5496-37-7Relevant academic research and scientific papers
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
Aberi, Mahdi,Razavi, Seyyede Faeze,Sharghi, Hashem
, (2021/08/16)
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.]
Urea-Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel
Higuera, Natalia López,Pe?a-Solórzano, Diana,Ochoa-Puentes, Cristian
supporting information, p. 225 - 229 (2019/01/14)
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.
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
Nejatianfar, Mahdi,Akhlaghinia, Batool,Jahanshahi, Roya
, (2017/10/23)
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.
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
Kolvari, Eskandar,Zolfagharinia, Somayeh
, p. 93963 - 93974 (2016/10/21)
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.
Ionophore silica-coated magnetite nanoparticles as a recyclable heterogeneous catalyst for one-pot green synthesis of 2,4,5-trisubstituted imidazoles
Naeimi, Hossein,Aghaseyedkarimi, Dorsa
, p. 1243 - 1253 (2016/01/15)
Novel multi-SO3H functionalized strong Br?nsted acidic ionic liquid coated magnetite nanoparticles have been prepared and applied as catalyst for the synthesis of 2,4,5-trisubstituted imidazoles. The results showed that a novel catalyst was very efficient for the reaction and could be magnetically separated and reused at least 6 times with less reduction in its catalytic activity. Operational simplicity, low cost of the catalyst used, high yields, environmental friendliness, wide applicability, reusability and easy recovery of the catalyst using an external magnet are the most important features of this methodology. The catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), X-Ray diffraction analysis (XRD), field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray analysis (EDX), dynamic laser scattering (DLS) and vibrating sample magnetometry (VSM).
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
Mirsafaei, Razieh,Heravi, Majid M.,Ahmadi, Shervin,Hosseinnejad, Tayebeh
, p. 418 - 429 (2016/03/08)
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.
Perlite: An inexpensive natural support for heterogenization of HBF4
Kolvari, Eskandar,Koukabi, Nadiya,Hosseini, Maliheh M.,Khandani, Zeinab
, p. 36828 - 36836 (2015/05/05)
Nano-perlite-fluoroboric acid (n-PeFBA) has been synthesized by immobilization of HBF4 on perlite to produce an efficient green heterogeneous reusable solid acid catalyst. The catalyst was characterized by (FE-SEM, EDX, BET and BJH). This catalyst was employed to prepare biologically important 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles with high yields and selectivities. Advantages of solid acid include: low cost, facile handling, simple preparation, high stability, reusability and low toxicity. The catalyst could be recovered and reused for several runs without deterioration in catalytic activity.
Fe3O4@SiO2·HM·SO3H as a recyclable heterogeneous nanocatalyst for the microwave-promoted synthesis of 2,4,5-trisubstituted imidazoles under solvent free conditions
Naeimi, Hossein,Aghaseyedkarimi, Dorsa
, p. 9415 - 9421 (2015/12/01)
A simple, highly versatile and efficient synthesis of 2,4,5-trisubstituted imidazoles is achieved through a three component one pot reaction of benzil, benzaldehyde and NH4OAc. This reaction has been catalyzed by Fe3O4@SiO2·HM·SO3H, a very efficient, novel recyclable heterogeneous catalyst, under microwave irradiation and solvent free conditions. The catalyst can be recovered for the subsequent reactions and reused for at least five rounds, without any appreciable loss of its efficiency.
Shape-dependent catalytic activity of Fe3O4 nanostructures under the influence of an external magnetic field for multicomponent reactions in aqueous media
Rafiee,Joshaghani,Ghaderi-Shekhi Abadi
, p. 74091 - 74101 (2015/09/15)
High-quality and high-active one-dimensional (1-D) Fe3O4 nanostructures were synthesized via an external magnetic field (EMF) at the intensity range 0-526 μT in aqueous solution, without using any surfactant and organic solvent at room temperature. Characterization of the products was carried out using scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), X-ray diffraction spectroscopy (XRD), Fourier transform infrared spectrophotometry (FT-IR), a laser particle size analyzer, surface area (Brunauer-Emmett-Teller, BET), and vibrating sample magnetometer (VSM). The results show that EMF at a critical adjusted intensity has a great influence on the structural features such as the morphology, particle size, surface pore size distribution, and magnetic properties of the Fe3O4 nanostructure. The morphology changed from peg-like network structures to needle-like cage structures by an exposure synthesis treatment with EMF at an intensity of 362 μT. The catalytic activity of two nanostructures prepared in the presence and absence of EMF were compared in a tricomponents reaction (TCR) for the synthesis of trisubstituted imidazoles under electromagnetic irradiation. The best results were obtained for the catalyst produced in the presence of EMF while the tricomponent reaction was carried out in the absence of EMF. This EMF condition was used for the preparation of a series of alkyl-, aryl-, and heteroaryl-substituted imidazoles from the corresponding benzoin and benzil in aqueous solution as green reaction conditions. It was found that the catalyst can be efficiently recycled and reused for several repeating cycles without significant loss of catalytic activity.
Deep eutectic solvent for multi-component reactions: A highly efficient and reusable acidic catalyst for synthesis of 2,4,5-triaryl-1H-imidazoles
Bakavoli, Mehdi,Eshghi, Hossein,Rahimizadeh, Mohammad,Housaindokht, Mohammad Reza,Mohammadi, Ali,Monhemi, Hassan
, p. 3497 - 3505 (2015/06/08)
Efficient synthesis of 2,4,5-trisubstituted imidazoles has been achieved by three-component cyclocondensation of benzil or benzoin, an aldehyde, and ammonium acetate by use of an acidic catalyst. The catalyst is a deep eutectic mixture of choline chloride and oxalic acid that is non-toxic and biodegradable. Crucial advantages of this process are high yields, shorter reaction times, easy work-up, purification of products by non-chromatographic methods, and reusability of the catalyst.
