- Effect of OH, NH2 and OCH3 groups on the corrosion inhibition efficacy of three new 2,4,5-trisubstituted imidazole derivatives on mild steel in acidic solutions: Experimental, surface and DFT explorations
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Three new imidazole derivatives namely,4-(4,5-bis(4-methoxyphenyl)-1H-imidazol-2-yl)phenol (IM1), 4-(4,5-bis(4-methoxyphenyl)-1H-imidazol-2-yl)benzenamine (IM2), 2,4,5-tris(4-methoxy phenyl)-1H-imidazole (IM3) were synthesized using microwave irradiation method. The noteworthy highlights of this method are safe reaction profiles, broad substrate scope, short run time, catalyst-free, excellent yields, economical, solvent-free, and simple workup conditions. The structural characterization of all the imidazole derivatives has been confirmed by 1HNMR and mass spectral techniques. The corrosion inhibition potential of all the imidazoles was explored using weight loss and electrochemical methods. The imidazole derivative (IM1) bearing a hydroxyl group exhibited maximum corrosion inhibition efficiency compared to other imidazoles (up to 96%). Strong adsorption of studied imidazole molecules followed the Langmuir model with very good correlation coefficients. The calculated Gibbs free energy of adsorption values suggested the mixed type of adsorption (physisorption and chemisorption). The polarization measurements indicated studied imidazole derivatives as mixed types of corrosion inhibitors. Further, scanning electron microscopy (SEM), XPS and XRD were performed to study the surface morphology of Mild steel (MS) surface. Quantum chemical calculations (DFT) was used to prove the obtained inhibition efficiencies (η %).
- Prashanth,Kumar, C.B. Pradeep,Prathibha,Raghu,Kumar, K. Yogesh,Jagadeesha,Mohana,Krishna, Honnur
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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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- Preparation method for 2,4,5-trisubstituted imidazole compound
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The invention relates to a preparation method for 2,4,5-trisubstituted imidazole. According to the method, benzylamine is used as a substrate, and ZnIn2S4 is used as a photocatalyst; and under the condition of illumination of visible light, benzylamine un
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Paragraph 0021; 0022; 0023; 0024; 0025
(2019/03/26)
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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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- Photocatalytic coupling of amines to imidazoles using a Mo-ZnIn2S4 catalyst
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Substituted imidazoles are traditionally synthesized by co-condensation of multiple feedstocks. Herein, we report a new route for the synthesis of substituted imidazoles via photocyclization of readily available amines at room temperature. The reaction is achieved by the visible-light-induced C-C/C-N bond coupling and subsequent dehydrogenation reaction over Mo-ZnIn2S4 as a heterogeneous photocatalyst. A wide range of amines were converted into the corresponding tri- and tetra-substituted imidazoles with up to 96% total yields. The simplicity, high efficiency and mild condition merits of this new reaction will enable it to be useful in synthetic transformations.
- Wang, Min,Li, Lihua,Lu, Jianmin,Luo, Nengchao,Zhang, Xiaochen,Wang, Feng
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p. 5172 - 5177
(2017/11/09)
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- Fused imidazoles as potential chemical scaffolds for inhibition of heat shock protein 70 and induction of apoptosis. Synthesis and biological evaluation of phenanthro[9,10-d] imidazoles and imidazo[4,5-f] [1,10]phenanthrolines
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The imidazole ring is widespread in biologically active compounds, and hence imidazole-containing scaffolds are useful starting points for drug discovery programmes. We report the synthesis of a series of novel imidazole-containing compounds fused with either phenanthrene or phenanthroline, which show enhanced growth inhibitory potency against human colon, breast and melanoma cancer cell lines, as well as evidence of inhibition of the molecular chaperone heat shock protein 70 (Hsp70) pathway in cells, as shown by depletion of downstream oncogenic client proteins of the Hsp90 chaperone pathway, and induction of apoptosis.
