- The one-pot synthesis of 2,4,5-triaryl-imidazoles using heteropolyacids as heterogeneous and recyclable catalysts
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2,4,5-triaryl imidazoles were obtained in high yields with excellent purity from the condensation of benzaldehydes, NH4OAc and 1,2-diketone in the presence of a catalytic amount of various heteropolyacids (HPAs).
- Heravi, Majid M.,Sadjadi, Samaheh,Oskooie, Hossein A.,Hekmatshoar, Rahim,Bamoharram, Fatemeh F.
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- Bistability in an Isothermal Photochemical System. The Triphenylimidazolyl Radical Dimer in a CSTR
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Hysteresis and bistability were observed when a solution of triphenylimidazolyl radical dimer (TPID) is irradiated in a CSTR.The reactor is open to a flow of TPID and irradiated at 360 nm.The transition between the two stable states can be induced by changing either the flow rate or the incoming light flux.This bistability is believed to be the first experimental observation of a genuine chemical instability in an isothermal photochemical system.
- Lavabre, D.,Levy, G.,Laplante, J. P.,Micheau, J. C.
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- Tentative mechanism for the bistability observed during irradiation of the triphenylimidazolyl radical dimer in a CSTR
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We previously reported on the observation of a bistability when a chloroform solution of the triphenylimidazolyl radical dimer (TPID) is irradiated in a CSTR (continuous now stirred tank reactor) (J. Phys. Chem. 1988, 92, 16). In the present paper, the photochemistry of TPID in chloroform is examined in more detail and key reactions are summarized in a 6-step mechanism. Values of relevant kinetic parameters are determined and used in numerical simulations of the TPID/CHCl3 photochemistry in a CSTR. Multiple steady states are indeed observed when experimental values of the kinetic parameters arc used in the simulations. The bistability width and transition points are in good agreement with experimental results. It is suggested that the feedback mechanism responsible for the instability is of photometric origin. One of its key components is the screen effect that arises as the result of competitive absorption in multicomponent photochemical systems.
- Borderie,Lavabre,Levy,Micheau,Laplante
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- Laser flash photolysis study of triphenylimidazole
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Laser flash photolysis of the photocyclization of triphenylimidazole (TPI) in ethyl alcohol at 308 nm. indicates that the dihydrophenanthroimidazole (DHPI) intermediate is produced rapidly, has a lifetime of 0.25 ms, and returns predominantly back to triphenylimidazole. Analysis of the decay channels for this intermediate indicates two rate constants: (1) k1 = 3.3×103 s-1, associated with reversion back to triphenylimidazole and (2) k2 = 0.67×102 s-1 which is associated with the conversion of the dihydrophenanthroimidazole to the photoproduct, 2-phenyl-9,10-phenanthroimidazole. The photoproduct is readily observed as an increasing component in the biexponential fluorescence decay data. Fluorescence lifetimes for triphenylimidazole and 2-phenyl-9,10-phenanthroimidazole (PPI) in ethyl alcohol were determined to be 1.76 and 8.21 ns, respectively, with no additional components in the fluorescence decay as the photochemistry proceeds. An additional transient absorption observed in the 450 nm. region, with a lifetime of 0.7 μs, decaying faster than the dihydrophenanthroimidazole intermediate, is assigned to the triplet state of triphenylimidazole.
