- 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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- 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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- Homoselective synthesis of 5-substituted 1H-tetrazoles and one-pot synthesis of 2,4,5-trisubstuted imidazole compounds using BNPs@SiO2-TPPTSA as a stable and new reusable nanocatalyst
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Considering the importance of tetrazole and imidazole derivatives in pharmacy, industry, and explosives, BNPs@SiO2-TPPTSA was easily prepared and used as an effective, stable, and renewable nanocatalyst for the homoselective synthesis of different 5-substituted 1H-tetrazoles and atom economic synthesis of 2,4,5-trisubstituted-1H-imidazoles in solventless conditions. BNPs@SiO2-TPPTSA was characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD), energy dispersive X-ray analysis (EDX), thermal gravimetric-differential thermal analysis (TGA-DTA), mapping, pH analysis, and Fourier transform infrared (FT-IR) techniques. Furthermore, the catalyst recycled for at least sequential five loads without a remarkable drop-in catalytic activity.
- Khodamorady, Minoo,Ghobadi, Nazanin,Bahrami, Kiumars
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- Magnetic 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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- 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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- 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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- 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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p. 2245 - 2261
(2021/03/31)
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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 fabrication of porous magnetic covalent organic frameworks as robust platform for multicomponent reaction
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The design of cheap yet efficient nanoporous magnetic catalysts for the environmentally benign process's widespread application is an extremely attractive, challenging chemical research field. A novel porous magnetic covalent organic framework was prepared by the condensation reaction of melamine and terephthaladehyde on the surface of 3,4-dihydroxybenzaldehyde coated magnetic Fe3O4 nanoparticles COF@Fe3O4 under hydrothermal conditions for the first time. The high surface area magnetic COF could exhibit superior catalytic activity for sustainable synthesis of trisubstituted and tetrasubstituted imidazoles and pyrroles in good to excellent yields in PEG as solvent under environmentally friendly, ambient conditions and making the overall process economical, efficient, and green. The retrievable catalyst in PEG is general and applicable to a broad substrate scope and functional group compatibility. The structure and morphology of the COF@Fe3O4 were characterized by FTIR, XRD, EDX, and SEM spectroscopy. The COF@Fe3O4 magnetic catalyst was recovered by an external magnet and used for several cycles without significant catalytic activity loss.
- Azizi, Najmedin,Heidarzadeh, Fatemeh,Farzaneh, Fezeh
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- Synthesis and characterization of a new polymeric catalyst and used for the synthesis of imidazole derivatives
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Cross-linked poly (4-vinylpyridine) supported TiCl4 abbreviated as [P4-VP]-Ti(IV) as a new polymeric catalyst was easily prepared and characterized by using the X-ray spectroscopy, EDS, mapping, TGA/DTG and FTIR techniques. This catalyst was used for synthesis of imidazole derivatives via one-pot three-component condensation reaction of benzil, ammonium acetate and aldehydes. This protocol offers advantages such as short reaction time, simple reaction work-up with reusability of catalyst. Graphic abstract: [Figure not available: see fulltext.].
- Karimi Zarchi, Mohammad Ali,Behboodi, Kazem,Mirjalili, Bibi Fatemeh
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p. 4929 - 4942
(2021/09/06)
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- Bronsted acidic ionic liquid catalyzed an eco-friendly and efficient procedure for synthesis of 2,4,5-trisubstituted imidazole derivatives under ultrasound irradiation and optimal conditions
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Abstract: 2-[(1H-imidazol-3-ium-3-yl)methyl]-4-{bis[3-((1H-imidazol-3-ium-3-yl) methyl-(4-hydroxyphenyl]methylene}cyclohexa-2,5-dienone trihydrogen sulfate ([2-(imm)-4-{b(immh)m}c][HSO4]3), as the new Bronsted acidic ionic liquid, is effectively prepared and revealed by using FTIR, 1H NMR, SEM, EDS, XRD and mass data. Afterward, its catalytic activity was investigated for the synthesis of 2,4,5-trisubstituted imidazole derivatives via the simple reaction between different aldehydes, ammonium acetate and benzil/benzoin under ultrasound irradiation at ambient temperature and optimal conditions. The novel procedure has the advantages of high yields, easy handling, short reaction times, and being eco-friendly and economical. Moreover, the catalyst can be easily recovered for several times without any additional treatment. Graphic abstract: [Figure not available: see fulltext.].
