- One-Pot Synthesis of 2,4,5-Triphenyl Imidazoles from 1,2-Diols as Key Reagents
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A simple one-pot procedure for the preparation of 2,4,5-triphenyl imidazole derivatives is presented. The procedure involves the lead tetraacetate oxidation of 1,2-diols to give aldehydes in situ, which then undergo a three-component reaction with benzil and ammonium acetate to yield the imidazole derivatives.
- Jagadishbabu, Narasashetty,Shivashankar, Kalegowda
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- Zeolite ZSM-11 as a reusable and efficient catalyst promoted improved protocol for synthesis of 2,4,5-triarylimidazole derivatives under solvent-free condition
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Zeolite ZSM-11 catalyst was prepared by hydrothermal method and characterized by FTIR, XRD, SEM, HRTEM, EDS, and BET analysis techniques. The catalyst shows good catalytic activity toward synthesis of 2,4,5-triarylimidazole derivatives which is prepared b
- Dipake, Sudarshan S.,Lande, Machhindra K.,Rajbhoj, Anjali S.,Gaikwad, Suresh T.
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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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- Catalytic conversion of 2,4,5-trisubstituted imidazole and 5-substituted 1H-tetrazole derivatives using a new series of half-sandwich (η6-p-cymene)Ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazone ligands
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A new series of half-sandwich (η6-p-cymene) ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazide derivatives [Ru(η6-p-cymene)(Cl)(L)] [L = N'-(naphthalen-1-ylmethylene)thiophene-2-carbohydrazide (L1), N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide (L2) and N'-(pyren-1-ylmethylene)thiophene-2-carbohydrazide (L3)] were synthesized. The ligand precursors and their Ru(II) complexes (1–3) were structurally characterized by spectral (IR, UV–Vis, NMR and mass spectrometry) and elemental analysis. The molecular structures of the ruthenium(II) complexes 1–3 were determined by single-crystal X-ray diffraction. All complexes were used as catalysts for the one-pot three-component syntheses of 2,4,5-trisubstitued imidazole and 5-substituted 1H-tetrazole derivatives. The catalytic studies optimized parameters as solvent, temperature and catalyst. The catalysts revealed very active for a broad range of aromatic aldehydes presenting either electron attractor or electron donor substituents and, although less active, moderate to high activities were observed for alkyl aldehydes.
- Vinoth, Govindasamy,Indira, Sekar,Bharathi, Madheswaran,Archana, Govindhasamy,Alves, Luis G.,Martins, Ana M.,Shanmuga Bharathi, Kuppannan
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- 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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p. 4083 - 4100
(2021/06/25)
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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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- Simple practical method for synthesis of trisubstituted imidazoles: an efficient copper catalyzed multicomponent reaction
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A rapid practical process has been developed for synthesis of 2,4,5-trisubstituted-imidazoles in excellent yields up to 95% from readily available starting materials. In this CuI catalyzed synthesis, trisubstituted imidazoles were afforded in short reaction times, wherein the substrate scope is well explored with benzoin as well as benzil reacting with different aldehydes in the presence of ammonium acetate as the nitrogen source.
- Kadu, Vikas D.,Khadul, Siddheshwar P.,Kothe, Gokul J.,Mali, Ganesh A.
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p. 21955 - 21963
(2021/07/02)
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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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- Facile synthesis of imidazoles by an efficient and eco-friendly heterogeneous catalytic system constructed of Fe3O4 and Cu2O nanoparticles, and guarana as a natural basis
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In this study, an efficient hybrid nanocatalyst made of guar gum (guarana, as a natural basis), magnetic iron oxide nanoparticles, and copper(I) oxide nanoparticles (Cu2O NPs) is fabricated and suitably applied for catalyzing the multicomponent (three- and four-component) synthesis reactions of imidazole derivatives. Here, an easy preparation strategy for this novel catalytic system (Cu2O/Fe3O4@guarana) is presented. Then, the application of this catalytic system for the synthesis of imidazole derivatives is precisely investigated. For this purpose, ultrasonication is introduced as an efficient and fast method. In summary, the high catalytic efficiency of Cu2O/Fe3O4@guarana nanocomposite is well demonstrated by high reaction yields obtained in the presence of a small amount of this nanocomposite, under mild conditions. Wide active surface area, substantial magnetic behavior, excellent heterogeneity, suitable stability, well reusability, and etc. have distinguished this catalytic system as an instrumental tool for facilitating the complex synthetic reactions.