- Testa
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- Magnetic horsetail plant ash (Fe3O4@HA): a novel, natural and highly efficient heterogeneous nanocatalyst for the green synthesis of 2,4,5-trisubstituted imidazoles
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Horsetail plant ash (HA), as a natural source of mesoporous silica, has been prepared from the exposure of horsetail plant (Equisetum Arvense) to high temperature. In the present study, a new magnetically separable and also recoverable Fe3O4 nanoparticles were synthesized in the presence of natural horsetail plant ash (HA) as a support to result in Fe3O4@HA. FT-IR, XRD, TEM, SEM–EDX and VSM analysis were combined to characterize the morphology and structure of this novel synthesized nanocatalyst. This magnetically solid acid nanocatalyst showed an excellent catalytic activity for the synthesis of 2,4,5-trisubstituted imidazoles at room temperature in aqueous media. The procedure led to corresponding products in high to excellent yields and appropriate times. Additionally, this nanocatalyst can be easily recovered by a magnetic field and reused for six other consecutive reaction runs without noticeable loss of its catalytic efficiency. Based on this study, Fe3O4@HA is found to be an efficient, magnetically separable, recyclable, and green catalyst with natural source. Graphic abstract: In this work, horsetail plant ash was used as a natural source of mesoporous silica for the synthesis of Fe3O4@HA as a highly powerful magnetically solid acid nanocatalyst, which was fully characterized using various techniques. The activity of the newly synthesized nanocatalyst was tested for the synthesis of 2,4,5-trisubstituted imidazole derivatives.[Figure not available: see fulltext.]
- Hosseini Mohtasham, Nina,Gholizadeh, Mostafa
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p. 2507 - 2525
(2021/03/24)
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- Homoselective synthesis of 5-substituted 1H-tetrazoles and one-pot synthesis of 2,4,5-trisubstuted imidazole compounds using BNPs@SiO2-TPPTSA as a stable and new reusable nanocatalyst
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Considering the importance of tetrazole and imidazole derivatives in pharmacy, industry, and explosives, BNPs@SiO2-TPPTSA was easily prepared and used as an effective, stable, and renewable nanocatalyst for the homoselective synthesis of different 5-substituted 1H-tetrazoles and atom economic synthesis of 2,4,5-trisubstituted-1H-imidazoles in solventless conditions. BNPs@SiO2-TPPTSA was characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD), energy dispersive X-ray analysis (EDX), thermal gravimetric-differential thermal analysis (TGA-DTA), mapping, pH analysis, and Fourier transform infrared (FT-IR) techniques. Furthermore, the catalyst recycled for at least sequential five loads without a remarkable drop-in catalytic activity.
- Khodamorady, Minoo,Ghobadi, Nazanin,Bahrami, Kiumars
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- Ultrasound-assisted synthesis of NiO nanoparticles and their catalytic application for the synthesis of trisubstituted imidazoles under solvent free conditions
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The present protocol reports the ultrasound assisted synthesis of NiO nanoparticles(NPs) using benzylamine as a base and different types of cyclodextrins (CDs) as capping agents. The use of α-CD, β-CD or γ-CD leads to different morphologies of NiO NPs. In particular, NiO nanosheets obtained using β-CD as the capping agent. The synthesized NPs were characterized by FEG-SEM, TEM, XRD and EDS analysis. They showed high catalytic activity towards synthesis of different trisubstituted imidazoles under solvent free conditions. In addition, NiO NPs could be recycled and reused consecutively up to four recycle runs without much loss of their catalytic activity.
- Bhanage, Bhalchandra M.,Chaurasia, Shivkumar,Gajengi, Aravind L.,Monflier, Eric,Ponchel, Anne,Ternel, Jeremy
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- TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
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In the process of drug discovery and development, an efficient and expedient synthetic method for imidazole-based small molecules from commercially available and cheap starting materials has great significance. Herein, we developed a TMSOTf-catalyzed synthesis of trisubstituted imidazoles through the reaction of 1,2-diketones and aldehydes using hexamethyldisilazane as a nitrogen source under microwave heating and solvent-free conditions. The chemical structures of representative trisubstituted imidazoles were confirmed using X-ray single-crystal diffraction analysis. This synthetic method has several advantages including the involvement of mild Lewis acid, being metal- and additive-free, wide substrate scope with good to excellent yields and short reaction time. Furthermore, we demonstrate the application of the methodology in the synthesis of biologically active imidazole-based drugs.