- Hilal,Hanoon
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p. 1521 - 1538
(2019/12/02)
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- 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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- 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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- 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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- 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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- 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
- -
-
Paragraph 0032; 0039-0041; 0042
(2020/10/14)
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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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- 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)
- -
-
Paragraph 0030; 0031; 0032
(2019/04/10)
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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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- Sulfonated-polyvinyl amine coated on Fe3O4 nanoparticles: a high-loaded and magnetically separable acid catalyst for multicomponent reactions
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Abstract: In this study, a PVAm-bearing SO3H groups/Fe3O4 nanocomposite was prepared via a simple and in situ polymerization of acrylamide onto the surface of magnetic nanoparticles without using organosilane precursors. In order to obtain amine-functionalized magnetic, Hofmann degradation was carried out. In the following, sulfonated-polyvinyl amine coated on Fe3O4 nanoparticles was prepared by covalent grafting of chlorosulfonic acid on amine groups. The introduction of polymer to the surface of magnetic nanoparticles increases the loading content with functional groups extremely. The resulting hybrid material was effectively employed as an unprecedented acid magnetic catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions. High yields, mild reaction conditions, short reaction times, operational simplicity with reusability are the notable features of the catalyst. The structure of the newly developed catalyst was characterized using TGA, FT-IR, SEM, TEM, VSM, EDX, CHNS, and XRD analysis. Magnetic separation and recycling of the catalyst for at least 8 runs is possible without any significant deterioration in catalytic activity. This work is the first report of employing PVAm as a linker for immobilizing liquid acid on a support.
- Arghan, Maryam,Koukabi, Nadiya,Kolvari, Eskandar
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p. 2333 - 2350
(2019/06/17)
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- An efficient multicomponent synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetic nanoparticle supported Lewis acidic deep eutectic solvent
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A mild and highly efficient reaction for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetically supported Lewis acidic deep eutectic solvent on magnetic nanoparticles (LADES?MNP) has been developed via one-pot multicomponent processes under solvent-free sonication. These reactions have good to excellent yields, mild conditions, and work-up simplicity. This method represents a new method for the preparation of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles. More importantly, LADES?MNP can be easily recovered by magnetic separation and reused five times without significant loss of catalytic activity.
- Nguyen, Thanh Thi,Thi Le, Ngoc-Phuong,Nguyen, The Thai,Tran, Phuong Hoang
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p. 38148 - 38153
(2019/12/03)
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- 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 and characterization of amino glucose-functionalized silica-coated NiFe2O4 nanoparticles: A heterogeneous, new and magnetically separable catalyst for the solvent-free synthesis of 2,4,5–trisubstituted imidazoles, benzo[d]imidazoles, benzo[d] oxazoles and azo-linked benzo[d]oxazoles
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Amino glucose-functionalized silica-coated NiFe2O4 nanoparticles (NiFe2O4@SiO2@amino glucose) were chemically synthesized and characterized by transmission electron microscope (TEM), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), energy dispersive X-ray analysis (EDX), vibrating sample magnetometer (VSM), Zetasizer and Fourier transform infrared spectroscopy (FT-IR) instruments. NiFe2O4@SiO2@amino glucose supply an environmentally friendly procedure for the synthesis of 2,4,5-trisubstituted imidazoles through one-pot multicomponent condensation of benzil or benzoin, ammonium acetate with aryl aldehydes and for the synthesis of benzoxazoles using condensation reaction of 2-aminophenol with aryl aldehydes under solvent free condition. In the other study, this synthesized magnetically reusable catalyst was introduced as a new avenue for the synthesis of benzo[d]imidazoles using the reaction between aryl aldehydes and 1,2-diaminobenzene. These compounds were obtained in high yields and short reaction times. The catalyst could be easily recovered and reused for five cycles with almost consistent activity. Synthesized compounds were characterized by their physical constant, comparison with authentic samples, FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.
