14691-35-1Relevant articles and documents
p-TSA catalyzed synthesis of 2,4,5-triarylimidazoles from ammonium heptamolybdate tetrahydrate in TBAI
Khodaei, Mohammad Mehdi,Bahrami, Kiumars,Kavianinia, Iman
, p. 829 - 833 (2007)
A one-pot synthesis of 2,4,5-trisubstituted imidazoles from 1,2-diketone or α-hydroxy ketone, aldehyde and ammonium heptamolybdate tetrahydrate in an inexpensive and readily available ionic liquid, tetrabutylammonium iodide (TBAI) in molten state using catalytic amounts of p-TSA has been described.
On the fluorescent, steric and electronic factors affecting the detection of metallic ions using an imidazolyl-phenolic derived fluorescent probe
Orf?o, Ronaldo B.,De Carvalho, Fabrício,Homem-De-Mello, Paula,Bartoloni, Fernando H.
, p. 1896 - 1904 (2017)
The imidazolyl-phenolic probe used at the present study has its photophysic properties regulated by a tautomeric equilibrium. After the absorption of a photon, an excited state intramolecular proton transfer process generates a ketonic species, responsibl
One-step synthesis of 2-aryl-4,5-diphenylimidazoles under microwave irradiation
Zhou, Jian-Feng,Song, Yuan-Zhi,Yang, Yan-Ling,Zhu, Yu-Lan,Tu, Shu-Jiang
, p. 1369 - 1373 (2005)
A series of 2-aryl-4,5-diphenylimidazoles were synthesized by a one-step condensation reaction of benzil, aromatic aldehyde, and ammonium acetate in acetic acid under microwave irradiation. The reactions were completed in 4-11 min with good yields and easy workup. Copyright Taylor & Francis, Inc.
Design and development of a novel cellulose/γ-Fe2O3/Ag nanocomposite: A potential green catalyst and antibacterial agent
Maleki, Ali,Movahed, Hamed,Paydar, Reza
, p. 13657 - 13665 (2016)
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.
KSF supported 10-molybdo-2-vanadophosphoric acid as an efficient and reusable catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazole derivatives under solvent-free condition
Chavan, Laxmikant D.,Shankarwar, Sunil G.
, p. 1054 - 1059 (2015)
The one-pot three-component cyclocondensation has been developed involving the reaction of benzil with an aromatic aldehydes and ammonium acetate under thermal solvent-free conditions in the presence of a KSF supported 10-molybdo-2-vanadophosphoric acid catalyst. 10-Molybdo-2-vanadophosphoric acid was immobilized on KSF with a 20% loading, which showed the highest catalytic activity. The catalyst was fully characterized using FT-IR spectroscopy, thermal analysis, XRD and SEM analysis techniques. There are several distinct advantages to this protocol, including high yields, short reaction time, operational simplicity and a recyclable catalyst with a facile work-up procedure.
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
Khodamorady, Minoo,Ghobadi, Nazanin,Bahrami, Kiumars
, (2021)
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.
Organocatalyzed Solvent Free and Efficient Synthesis of 2,4,5-Trisubstituted Imidazoles as Potential Acetylcholinesterase Inhibitors for Alzheimer's Disease
Ashraf, Muhammad,Khan, Muhammad Asim,Liu, Xiao,Mutahir, Sadaf,Pervaiz, Sania,Tariq, Sidrah,Ullah, Islam,Zhou, Bao-Jing
, (2020)
The catalytic potential of pyridine-2-carboxlic acid has been evaluated for efficient, green and solvent free synthesis of 2,4,5-trisubstituted imidazole derivatives 3a–3m. The compounds 3a–3m were synthesized by one pot condensation reaction of substituted aromatic aldehydes, benzil, and ammonium acetate in good to excellent yields (74–96 %). To explore the potential of these compounds against Alzheimer's disease, their inhibitory activities against acetylcholinesterase (AChE) were evaluated. In this series of compounds, compound 3m, bearing one ethoxy and a hydroxy group on the phenyl ring on 2,4,5-trisubstituted imidazoles, proved to be a potent AChE inhibitor (102.56±0.14). Structure–activity relationship (SAR) of these compounds was developed. Molecular dockings were carried out for the compounds 3m, 3e, 3k, 3c, 3a, 3d, 3j, and 3f in order to further investigate the binding mechanism. The inhibitor molecule was molecularly docked with acetylcholinesterase to further study its binding mechanism. The amino group of the compound 3m forms an H-bond with the oxygen atom of the residue (i. e., THR121) which has a bond length of 3.051 ?.
Synthesis and luminescence-structure relationship of 2,4,5-triarylimidazoles
Yue, Shu-Ning,Wan, Yu,Ye, Ling,Zhang, Wen-Li,Cui, Hao,Zhang, Li-Zhuo,Zhou, Qiu-Ju,Zou, Huan,Liu, Zhen-Tao,Zhao, Ling-Ling,Zhou, Sheng-Liang,Wu, Hui
, p. 6328 - 6330 (2014)
2,4,5-Triarylimidazoles were efficiently synthesized with excellent yields (90-96%) via the one-pot concentration of benzil, aromatic aldehyde and ammonium acetate in ionic liquid [BMIM][BF4] in the present of acetic acid. The luminescence-structure relationship of products was investigated.