- Asressu, Kesatebrhan Haile,Chan, Chieh-Kai,Wang, Cheng-Chung
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p. 28061 - 28071
(2021/09/15)
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- Fe3O4@THAM-Pd as a highly efficient magnetically recoverable nanocatalyst for facile one-pot assembly of substituted imidazoles under solvent-free conditions
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The current work has been explored an expeditious tactic toward one-pot multicomponent synthesis of 1,2,4,5-tetrasubstituted and 2,4,5-trisubstituted imidazoles using Fe3O4@THAM-Pd MNPs as an effective catalyst. With readily accessible benzil, ammonium acetate, anilines, and aromatic aldehydes as the simple starting materials, the condensation is run under solvent-free conditions to afford the target products in high yields. The other salient features of the present catalytic system are a simple work-up process, shorter reaction times, ease of preparation and handling of the catalyst, and cleaner reaction profiles. In addition, the sustainability of the methodology was checked by the investigation of the stability and reusability of the catalyst using an external magnet. The results showed that Fe3O4 @THAM-Pd MNPs can be reused for successive five runs without an appreciable decline in catalytic efficiency.
- Sanchooli Tazeh, Kazem,Heydari, Reza,Fatahpour, Maryam
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p. 1464 - 1472
(2021/09/18)
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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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- Facile fabrication of porous magnetic covalent organic frameworks as robust platform for multicomponent reaction
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The design of cheap yet efficient nanoporous magnetic catalysts for the environmentally benign process's widespread application is an extremely attractive, challenging chemical research field. A novel porous magnetic covalent organic framework was prepared by the condensation reaction of melamine and terephthaladehyde on the surface of 3,4-dihydroxybenzaldehyde coated magnetic Fe3O4 nanoparticles COF@Fe3O4 under hydrothermal conditions for the first time. The high surface area magnetic COF could exhibit superior catalytic activity for sustainable synthesis of trisubstituted and tetrasubstituted imidazoles and pyrroles in good to excellent yields in PEG as solvent under environmentally friendly, ambient conditions and making the overall process economical, efficient, and green. The retrievable catalyst in PEG is general and applicable to a broad substrate scope and functional group compatibility. The structure and morphology of the COF@Fe3O4 were characterized by FTIR, XRD, EDX, and SEM spectroscopy. The COF@Fe3O4 magnetic catalyst was recovered by an external magnet and used for several cycles without significant catalytic activity loss.
- Azizi, Najmedin,Heidarzadeh, Fatemeh,Farzaneh, Fezeh
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- 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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- 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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- Radiation-sensitive composition, pattern-forming method and radiation-sensitive acid generating agent
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A radiation-sensitive composition includes: a first polymer having a first structural unit that includes an acid-labile group; and a first compound including a metal cation and a first anion that is a conjugate base of an acid. The acid has a pKa of no greater than 0. The acid is preferably sulfonic acid, nitric acid, organic azinic acid, disulfonylimidic acid or a combination thereof. The first compound is preferably represented by formula (1). In the formula (1), M represents a metal cation; A represents the first anion; x is an integer of 1 to 6; R1 represents a σ ligand; and y is an integer of 0 to 5, and a sum: x+y is no greater than 6. The van der Waals volume of the acid is preferably no less than 2.5×10?28 m3. [AxMR1y]??(1)
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- Ruthenium(II)-Catalyzed Cross-Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2-Phenylacetophenones
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Herein, we report a direct method to synthesize 2-phenylacetophenone through a ruthenium(II)-catalyzed cross-coupling reaction between acyl and benzyl radical. The various derivatives of 2-phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward pathway to synthesize a variety of ketones bearing various functional groups.