- Fekri, Leila Zare,Nikpassand, Mohammad,Shariati, Shahab,Aghazadeh, Behnaz,Zarkeshvari, Reza,Norouz pour, Nahid
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- An eco-compatible pathway to the synthesis of mono and bis-multisubstituted imidazoles over novel reusable ionic liquids: An efficient and green sonochemical process
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Novel and environmentally benign ionic liquids (ILs) comprised of DABCO were successfully synthesized. These ILs were used as robust catalysts for the sonochemical one pot multi-component synthetic route for the functionalized annulated imidazoles in water with excellent yields. The present protocol scored well in terms of yield economy as compared with the conventional procedures. The merits of the current green method include simplicity, applicability, broad functional groups tolerance, clean reaction profiles, and no tedious work-up and they give high-to-quantitative yields. From the environmental viewpoint, these eco-friendly green catalysts can be effortlessly retrieved and reused at least seven successive times without substantial loss in catalytic activity.
- Ahmed Arafa, Wael Abdelgayed
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p. 16392 - 16399
(2018/05/22)
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- 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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- Green Synthesis of 1,2,4,5-Tetrasubstituted and 2,4,5-Trisubstituted Imidazole Derivatives Involving One-pot Multicomponent Reaction
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Sodium lauryl sulfate has been found convenient, versatile, and eco-friendly catalyst for the synthesis of 1,2,4,5-tetrasubstituted and 2,4,5-trisubstituted imidazole derivatives by one-pot multicomponent reactions at 80°C using water as solvent. This protocol afforded advantages, that is, the metal-free reaction, purification of products by non-chromatographic method, and excellent yields.
- Bansal, Ravi,Soni, Pradeep K.,Halve, Anand K
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p. 1308 - 1312
(2018/04/25)
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- 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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- 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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- 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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- 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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- Appel reagent as novel promoter for the synthesis of polysubstituted imidazoles
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We present an efficient method for the synthesis of polysubstituted imidazoles in the presence of Appel reagent (Ph3P/CCl4). Tri-substituted imidazoles is synthesized via condensation of aldehydes, benzil and ammonium acetate, and tetra-substituted imidazole is prepared via condensation of aldehydes, benzil, ammonium acetate and primary amines. These protocols allow the simple preparation of the desired products using readily available reagent instead of complex, expensive and toxic reagents under mild reaction conditions in excellent yields.
- Khoshneviszadeh, Mehdi,Mahdavi, Mohammad
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p. 343 - 352
(2018/05/07)
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- One-pot synthesis of multisubstituted imidazoles catalyzed by Dendrimer-PWAn nanoparticles under solvent-free conditions and ultrasonic irradiation
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An efficient, green and eco-friendly protocol has been developed for the synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles via one-pot condensation reaction using Dendrimer-PWAn as catalyst under solvent-free conditions or ultrasonic irradiation in excellent yields. The reactions under conventional heating conditions were compared with the ultrasonic-assisted reactions. The operational simplicity, practicability and applicability of this protocol to various substrates make it an interesting alternative to previous procedures. The present methodology offers several advantages such as excellent yields, short reaction times, a cleaner reaction, and the absence of any tedious work-up or purification. The catalyst is easily separated from the products by filtration and also exhibits remarkable reusable activity. SEM, BET and DLS of the catalyst were also investigated after each reaction cycle.
- Esmaeilpour, Mohsen,Javidi, Jaber,Dehghani, Farzaneh,Zahmatkesh, Saeed
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p. 163 - 185
(2017/01/14)
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- Crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes: A bio-nanoreactor with extremely high activity toward click-multi-component reactions
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In the present study, we have designed a procedure for the synthesis of a bio-nanoreactor catalyst, crosslinked chitosan nanoparticle-anchored magnetic multi-wall carbon nanotubes (CS NPs/MWCNT@Fe3O4), via an in situ ionotropic gelation method. The synthesized robust nanoreactor was fully characterized. Moreover, the catalytic activity was investigated towards the click-based multi-component reactions for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, trisubstituted imidazoles, and 1,2,3-triazoles in a green medium. Since the nanocatalyst can be recovered by applying an external magnetic field, which results in easy separation without filtration, and recycled several times without the loss of its significant activities, it shows admirable potential in reusable catalysis.
