple preparation of the desired products using readily available reagent instead of complex, expensive and toxic reagents under mild reaction conditions in excellent yields.
- Khoshneviszadeh, Mehdi,Mahdavi, Mohammad
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p. 343 - 352
(2018/05/07)
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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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- 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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- 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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- 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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- 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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- A practical and green approach towards synthesis of multisubstituted imidazoles using boric acid as efficient catalyst
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An efficient one-pot, cyclocondensation of ammonium acetate, 1,2-diphenyl ethanedione, aromatic aldehyde or arylamine, and catalyzed by boric acid is achieved to form multisubstituted imidazole derivatives. Boric acid as green property is harmless to the
- Zhang, Feifei,Gao, Qi,Chen, Bang,Bai, Yinjuan,Sun, Wei,Lv, Dongxu,Ge, Man
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supporting information
p. 786 - 789
(2016/05/09)
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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 mechanistic study of carbonyl activation under solvent-free conditions: Evidence drawn from the synthesis of imidazoles
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Syntheses of various imidazoles and their derivatives, imidazole N-oxides and 1-hydroxyimidazole 3-oxides, from sterically different dicarbonyl moieties provided insights into the self-catalytic effect of the condensed phase reactions of carbonyl compounds. The self-catalytic activity in solvent-free multi-component syntheses was investigated using a combination of methods viz., reactivity, spectroscopy and theory. While IR spectroscopic studies revealed that reacting molecules were polarised in bulk, quantum mechanical calculations of associated HCHO monomers suggest an increase in the average dipole moment of each monomer and provide evidence for the presence of cooperative effects. A comparative study of the kinetics of un-catalysed and catalysed reactions with the help of HPLC provided insights into the mechanism.
- Pradhan, Kiran,Tiwary, Bipransh Kumar,Hossain, Mossaraf,Chakraborty, Ranadhir,Nanda, Ashis Kumar
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p. 10743 - 10749
(2016/02/05)
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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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- Multi-component synthesis of highly substituted imidazoles catalyzed by nanorod vanadatesulfuric acid
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Nanorod vanadatesulfuric acid (VSA NRs), as a recyclable and eco-benign catalyst, was used for one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles using aldehydes, benzil, benzoin or 9,10-phenanthrenequinone and ammonium acetate or aniline under solvent-free conditions providing high to excellent yields. VSA is easily prepared by a simple reaction of chlorosulfonic acid and sodium metavanadate in high purity. As compared with the conventional procedures, the present protocol offers several advantages such as simplicity of procedure, short reaction time, high yields, easy workup, recoverability and reusability of the catalyst and simple purification of the products.
- Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Abdizadeh, Tooba
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p. 1491 - 1499
(2015/09/15)
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- 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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p. 3497 - 3505
(2015/06/08)
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- Tributylhexadecylphosphonium bromide: An efficient reagent system for the one-pot synthesis of 2,4,5-trisubstituted imidazoles
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The reaction of benzil, an aromatic aldehyde, and ammonium acetate in ethanol at reflux in the presence of tributylhexadecylphosphonium bromide as catalyst affords a 2,4,5-trisubstituted imidazole. The present methodology offers several advantages over the literature methods, including excellent yields, shorter reaction times, environmentally benign milder reaction conditions, cost-effectiveness of catalyst, easy workup, and purification of products by nonchromatographic methods.
- Heidari, Mohammad,Rezaei, Mohsen,Badri, Rashid
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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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- Shape-dependent catalytic activity of Fe3O4 nanostructures under the influence of an external magnetic field for multicomponent reactions in aqueous media
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High-quality and high-active one-dimensional (1-D) Fe3O4 nanostructures were synthesized via an external magnetic field (EMF) at the intensity range 0-526 μT in aqueous solution, without using any surfactant and organic solvent at room temperature. Characterization of the products was carried out using scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction spectroscopy (XRD), Fourier transform infrared spectrophotometry (FT-IR), a laser particle size analyzer, surface area (Brunauer-Emmett-Teller, BET), and vibrating sample magnetometer (VSM). The results show that EMF at a critical adjusted intensity has a great influence on the structural features such as the morphology, particle size, surface pore size distribution, and magnetic properties of the Fe3O4 nanostructure. The morphology changed from peg-like network structures to needle-like cage structures by an exposure synthesis treatment with EMF at an intensity of 362 μT. The catalytic activity of two nanostructures prepared in the presence and absence of EMF were compared in a tricomponents reaction (TCR) for the synthesis of trisubstituted imidazoles under electromagnetic irradiation. The best results were obtained for the catalyst produced in the presence of EMF while the tricomponent reaction was carried out in the absence of EMF. This EMF condition was used for the preparation of a series of alkyl-, aryl-, and heteroaryl-substituted imidazoles from the corresponding benzoin and benzil in aqueous solution as green reaction conditions. It was found that the catalyst can be efficiently recycled and reused for several repeating cycles without significant loss of catalytic activity.