- Patel, Alpa,Sharp, Swee Y.,Hall, Katelan,Lewis, William,Stevens, Malcolm F.G.,Workman, Paul,Moody, Christopher J.
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p. 3889 - 3905
(2016/05/19)
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- Efficient synthesis of 2,4,5-triaryl-1H-imidazoles from aromatic aldehydes with HMDS catalyzed by N-bromosaccharin (NBSa)
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A one-pot efficient procedure for the synthesis of 2, 4, 5-triaryl-1H-imidazole derivatives by the reactions of hexamethyldisilazane and arylaldehydes in the presence of N-bromosaccharin (NBSa) is studied. This new method offers several advantages, such as excellent yields, easy workup, short reaction times, and simple procedure.
- Sedrpoushan, Alireza,Joshani, Zinab,Fatollahi, Leila
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p. 287 - 292
(2014/05/20)
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- Fe3O4@chitosan nanoparticles: A valuable heterogeneous nanocatalyst for the synthesis of 2,4,5-trisubstituted imidazoles
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Chitosan-coated Fe3O4 nanoparticles (Fe 3O4@CS) were prepared simply through in situ co-precipitation of Fe2+ and Fe3+ ions via NH 4OH in an aqueous solution of chitosan and their catalytic activity was investigated in the synthesis of 2,4,5-trisubstituted imidazoles by a one-pot condensation of benzil derivatives, aryl aldehydes and ammonium acetate in EtOH. This novel method offers several advantages compared to those reported in the previous literature, including avoiding the use of harmful catalysts, easy and quick isolation of the products, excellent yields, mild and clean conditions, and simplicity of the methodology. High catalytic activity and ease of recovery using an external magnetic field are additional eco-friendly attributes of this catalytic system. This journal is the Partner Organisations 2014.
- Zarnegar, Zohre,Safari, Javad
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p. 20932 - 20939
(2014/06/09)
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- A highly efficient magnetic solid acid catalyst for synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation
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Fe3O4 nanoparticles were prepared by chemical coprecipitation method and subsequently coated with 3-aminopropyltriethoxysilane (APTES) via silanization reaction. Grafting of chlorosulfuric acid on the amino-functionalized Fe3O4 nanoparticles afforded sulfamic acid-functionalized magnetic nanoparticles (SA-MNPs). SA-MNPs was found to be a mild and effective solid acid catalyst for the efficient, one-pot, three-component synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation. This protocol afforded corresponding imidazoles in shorter reaction durations, and in high yields. This green procedure has many obvious advantages compared to those reported in the previous literatures, including avoiding the use of harmful catalysts, easy and quick isolation of the products, excellent yields, short routine, and simplicity of the methodology.
- Safari, Javad,Zarnegar, Zohre
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p. 740 - 746
(2013/02/22)
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- One-pot synthesis of polysubstituted imidazoles from arylaldehydes in water catalyzed by nhc using microwave irradiation
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A simple, high yielding synthesis of tri (3a-i) and tetrasubstituted (4a-g) imidazols from aldehydes is described. The cornerstone of this methodology involves the condensation of NH4OAc, substituted aldehydes, and benzoin, which is synthesized in situ from aldehydes catalyzed by N-heterocyclic carbine (NHC), under microwave irradiation in water to afford trisubstituted imidazoles (3a-i). If arylamine is added in the solution, tetrasubstituted imidazoles (4a-g) can be obtained. Lepidilines B and trifenagrel are also synthesized in high yield using this procedure. All the experiment deta are in agreement with the literature.
- Wu, Lei,Jing, Xiaobi,Zhu, Hongxiang,Liu, Yinlin,Yan, Chaoguo
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p. 1204 - 1207
(2013/03/28)
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- Convenient one-pot synthesis of 2,4,5-triaryl-1H-imidazoles from arylaldehydes, benzyl alcohols, or benzyl halides with HMDS in the presence of molecular iodine
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A one-pot efficient procedure for the synthesis of 2,4,5-triaryl-1 H-imidazole derivatives in good to excellent yields by reaction between hexamethyldisilazane and arylaldehydes, benzyl alcohols, benzyl halides in the presence of molecular iodine has been developed. The remarkable advantages of this method are the simple workup procedure, high yields of products, and the availability of reagents.