- Chen, Yujie,Dai, Chenyang,Huang, Zhibin,Jiang, Yaqiqi,Shu, Sai,Yang, Shan,Zhao, Yingsheng
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p. 2955 - 2961
(2021/07/22)
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- One-pot cascade synthesis of α-diketones from aldehydes and ketones in water by using a bifunctional iron nanocomposite catalyst
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A new methodology for the synthesis of α-diketones was reportedviaa one-pot cascade process from aldehydes and ketones catalyzed by a bifunctional iron nanocomposite using H2O2as a green oxidant in water. The one-pot strategy showed excellent catalytic stability, comprehensive suitability of substrates and important practical utility for directly synthesizing biologically active and medicinally valuable N-heterocyclesviaan intermittent process.
- Song, Tao,Zhou, Xin,Wang, Xiaoxue,Xiao, Jianliang,Yang, Yong
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p. 1955 - 1959
(2021/03/26)
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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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- 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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- 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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- 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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- Sugar-Catalyzed Synthesis of Triarylimidazoles—An Exemplary Model of Sweet Chemistry
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Abstract: A fine, green, and efficient method has been proposed for the synthesis of2-aryl-4,5-diphenyl-1H-imidazoles usingvarious sugars such as glucose, fructose, sucrose, lactose, and maltose ascatalysts. The syntheses were carried out under very mild
- Babar, R.,Ijaz, F.,Khan, M. A.,Munawar, M. A.,Rizwan, M.,Shafqat, S. S.,Zafar, M. N.
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p. 509 - 513
(2020/04/27)
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- Visible light-emitting diode light-driven one-pot four component synthesis of poly-functionalized imidazoles under catalyst- And solvent-free conditions
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Here, we have demonstrated the visible LED light-promoted synthesis of poly functionalized imidazole derivatives by a four component condensation of 1,2-diphenyl 1,2-diketone aromatic aldehydes and ammonium acetate and/or amines in excellent yields. The solvent- and catalyst-free reaction conditions, excellent isolated yields of the products, shorter reaction times, and simple isolation and purification of the products make the present protocol efficient and a green alternative to existing protocols. This journal is
- Patel, Geetika,Patel, Ashok Raj,Banerjee, Subhash
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supporting information
p. 13295 - 13300
(2020/10/07)
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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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- Ferric iron complex containing meta-position carborane ligand as well as preparation method and application of ferric iron complex
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The invention relates to a ferric iron complex containing a meta-carborane triazole ligand as well as a preparation method and application of the ferric iron complex. The ferric iron complex is prepared by the following steps: (1) dropwise adding an n-BuL
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Paragraph 0032; 0039-0041; 0063-0068
(2020/10/14)
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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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- A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones
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We herein report the fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe-Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe-N-C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion.
- Ma, Zhiming,Ren, Peng,Song, Tao,Xiao, Jianliang,Yang, Yong,Yuan, Youzhu
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p. 4617 - 4629
(2020/05/19)
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- Catalytic activity of Mg-Al hydrotalcites and derived mixed oxides for imination reactionsviaan oxidative-dehydrogenation mechanism
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The catalytic activities of Mg-Al hydrotalcites and derived Mg-Al mixed oxides were studied for the imination of benzylic substrates (benzyl amine and benzyl alcohol), with aniline as a model reaction, to establish a green and cost-effective catalytic (precious metal free) process for imination and tandem reactions utilizing alcohols as reagents. The Mg-Al mixed oxide (Mg/Al ratio = 3.0) was found to be an efficient catalyst for imination reactions to synthesize cross-imines with high selectivity as well as for tandem reactions of alcohols. Basic sites of catalysts adsorb benzylic substrates through the hydrogen of their functional groups (-NH2/-OH) and activate (weaken) benzylic C-H bonds for hydride elimination. Thus, basic sites catalyze the reaction by activating benzylic substrates for oxidative-dehydrogenation (i.e., deprotonation followed by hydride elimination with the help of oxygen) to produce reactive imine/carbonyl intermediates, which undergo subsequent nucleophilic reactions with amine.