- Varzi, Zahra,Esmaeili, Mir Saeed,Taheri-Ledari, Reza,Maleki, Ali
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- 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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- 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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- 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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- 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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- NiO nanocomposites/rGO as a heterogeneous catalyst for imidazole scaffolds with applications in inhibiting the DNA binding activity
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Herein, we report a facile approach to synthesize a new highly versatile heterogeneous catalyst by spontaneous aerial oxidation based on nickel oxide nanocomposites immobilized on surface-functionalized reduced graphene oxide sheets. NiO nanocomposite/red
- Kumar, Gyanendra,Kumar, Manish,Masram, Dhanraj T.,Mogha, Navin Kumar,Subodh
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supporting information
p. 1963 - 1974
(2020/02/20)
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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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- Nickel-catalyzed oxidative hydroxylation of arylboronic acid: Ni(HBTC)BPY MOF as an efficient and ligand-free catalyst to access phenolic motifs
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A straightforward and mild oxidative ipso-hydroxylation of arylboronic acids has been achieved using a simple and non-noble metal, nickel-based reusable heterogeneous catalyst Ni(HBTC)BPY MOF (HBTC = benzene-1,3,5-tricarboxylate, BPY = 4,4′-bipyridine) in the presence of benign hydrogen peroxide as an oxidant under ambient reaction condition. The Ni(HBTC)BPY MOF exhibits excellent catalytic activity towards the formation of phenols from diverse arylboronic acids within short time and can be reused up to five times without any notable loss in its activity as well as shown high functional group tolerance even in the presence of sensitive functionalities and useful to achieve hydroxyl group in heterocycles.
- Latha, Ganesapandian,Devarajan, Nainamalai,Karthik, Murugan,Suresh, Palaniswamy
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- Propyl–SO3H functionalized SBA-15: Microwave-mediated green synthesis of biologically active multi-substituted imidazole scaffolds
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Abstract: Propylsulfonic acid functionalized Santa Barbara Amorphous-15 (SBA-15–Pr–SO3H) catalyst has been synthesized using a surface modification of mesoporous SBA-15 via the one-pot co-condensation method. The synthesized SBA-15–Pr–SO3H has been characterized by peculiar characterization techniques such as small- and wide-angle XRD, SEM–EDX, TEM, TG–DTA, acidity, FT-IR, Py-FT-IR and BET surface area analysis. The catalytic activity of synthesized catalyst has been studied towards solvent-free MW irradiation for the green and rapid synthesis of multi-substituted imidazoles, [2,4,5-triphenyl-1(H)-imidazole (tri-imidazole) and 1-benzyl-2,4,5-triphenyl-1H-imidazole (tetra-imidazole)]. The SBA-15–Pr–SO3H catalyst was found to be an efficient and recyclable solid acid catalyst and this solvent-free MW protocol afforded products in good to excellent yields of both, tri and tetra imidazoles (> 95%) within shorter reaction time (3?min) at 600?W as compared to the SBA-15 and other existing protocols. The applicability of this protocol was further explored by conducting the experiments in the presence of varied solvents and substituted aldehydes to generate a library of both, tri- and tetra-imidazole scaffolds. The catalyst was found to be reusable up to several runs without loss of its catalytic activity. This report allows the rapid and scalable access to a variety of multi-substituted imidazoles using SBA-15–Pr–SO3H, as heterogeneous catalyst. Graphical abstract: SBA-15–Pr–SO3H catalyzed solvent-free MW assisted green synthesis of multi-substituted imidazoles via MCRs.[Figure not available: see fulltext.].
- Gabla, Jenifer J.,Lathiya, Dharmesh R.,Revawala, Akash A.,Maheria, Kalpana C.
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p. 1863 - 1881
(2019/01/04)
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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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- Citrate trisulfonic acid: A heterogeneous organocatalyst for the synthesis of highly substituted Imidazoles
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Citrate trisulfonic acid (CTSA), as a novel recyclable and eco-benign organocatalyst, was employed for the efficient and one-pot synthesis of trisubstituted imidazoles and tetrasubstituted imidazoles using aldehydes, ammonium acetate or aniline, and benzoin, benzyl, or 9,10-phenanthrenequinone under solvent-free conditions providing high to excellent yields. CTSA is easily prepared via the reaction of trisodium citrate and chlorosulfonic acid in high purity. Compared to the conventional procedures, the present method offers several advantages, including high yields, easy work-up, short reaction time, reusability of the catalyst, and simple purification of the products.