- Veisi, Hojat,Khazaei, Ardashir,Heshmati, Leila,Hemmati, Saba
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experimental part
p. 1231 - 1234
(2012/07/14)
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- Zinc (II) [tetra(4-methylphenyl)] porphyrin: A novel and reusable catalyst for efficient synthesis of 2,4,5-trisubstituted imidazoles under ultrasound irradiation
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An efficient three-component one-step synthesis of 2,4,5-trisubstituted imidazoles by condensation reaction of 1,2-diketones or a-hydroxyketones with aromatic aldehydes and ammonium acetate using Zinc (II) [tetra (4-methylphenyl)] porphyrin as a novel and reusable catalyst under ultrasound irradiation at ambient temperature is described. In this method, a-hydroxyketones as well as 1,2-diketones were converted to their corresponding 2,4,5-trisubstituted imidazoles in excellent yields. Copyright
- Safari, Javad,Khalili, Shiva Dehghan,Banitaba, Sayed Hossein,Dehghani, Hossein
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experimental part
p. 787 - 793
(2012/01/05)
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- One-pot synthesis of imidazoles from aromatic nitriles with nickel catalysts
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Nickel(0) catalysts were used to produce substituted imidazoles in good to high yields using benzonitrile, p-substituted benzonitriles and 4-cyanopyridine as starting materials. The Royal Society of Chemistry 2011.
- Garcia, Juventino J.,Zerecero-Silva, Paulina,Reyes-Rios, Grisell,Crestani, Marco G.,Arevalo, Alma,Barrios-Francisco, Rigoberto
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supporting information; experimental part
p. 10121 - 10123
(2011/10/09)
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- One-pot synthesis of 2,4,5-triaryl-1 H -imidazoles from arylaldehydes, benzyl alcohols, or benzyl halides with hexamethyldisilazane in molten tetrabutylammonium bromide
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A simple and efficient method for the synthesis of 2,4,5-triaryl-1H- imidazole derivatives in good to excellent yields by reaction between hexamethyldisilazane and arylaldehydes, benzyl alcohols, benzyl halides in molten tetrabutylammonium bromide as an inexpensive and non toxic solvent has been developed. The remarkable advantages of this method are the simple workup procedure, high yields of products, the use of an ionic liquid as a green solvent, and the availability of reagents. Georg Thieme Verlag Stuttgart - New York.
- Salehi, Javad,Khodaei, Mohammad M.,Khosropour, Ahmad R.
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experimental part
p. 459 - 462
(2011/04/16)
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- Novel charge-transfer chromophores featuring imidazole as Π-linkage
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Overall 21 imidazole-based chromophores have been synthesized and fully characterized. The imidazole core was systematically substituted with donors (NMe2 and OMe) and acceptors (NO2 and CN groups) additionally separated from the imi
- Patel, Anjan,Bures, Filip,Ludwig, Miroslav,Kulhanek, Jiri,Pytela, Oldrich,Ruzicka, Ales
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experimental part
p. 999 - 1013
(2009/09/30)
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- Crystal structures and solution spectroscopy of lophine derivatives
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Lophine (2,4,5-triphenylimidazole) derivatives were synthesized and their physicochemical properties were determined. Spectroscopic and fluorescence behavior of lophine derivatives in methanol at different pH and various solvents were presented. The observed spectroscopic features in the solution are determined by specific interactions of the NH hydrogen. These kinds of interactions are manifested both in the solid state and in solution. The crystal and molecular structures of lophine derivatives with different solvents of crystallization are presented and discussed. In all solvates the solvent molecules link host molecules through hydrogen bonds.