- Vala, Naresh,Joshi, Pradyuman A.,Mishra, Manish
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supporting information
p. 8859 - 8868
(2020/06/08)
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- Base-promoted annulation of amidoximes with alkynes: Simple access to 2,4-disubstituted imidazoles
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An efficient construction of imidazole ring by a Cs2CO3-promoied annulation of amidoximes with terminal alkynes in DMSO has been developed. This protocol provides a simple synehetic ropte with high atom-utilieation for the synthesis of 2,4-disubstituted imidazoles in good yields under transition-metal-free and ligand-free conditions. Intornal alkynes can also undetgo the annulation to give 2,4,5-trisubstituted imidazoles.
- Hua, Ruimao,Iqbal, Muhammad Asif,Lu, Le,Mehmood, Hina
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- Molecular iodine/DMSO mediated oxidation of internal alkynes and primary alcohols using a one-pot, two step approach towards 2,4,5-trisubstituted imidazoles: Substrate scope and mechanistic studies
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An efficient, eco-friendly and practical oxidation of internal alkynes and primary alcohols as key steps towards the synthesis of 2,4,5-trisubstituted imidazoles is reported. This green synthetic methodology employed an acid and metal-free molecular iodine/DMSO system, to afford a variety of substituted imidazoles in moderate to good yields, with a range of functionalities tolerated. Mechanistic studies revealed two distinct oxidation pathways, which ultimately form the diketone and aldehyde that serve as key intermediates in the multicomponent domino synthesis.
- Jeena, Vineet,Naidoo, Shivani
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supporting information
(2020/02/15)
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- Imidazo-Fused Isoindoles by Pd(II)/Ag(I)-Promoted Intramolecular Dehydrogenative Coupling
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An effective Pd(II)/Ag(I)-promoted intramolecular cross-dehydrogenative coupling (CDC) of substituted 1-benzylimidazoles under air provides, for the first time, a simple access to several functionalized imidazo[2,1-a]isoindoles, an interesting class of polycyclic heteroaromatic compounds. The direct involvement of two unactivated carbon–hydrogen bonds, without any directing group, grants an elevated atom economy of the whole process.
- Lessi, Marco,Lucci, Antonio,Cuzzola, Angela,Bellina, Fabio
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supporting information
p. 796 - 802
(2020/02/20)
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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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- Fe3O4/SO3H@zeolite-Y as a novel multi-functional and magnetic nanocatalyst for clean and soft synthesis of imidazole and perimidine derivatives
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In this study, SO3H@zeolite-Y was synthesized by the reaction of chlorosulfonic acid with zeolite-NaY under solvent-free conditions, which was then supported by Fe3O4 nanoparticles to give SO3H@zeolite-Y (Fe3O4/SO3H@zeolite-Y) magnetic nanoparticles. Several techniques were used to evaluate the physical and chemical characterizations of the zeolitic nanostructures. Fe3O4-loaded sulfonated zeolite was applied as a novel multi-functional zeolite catalyst for the synthesis of imidazole and perimidine derivatives. This efficient methodology has some advantages such as good to excellent yield, high purity of products, reusability of nanocatalyst, simple reaction conditions, environmental friendliness and an economical chemical procedure from the viewpoint of green chemistry.
- Kalhor, Mehdi,Zarnegar, Zohre
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p. 19333 - 19346
(2019/07/05)
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- 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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- 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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- One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc) 2 /Ce(SO 4) 2 /Bi(NO 3) 3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus-Radziszewski Reaction
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A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc) 2 /Ce(SO 4) 2 /Bi(NO 3) 3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus-Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using α-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a β-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72-88percent) under mild conditions.