- Shaabani, Ahmad,Afshari, Ronak,Hooshmand, Seyyed Emad
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p. 8469 - 8481
(2017/08/14)
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- Identification and Mechanistic Evaluation of Hemozoin-Inhibiting Triarylimidazoles Active against Plasmodium falciparum
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In a previous study, target based screening was carried out for inhibitors of β-hematin (synthetic hemozoin) formation, and a series of triarylimidazoles were identified as active against Plasmodium falciparum. Here, we report the subsequent synthesis and testing of derivatives with varying substituents on the three phenyl rings for this series. The results indicated that a 2-hydroxy-1,3-dimethoxy substitution pattern on ring A is required for submicromolar parasite activity. In addition, cell-fractionation studies revealed uncommonly large, dose-dependent increases of P. falciparum intracellular exchangeable (free) heme, correlating with decreased parasite survival for β-hematin inhibiting derivatives.
- Wicht, Kathryn J.,Combrinck, Jill M.,Smith, Peter J.,Hunter, Roger,Egan, Timothy J.
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supporting information
p. 201 - 205
(2017/03/08)
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- Highly efficient and simple protocol for synthesis of 2,4,5-triarylimidazole derivatives from benzil using fluorinated graphene oxide as effective and reusable catalyst
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Abstract: Efficient synthesis of 2,4,5-triarylimidazole derivatives with simple workup is described using benzil, different aldehydes, and ammonium acetate in presence of fluorinated graphene oxide (A-MFGO) as effective catalyst that can be easily recover
- Hanoon,Kowsari,Abdouss,Ghasemi,Zandi
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p. 4023 - 4041
(2017/06/20)
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- Caffeine-H3PO4: a novel acidic catalyst for various one-pot multicomponent reactions
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Caffeine-H3PO4 along with caffeine-HClO4 and caffeine-HNO3 have been prepared and applied for one-pot preparation of bis(indolyl) methanes, 4,4′-(arylmethylene) bis(1H-pyrazol-5-ols), 3,3′-(arylmethylene) bis(4-hydroxycoumarins), 2,4,5-trisubstituted imidazoles, 1‐amidoalkyl‐2‐naphthols, and polyhydroquinolines. The catalysts were characterized using Fourier-transform infrared (FTIR) spectroscopy, 1H and 13C nuclear magnetic resonance (NMR), powder X-ray diffraction (PXRD) analysis, thermogravimetric analysis (TGA), and liquid chromatography (LC)–mass spectroscopy (MS) techniques. The results indicated high product yield, short reaction time, facile separation of catalyst, and easy work-up procedure, suggesting that caffeine-H3PO4 can be considered to be an efficient acidic catalyst for organic transformations.
- Saghanezhad, Seyyed Jafar,Sayahi, Mohammad Hosein,Imanifar, Iman,Mombeni, Mostafa,Deris Hamood, Sajedeh
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p. 6521 - 6536
(2017/10/06)
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- Synthesis and characterization of nano-copper ferrite as a magnetically separable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free condition
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The authors report herein, synthesis and characterization of nano-copper ferrite as a recoverable, ecofriendly, inexpensive, and readily available catalyst for efficient, simple, and green synthesis of multisubstituted imidazoles. Short reaction times, high yields, easy workup, and mild condition are the advantages of this protocol. The catalyst can be reused without evident loss of the catalytic activity. Characterization of the catalyst was performed fully by Fourier transform infrared spectra, X-ray diffraction, FESEM, electron dispersive X-ray, and vibration sampling magnetometer analyses.
- Nemati, Firouzeh,Elhampour, Ali,Bagheri Natanzi, Mahshid
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p. 666 - 671
(2017/08/10)
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- An Efficient and Green Synthesis of Imidazoles Using Natural Organic Acids as Promoter under Solvent-Free Condition
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An efficient and eco-friendly synthesis of imidazoles, promoted by naturally occurring acids, via condensation of benzil, aldehyde and ammonium acetate using conventional and microwave heating under solvent-free condition is described. Reactions under mic
- Dhawale, Kiran D.,Thorat, Nitin M.,Patil, Limbraj R.