Aicd-base behavior, electrochemical properties and DFT study of redox non-innocent phenol-imidazole ligands and their Cu complexes
Parween, Arfa,Mandal, Tarun Kanti,Guillot, Régis,Naskar, Subhendu
, p. 34 - 46 (2015)
Abstract Three Cu complexes (1, 2, 3) with N, O donor ligands having imidazole-phenol moieties 2-(4,5-diphenyl-1H-imidazol-2-yl)phenol (L1H), 4-bromo 2-(4,5-diphenyl-1H-imidazol-2-yl)phenol (L2H) and 1-(4,5-diphenyl-1H-imidazol-2-yl)
Electro-organic synthesis of 2-(4,5-diphenyl-1H-imidazol-2-yl)phenol in Aqueous medium for organic monomer based Supercapacitor electrode
Elanthamilan,Sarala,Bella,Sathiyan,Sharmila Lydia,Sundar Manoharan,Princy Merlin
, p. 32 - 42 (2017)
An efficient cost-effective and eco-friendly electro-organic synthesis of 2-(4,5-diphenyl-1H-imidazol-2-yl)phenol (DIP) in aqueous medium and its application as an electrode material for supercapacitor are reported here. The as-synthesized derivative was
Synthesis, Characterization, Modeling, and Antimicrobial Activity of FeIII, CoII, NiII, CuII, and ZnII Complexes Based on Tri-substituted Imidazole Ligand
Ismael, Mohamed,Abdou, Aly,Abdel-Mawgoud
, p. 1203 - 1214 (2018)
The reaction of the synthesized 2-(4,5-diphenyl-1H-imidazol-2-yl) phenol, (HL) ligand with FeIII, CoII, NiII, CuII, and ZnII ions at room temperature resulted in the formation of the five complexes; [Fe(L)2(H2O)(Cl)]·2H2O and [M(L)2)]·nH2O [M = Co, Zn (n = 2), Ni, Cu (n = 1)]. The ligand and its complexes were characterized based on elemental analyses, spectral, magnetic and molar conductance measurements. The molecular and electronic structure of the ligand and its complexes was optimized theoretically and the quantum chemical parameters were calculated. The results revealed an interesting geometrical variation; octahedral for FeL, seesaw for CoL, distorted square planar for NiL and CuL, as well a tetrahedral arrangement for ZnL. The HL ligand and its metal complexes were screened against the growth of pathogenic bacteria [Escherichia coli (G–) and Bacillus cereus (G+)] and fungi (Aspergillus fumigatus) in terms of the minimum inhibitory concentration (MIC). The metal complexes showed high enhancement as antimicrobial candidates with? lower MIC values compared with their parent ligand. Structure activity relationship formula was quantified by correlating the experimental MIC values with theoretical electronic chemical properties. Molecular docking of the complexes against CYP51B protein of A. fumigatus, the target enzyme for the antimicrobial reagents, was achieved to find the best orientation of the substrate, which would form a stable complex with overall minimum energy. The docking results enhanced the activity of the imidazole-based complexes as promising antimicrobial candidates.
Efficient elemental iodine catalyzed one-pot synthesis of 2,4,5-triarylimidazoles
Kidwai, Mazaahir,Mothsra, Poonam,Bansal, Vikas,Goyal, Ritu
, p. 1189 - 1194 (2006)
Elemental iodine is used as an efficient catalyst for the synthesis of 2,4,5-triarylimidazoles in excellent yields via condensation of benzoin, ammonium acetate, and aromatic aldehydes. This is a simple, one-pot, high yielding technique using cheap, non-toxic iodine in catalytic amounts.
One-pot synthesis of 2,4,5-trisubstituted imidazoles using [BPy]H 2PO4, an efficient and recyclable catalyst
Zhang, Yuliang,Zhou, Zhongqiang
, p. 189 - 196 (2013)
[BPy]H2PO4 was easily prepared and used as an efficient and recyclable catalyst for the one-pot synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions in good to excellent yields. Solvent-free conditions, simple experimental and workup procedures, and the use of a nontoxic, recyclable catalyst of an environmentally benign nature are remarkable features of the procedure.
Magnetic horsetail plant ash (Fe3O4@HA): a novel, natural and highly efficient heterogeneous nanocatalyst for the green synthesis of 2,4,5-trisubstituted imidazoles
Hosseini Mohtasham, Nina,Gholizadeh, Mostafa
, p. 2507 - 2525 (2021/03/24)
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.]
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
Vinoth, Govindasamy,Indira, Sekar,Bharathi, Madheswaran,Archana, Govindhasamy,Alves, Luis G.,Martins, Ana M.,Shanmuga Bharathi, Kuppannan
, (2020/11/16)
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.