- Li, Peilang,Li, Yiqun,Sun, Wei,Zhang, Mingjuan
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supporting information
p. 3221 - 3230
(2019/08/28)
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- 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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- Nickel-Catalyzed Hydrophosphonylation and Hydrogenation of Aromatic Nitriles Assisted by Lewis Acid
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In this paper, we describe the catalytic hydrophosphonylation of several aromatic nitriles used to synthesize α-aminophosphonates (α-APs) using commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu,) and simple and inexpensive nickel chloride (NiCl2.6H2O) as the catalytic precursor. The use of triethylborane (Et3B) as a Lewis acid (LA) was mandatory in order to successfully perform H-phosphite moiety incorporation at the CN bond of non-activated benzonitriles (BN) derivatives. Interestingly, when a highly activated BN such as 2,3,4,5,6-pentafluorobenzonitrile (BN-g) was employed, it was possible to perform the reaction in the absence of an LA using milder reaction conditions. Also, we found that using HP(O)(OiPr)2 as a starting material afforded the aminobisphosphonate derivative with better selectivity than using the method involving P(OiPr)3 as the initial reagent. Remarkably, when using HP(O)(OiPr)2 with an excess of Et3B, the reaction's selectivity completely changed to yield N-benzyl- benzylimine (BBI) and 2,4,5-triphenylimidazole.
- Islas, Rosa E.,García, Juventino J.
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p. 1337 - 1345
(2019/02/01)
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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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- One-Pot, Two-Step Metal and Acid-Free Synthesis of Trisubstituted Imidazole Derivatives via Oxidation of Internal Alkynes Using an Iodine/DMSO System
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A one-pot, two-step, simple, efficient and eco-friendly oxidation of internal alkynes as a key step towards the synthesis of 2,4,5-trisubstituted imidazoles, using an inexpensive I2/DMSO system, has been reported. This metal and acid-free synthesis proceeded smoothly to furnish a variety of synthetically useful trisubstituted imidazoles in moderate to excellent yields. In an effort to demonstrate the potential future applications of this system, a double oxidation study was undertaken and the desired trisubstituted imidazoles obtained in good to moderate yields.
- Naidoo, Shivani,Jeena, Vineet
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p. 1107 - 1113
(2019/01/04)
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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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- A 2, 4, 5 - tri-substituted imidazole of preparation method (by machine translation)
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The invention relates to a 2, 4, 5 - tri-substituted imidazole of preparation method, the method is to be sequentially [...] or benzoins, aldehyde compounds, ammonium acetate and catalyst organic acid added in the reactor, in the 85 - 125 °C oil bath under the heating condition the reaction, after the reaction is complete to obtain a reaction mixture; the reaction mixture by washing, filtration, recrystallization after separation, to get the pure product 2, 4, 5 - tri-substituted imidazole. The present invention is simple, the production cost is low, and the yield is high, and has a good industrial application prospect. (by machine translation)
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Paragraph 0014; 0015; 0016; 0017
(2019/04/10)
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- An eco-compatible pathway to the synthesis of mono and bis-multisubstituted imidazoles over novel reusable ionic liquids: An efficient and green sonochemical process
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Novel and environmentally benign ionic liquids (ILs) comprised of DABCO were successfully synthesized. These ILs were used as robust catalysts for the sonochemical one pot multi-component synthetic route for the functionalized annulated imidazoles in water with excellent yields. The present protocol scored well in terms of yield economy as compared with the conventional procedures. The merits of the current green method include simplicity, applicability, broad functional groups tolerance, clean reaction profiles, and no tedious work-up and they give high-to-quantitative yields. From the environmental viewpoint, these eco-friendly green catalysts can be effortlessly retrieved and reused at least seven successive times without substantial loss in catalytic activity.