- Fridman, Natalya,Kaftory, Menahem,Eichen, Yoav,Speiser, Shammai
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experimental part
p. 101 - 109
(2009/04/07)
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- Regioselective synthesis of cis- and trans-2,4,5-triarylimidazolines and 2,4,5-triarylimidazoles from available reagents
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Novel data were obtained concerning the reaction of aromatic aldehydes with ammonia. A preparative method for the synthesis of new substituted 1,3,5-triaryl-2,4-diazapenta-1,4-dienes was developed. These products are the starting reactants for syntheses of cis- and trans-2,4,5-triaryl-2-imidazolines and 2,4,5-triarylimidazoles.
- Lozinskaya,Tsybezova,Proskurnina,Zefirov
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p. 674 - 678
(2007/10/03)
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- Invesgations on the Influence of Halide Substituents on the Estrogen Receptor Interaction of 2,4,5-Tris(4-hydroxyphenyl)imidazoles
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Previously, we reported on the synthesis and estrogen receptor (ER) interaction of imidazoles, which had to be 1-alkyl-4,5-bis(2-halo-4-hydroxyphenyl) substituted for a high relative binding affinity (RBA > 1 %). This led to the assumption that a shielding of the polar heterocyclic system is a prerequisite for ER binding. In continuation of this study we synthesized 2,4,5-tris(4-hydroxyphenyl)imidazoles with Cl- or F-atoms in the ortho-positions of the aromatic rings and evaluated whether they mediate sufficient hydrophobicity for ER interaction. 2-(2,6-Dichloro-3/4-hydroxyphenyl)-4,5-bis(2-halo-4-hydroxyphenyl)imidazoles were synthesized by reaction of the respective methoxy-substituted benzil with either the 2,6-dichloro-4-methoxy- or the 2,6-dichloro-3-methoxybenzaldehyde in ammonium acetate solution. The required ether cleavage was performed subsequently with BBr3. In the competition experiment with [ 3H]estradiol the imidazoles with the a C2-standing (2,6-dichloro-4-hydroxyphenyl) ring showed an RBA > 0.02 %, but did not activate the luciferase gene in estrogen receptor positive MCF-7-2a breast cancer cells stably transfected with the plasmid EREwtcluc. In the test for antagonistic potency only the 2-(2,6-dichloro-4-hydroxyphenyl)-4,5-bis(4-hydroxyphenyl)imidazole 3 antagonized the effects of 1 nM estradiol slightly. From these data, it can be concluded that a C2-standing 2,6-dichloro-4-hydroxyphenyl ring is not appropriate to optimize the ER interaction of 4,5-(4-hydroxyphenyl)imidazoles.
- Gust, Ronald,Busch, Sandra,Keilitz, Roland,Schmidt, Kathrin,Von Rauch, Moriz
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p. 456 - 465
(2007/10/03)
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- A NOVEL SYNTHESIS OF 2,4,5-TRIARYLIMIDAZOLES
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Aryl cyanides were reacted with α, α-dilithioarylnitromethanes to form 2,4,5-triarylimidazoles in good yield.An unusual cyclisation - elimination mechanism is proposed for this reaction.
- Hayes, Jerome F.,Mitchell, Michael B.,Wicks, Christopher
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p. 575 - 586
(2007/10/02)
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- Preparation and antiinflammatory activity of some nonacidic trisubstituted imidazoles
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A number of trisubstituted imidazoles were made and several found to be potent antiinflammatory agents when examined in the carrageenan rat paw edema test. The antiinflammatory activity of these compounds is retained in adrenalectomized rats. Unlike many previously reported antiinflammatory agents, these compounds are extremely weak acids pK[a] ≥ 11) and are therefore not ionized at physiological pH. One compound, 4,5 bis (4 methoxyphenyl) 2 trifluoromethylimidazole (flumizole), is more potent than indometacin in the rat paw edema test and, in contrast to some related compounds, does not cause photosensitization in mice.
- Lombardino,Wiseman
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p. 1182 - 1188
(2007/10/04)
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