- Rafiee,Joshaghani,Ghaderi-Shekhi Abadi
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p. 74091 - 74101
(2015/09/15)
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- Perlite: An inexpensive natural support for heterogenization of HBF4
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Nano-perlite-fluoroboric acid (n-PeFBA) has been synthesized by immobilization of HBF4 on perlite to produce an efficient green heterogeneous reusable solid acid catalyst. The catalyst was characterized by (FE-SEM, EDX, BET and BJH). This catalyst was employed to prepare biologically important 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles with high yields and selectivities. Advantages of solid acid include: low cost, facile handling, simple preparation, high stability, reusability and low toxicity. The catalyst could be recovered and reused for several runs without deterioration in catalytic activity.
- Kolvari, Eskandar,Koukabi, Nadiya,Hosseini, Maliheh M.,Khandani, Zeinab
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p. 36828 - 36836
(2015/05/05)
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- (Carboxy-3-oxopropylamino)-3-propylsilylcellulose as a novel organocatalyst for the synthesis of substituted imidazoles under solvent-free conditions
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(Carboxy-3-oxopropylamino)-3-propylsilylcellulose (COPAPSC), a novel organocatalyst, has been prepared by a synthesis grafting of -COOH functionalized organosilanes on a cellulose using surface hydroxyl groups as anchor points. The -CO2H group-functionalized cellulose was synthesized via the consecutive surface functionalization with 3-aminopropyltriethoxysilane (3-APTES) followed by the condensation of the surface -NH2 groups with succinic anhydride. COPAPSC is used as a catalyst for the synthesis of tri- and tetra-substituted imidazoles from the reaction of benzil, aromatic aldehydes, ammonium acetate, and amines under solvent-free conditions. The key advantages of this process are high yields, easy work-up, purification of products by non-chromatographic methods and the reusability of the catalyst.
- Salimi, Mehri,Nasseri, Mohammad Ali,Chapesshloo, Tayyebeh Daliran,Zakerinasab, Batol
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p. 33974 - 33980
(2015/04/27)
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- An efficient green MCR protocol for the synthesis of 2,4,5-trisubstituted imidazoles by Selectfluor under ultrasound irradiation
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A simple, efficient and eco-friendly procedure has been developed using Selectfluor (15% mol) as a novel catalyst under ultrasound irradiation and solvent-free conditions for the synthesis of 2,4,5-triaryimidazole by a three-component, one-pot condensation of benzil, aryl aldehydes and ammonium acetate. The present methodology offers several advantages such as excellent yields, shorter reaction times (10-15 min) and environmentally benign milder reaction conditions and easy work-up.
- Heravi, Mohammad Reza Poor,Vessally, Esmaeil,Behbehani, Gholam R. Rezaei
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p. 146 - 150
(2014/03/21)
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- Catalytic activity of Cu nanoparticles supported on Fe3O 4-polyethylene glycol nanocomposites for the synthesis of substituted imidazoles
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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
- Zarnegar, Zohre,Safari, Javad
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p. 4555 - 4565
(2014/11/07)
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- Design and Optimization of Ecofriendly One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles by Three-Component Condensation Using Response Surface Methodology
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Phase-transfer-catalyzed, highly versatile, and high-yielding protocol for the synthesis of 2,4,5-triaryl-1H-imidazoles was developed through response surface methodology (RSM). The effects of different solvents, reaction paths, and phase-transfer catalys
- Kumar, T. Durai Ananda,Yamini,Subrahmanyam,Satyanarayana
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p. 2256 - 2268
(2014/07/07)
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- Synthesis and studies of electrochemical properties of lophine derivatives
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A versatile series of lophine (2,4,5-triphenyl-1H-imidazole) derivatives (1-13) were synthesized and characterized using melting point investigation, Fourier transform infrared spectroscopy (FTIR), Liquid Chromatography-Mass Spectrometry (LC-MS), and sup
- Hariharasubramanian,Ravichandran, Y. Dominic
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p. 54740 - 54746
(2015/02/05)
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- Bronsted acid ionic liquid [Et3NH][HSO4] as an efficient and reusable catalyst for the synthesis of 2,4,5-triaryl-1H- imidazoles
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A simple and efficient procedure for synthesis of 2,4,5-triaryl-1H- imidazoles by one-pot three-component condensation of aromatic aldehydes, benzil and ammonium acetate under solvent-free conditions using ionic liquid [Et 3NH][HSO4] as catalyst is described. The remarkable features of this procedure are high yields, cleaner reaction profiles, use of non-toxic, easily available, cheap, recyclable catalyst, which also has an environmentally benign nature, and simple experimental and work-up procedures.
- Deng, Xiaocui,Zhou, Zhongqiang,Zhang, Aiqing,Xie, Guangyong
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p. 1101 - 1108
(2013/06/05)
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- Rapid access of some trisubstituted imidazoles from benzil condensed with aldehydes and ammonium acetate catalyzed by L-cysteine
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A simple highly versatile and efficient synthesis of 2,4,5- trisubstituted imidazole is achieved by three component cyclocondensation of benzil, substituted aromatic aldehyde and ammonium acetate by L-cysteine as organocatalyst under solvent free condition. The key advantages of this process are high yields, cost effectiveness catalyst, easy purification technique and above all environmentally benign.
- Roy,Rahman,Pramanick
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p. 153 - 159
(2013/02/25)
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