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p. 1702 - 1712
(2017/06/27)
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- 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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p. 474 - 480
(2017/05/19)
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- Isocyanurate-based periodic mesoporous organosilica (PMO-ICS): A highly efficient and recoverable nanocatalyst for the one-pot synthesis of substituted imidazoles and benzimidazoles
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Isocyanurate bridging periodic mesoporous organosilica (PMO-ICS) was shown to be a highly active and efficient recyclable catalyst for the three-component synthesis of imidazole derivatives from benzoin, different aldehydes and ammonium acetate under mild reaction conditions in short reaction times and good to excellent yields in EtOH. Also, benzimidazole derivatives were efficiently prepared from o-phenylenediamine and different aldehydes in the presence of PMO-ICS. Moreover, the catalyst was also recovered and reused at least four times without a significant decrease in its activity. The PMO-ICS catalyst was characterized by Fourier transformer infrared (FTIR) spectroscopy, thermogravimetry analysis (TGA), powder X-ray diffraction (XRD) and nitrogen adsorption-desorption isotherm (NADI) techniques as well as field emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM). Compared to the classical methodologies, this method illustrated significant advantages including low loading of the catalyst, avoiding the use of toxic transition metals or reactive reagents for modification of the catalytic activity, short reaction times, high to excellent yields, easy separation and purification of the products, and reusability of the catalyst.
- Dekamin, Mohammad G.,Arefi, Elham,Yaghoubi, Amene
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p. 86982 - 86988
(2016/10/19)
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- 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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- Design, preparation and characterization of Cu/GA/Fe3O4@SiO2 nanoparticles as a catalyst for the synthesis of benzodiazepines and imidazoles
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The synthesis and characterization of an efficient and reusable nanocatalyst, Cu/GA/Fe3O4@SiO2, obtained by ultrasonic-assisted grafting of guanidineacetic acid on modified Fe3O4@SiO2 core-shell nanocomposite spheres and subsequent immobilization of Cu(II), are described. The catalyst was characterized by means of X-ray diffraction, scanning and transmission electron microscopies, energy-dispersive X-ray spectroscopy, elemental analysis, thermogravimetric analysis, Fourier transform infrared spectroscopy, vibrating sample magnetometry and inductively coupled plasma optical emission spectrometry. The prepared nanocatalyst facilitated an efficient and straightforward friendly procedure for the synthesis of benzodiazepines and imidazoles in ethanol and under solvent-free conditions, respectively. The nanocatalyst can be easily recovered using a magnet and reused several times without any significant loss of activity.
- Shaabani, Ahmad,Sepahvand, Heshmatollah,Hooshmand, Seyyed Emad,Borjian Boroujeni, Mahmoud
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p. 414 - 421
(2016/05/19)
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- Synthesis and properties of novel reusable nano-ordered KIT-5-N-sulfamic acid as a heterogeneous catalyst for solvent-free synthesis of 2,4,5-triaryl-1H-imidazoles
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A novel silica-bonded propyl-N-sulfamic acid nanocatalyst (NHSO3H-KIT-5) supported on modified silica mesopore KIT-5 as an organic-inorganic hybrid with high specific surface area was successfully prepared. The 3-aminopropyltriethoxysilane (APTES) on KIT-5 was reacted with chlorosulfonic acid and accurately characterized by the FT-IR, XRD, SEM, EDAXS, and TGA techniques. This heterogeneous and recyclable catalyst catalyzed one pot, multicomponent condensation of benzil, aromatic aldehydes, and ammonium acetate in the presences of 0.05 g of nanocatalyst under solvent-free conditions to afford triaryl-imidazoles in excellent yields. This catalyst showed high catalytic activity under green conditions. This reaction was performed under open air conditions and required no special reaction conditions or chromatographic separation for purification.
- Mirsafaei, Razieh,Heravi, Majid M.,Ahmadi, Shervin,Hosseinnejad, Tayebeh
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p. 418 - 429
(2016/03/08)
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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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