- Kanaani, Elham,Nasr-Esfahani, Masoud
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p. 119 - 125
(2018/09/11)
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- Synthesis of Fe3O4-DOPA-Cu Magnetically Separable Nanocatalyst: A Versatile and Robust Catalyst for an Array of Sustainable Multicomponent Reactions under Microwave Irradiation
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Abstract: Herein, we are reporting a facile route to synthesize magnetically separable copper loaded L-DOPA functionalized magnetite nanoparticles (Fe3O4-DOPA-CuNPs), which are well characterized by FT-IR, PXRD, SEM, EDAX, HRTEM, XPS, TGA and VSM techniques. This single catalyst exhibits excellent catalytic activity towards (i) synthesis of DHPMs via Biginelli reaction (ii) synthesis of imidazoles (iii) synthesis of 2-amino-4H-chromenes (iv) 1,2,3-triazole derivatives by ‘Click reaction’ under microwave irradiation (MWI). Interestingly it can be easily recovered and reused for subsequent cycles for above mentioned four important multicomponent reactions without any significant decrease in its catalytic activity. Graphical Abstract: [Figure not available: see fulltext.].
- Kumari, Mitlesh,Jain, Yachana,Yadav, Priya,Laddha, Harshita,Gupta, Ragini
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p. 2180 - 2194
(2019/05/07)
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- Direct synthesis of 2,4,5-trisubstituted imidazoles from primary alcohols by diruthenium(ii) catalysts under aerobic conditions
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Herein we report a straightforward synthetic approach to 2,4,5-trisubstituted imidazoles from readily available primary alcohols using arene diruthenium(ii) catalysts. Dinuclear arene ruthenium complexes have been synthesized and structurally characterized with the aid of analytical and spectral techniques. A library of 2,4,5-trisubstituted imidazoles was achieved with a yield up to 95% by loading 0.25 mol% of the catalyst. The present protocol is environmentally benign, which is performed under aerobic conditions and liberates water as the sole by-product.
- Sundar, Saranya,Rengan, Ramesh
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p. 1402 - 1409
(2019/02/14)
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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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- 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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- 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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- 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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- 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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- 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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- Benzethonium Chloride Catalyzed One Pot Synthesis of 2,4,5-trisubstituted Imidazoles and 1,2,4,5-tetrasubstituted Imidazoles in Aqueous Ethanol as a Green Solvent
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A simple, efficient procedure has been developed using N-cationic surfactant namely Benzethonium chloride (BzthCl, 10 mol%) as novel catalyst for the synthesis of 2,4,5-trisubstituted imidazoles by condensation of aldehyde, ammonium acetate and benzil usi
- Parthiban,Joel Karunakaran
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p. 3004 - 3015
(2019/01/05)
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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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- 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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- In silico studies, synthesis and pharmacological evaluation to explore multi-targeted approach for imidazole analogues as potential cholinesterase inhibitors with neuroprotective role for Alzheimer's disease
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Alzheimer's disease (AD) is a progressive neurodegenerative disorder with multiple factors associated with its pathogenesis. Our strategy against AD involves design of multi-targeted 2-substituted-4,5-diphenyl-1H-imidazole analogues which can interact and inhibit AChE, thereby, increasing the synaptic availability of ACh, inhibit BuChE, relieve induced oxidative stress and confer a neuroprotective role. Molecular docking was employed to study interactions within the AChE active site. In silico ADME study was performed to estimate pharmacokinetic parameters. Based on computational studies, some analogues were synthesized and subjected to pharmacological evaluation involving antioxidant activity, toxicity and memory model studies in animals followed by detailed mechanistic in vitro cholinesterase inhibition study. Amongst the series, analogue 13 and 20 are the most promising multi-targeted candidates which can potentially increase memory, decrease free radical levels and protect neurons against cognitive deficit.
- Gurjar, Archana S.,Darekar, Mrunali N.,Yeong, Keng Yoon,Ooi, Luyi
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p. 1511 - 1522
(2018/02/13)
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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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- 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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- Copper(I) complex of 1,3-DimethylBarbituric acid modified SBA-15 and its catalytic role for the synthesis of 2,3-Dihydroquinazolin-4(1H)-ones and Imidazoles
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An efficient one-pot method for synthesis of 2,3-dihydroquinazolin-4(1H)-ones and tri/tetra substituted-1H-imidazoles has been accomplished in the presence of catalytic amounts of Cu(I)-1,3-dimethylbarbituric acid modified SBA-15 as heterogeneous catalyst with good to excellent yields. The catalyst is reusable and can be applied several times without any decrease in product yield. The synthesized catalyst was characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), energy dispersive X-ray spectroscopy (EDS), thermal gravimetric analysis (TGA), N2 adsorption/desorption isotherms (BET), Fourier transform infrared spectroscopy (FT-IR) and atomic absorption spectroscopy (AAS).
- Hajjami, Maryam,Ghorbani, Farshid,Yousofvand, Zakieh
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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 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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- 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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- 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 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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- 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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- 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 0031
(2017/02/09)
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