- Ahmed Arafa, Wael Abdelgayed
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p. 16392 - 16399
(2018/05/22)
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- Cu(II) immobilized on guanidinated epibromohydrin-functionalized γ-Fe2O3@TiO2 (γ-Fe2O3@TiO2-EG-Cu(II)): A highly efficient magnetically separable heterogeneous nanocatalyst for one-pot synthesis of highly substituted imidazoles
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A simple, efficient and eco-friendly procedure has been developed using Cu(II) immobilized on guanidinated epibromohydrin-functionalized γ-Fe2O3@TiO2 (γ-Fe2O3@TiO2-EG-Cu(II)) for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles, via the condensation reactions of various aldehydes with benzil and ammonium acetate or ammonium acetate and amines, under solvent-free conditions. High-resolution transmission electron microscopy analysis of this catalyst clearly affirmed the formation of a γ-Fe2O3 core and a TiO2 shell, with mean sizes of about 10–20 and 5–10?nm, respectively. These data were in very good agreement with X-ray crystallographic measurements (13 and 7?nm). Moreover, magnetization measurements revealed that both γ-Fe2O3@TiO2 and γ-Fe2O3@TiO2-EG-Cu(II) had superparamagnetic behaviour with saturation magnetization of 23.79 and 22.12?emu g?1, respectively. γ-Fe2O3@TiO2-EG-Cu(II) was found to be a green and highly efficient nanocatalyst, which could be easily handled, recovered and reused several times without significant loss of its activity. The scope of the presented methodology is quite broad; a variety of aldehydes as well as amines have been shown to be viable substrates. A mechanism for the cyclocondensation reaction has also been proposed.
- Nejatianfar, Mahdi,Akhlaghinia, Batool,Jahanshahi, Roya
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- 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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- 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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- Co(II) anchored glutaraldehyde crosslinked magnetic chitosan nanoparticles (MCS) for synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles
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A simple, highly efficient and green synthesis of 2,4,5-trisubsituted and 1,2,4,5-tetrasubstituted imidazoles was developed using a novel MCS-GT@Co(II) magnetically recoverable and recyclable catalyst under refluxing conditions with ethanol as a solvent. The catalyst was prepared by immobilization of chitosan onto Fe3O4 using glutaraldehyde as crosslinker followed by Co(II) ion immobilization via cobalt acetate. The catalyst was characterized using various techniques. For organic products determination, 1H NMR, 13C NMR and Fourier transform infrared spectroscopies were used. The reaction was also tried with individual components of the catalyst, but the synergistic effect of the components in the prepared catalyst showed the highest yield and shortest reaction time.
- Singh, Harminder,Rajput, Jaspreet Kaur
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- 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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- Magnetically separable and recyclable g-C3N4 nanocomposite catalyzed one-pot synthesis of substituted imidazoles
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A green, reliable synthetic method and highly efficient one-pot three-component synthesis of 2,4,5-trisubstituted imidazoles from 1,2-diketones, aldehydes and ammonium acetate in the presence of recyclable magnetic graphitic carbon nitride nanocomposite (Fe3O4@g-C3N4) has been developed. Various imidazole derivatives were obtained in moderate to excellent yields and high purity after recrystallization from ethanol. Interestingly, the low-cost Fe3O4@g-C3N4 a nontoxic and inexpensive catalyst showed excellent recyclability using an external magnet without loss of parent catalytic activity even after ten cycles and its provides new opportunities for the truly environmental friendliness methodology.
- Ahooie, Tahereh Soleymani,Azizi, Najmedin,Yavari, Issa,Hashemi, Mohammad Mahmoudi
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p. 855 - 862
(2018/03/01)
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- 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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- ZnCl2-Catalyzed [3 + 2] Cycloaddition of Benzimidates and 2 H-Azirines for the Synthesis of Imidazoles
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ZnCl2-catalyzed [3 + 2] cycloaddition reaction of benzimidates and 2H-azirines has been developed. This convenient method allowed the efficient construction of a series of multisubstituted imidazoles in moderate to good yields under mild reaction conditions. This transformation exhibits good reactivity and high functional group tolerance.
- Shi, Shoujie,Xu, Kang,Jiang, Cheng,Ding, Zhenhua
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p. 14791 - 14796
(2018/11/23)
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