- Synthesis, characterization and DPPH scavenging activity of some benzimidazole derivatives
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A base-catalyzed conversion of aldehydes to benzimidazoles has been achieved. The compounds have been characterized by IR, NMR, micoranalysis, and GC-MS. The reaction for the formation of benzimidazoles has been monitored with 1H NMR and IR. Th
- Odame, Felix,Krause, Jason,Hosten, Eric C.,Betz, Richard,Lobb, Kevin,Tshentu, Zenixole R.,Frost, Carminita L.
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- Photopromoted oxidative cyclization of an o-phenylene-bridged Schiff base via a manganese(III) complex, leading to a fluorescent compound, 2-(2-hydroxyphenyl)benzimidazole
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Visible light photolysis of [N,N′-o-phenylenebis-(salicylideneaminato)]diaquamanganese(III) resulted in the fluorescent compound 2-(2-hydroxyphenyl)benzimidazole by a one electron redox reaction between MnIII and the Schiff base ligand, followe
- Fukuda, Takashi,Sakamoto, Fuminori,Sato, Minoru,Nakano, Yoshiharu,Tan, Xiang Shi,Fujii, Yuki
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- 2-(2'-Hydroxyphenyl)benzothiazoles, -benzoxazoles, and -benzimidazoles for Plastic Scintillation Applications
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A new series of fluorescent compounds has been tested as dopants for plastic scintillation applications.Several 2-(2'-hydroxyphenyl)benzothiazole, -benzoxazole, and -benzimidazole derivative have been prepared and studied in a polystyrene matrix.Each deri
- Pla-Dalmau, Anna
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- A new benzimidazole-based selective and sensitive ‘on–off’ fluorescence chemosensor for Cu2+ ions and application in cellular bioimaging
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Two new twinborn benzimidazole derivates (L and A), which bonded pyridine via the ester space on the opposite and adjacent positions of the benzene ring of benzimidazole respectively, were designed and synthesized. Compound L displayed fluorescence quench
- He, Yi,Bing, Qijing,Wei, Yingjuan,Zhang, Heyang,Wang, Guang
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- Simple naked-eye ratiometric and colorimetric receptor for anions based on azo dye featuring with benzimidazole unit
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A simple, tailor made receptor 2 based on azo dye featuring with benzimidazole unit with hybrid -OH and -NH binding sites was synthesized and characterized. The addition of CN-, AcO-, F-, and H2PO4su
- Kaur, Navneet,Dhaka, Gargi,Singh, Jasvinder
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- Structures, photoluminescence and theoretical studies of two Zn II complexes with substituted 2-(2-hydroxyphenyl)benzimidazoles
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Two new ZnII complexes of 2-(2-hydroxyphenyl)benzimidazole (Hpbm), and 5-ammo-2-(1H-benzoimidazol-2-yl)phenol (Hapbm), namely [Zn(pbm) 2] (1), and [Zn(apbm)2]· C2H 5OH·H2O (2), as well as t
- Tong, Yi-Ping,Zheng, Shao-Liang,Chen, Xiao-Ming
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- Complexes containing benzimidazolyl-phenol ligands and Ln(III) ions: Synthesis, spectroscopic studies and preliminary cytotoxicity evaluation
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Fourteen new complexes were obtained from Ln(III)(NO3)3?n-H2O and the chromophores 2-(1H-benzo[d]imidazol-2-yl)-phenol (Bzp1) or 2-(5-methyl-1H-benzo[d]imidazol-2-yl)-phenol (Bzp2). The complete characterization allowed us
- Hernández-Morales, Andrea,Rivera, José María,López-Monteon, Aracely,Lagunes-Castro, Soledad,Castillo-Blum, Silvia,Cure?o-Hernández, Karla,Flores-Parra, Angelina,Villase?or-Granados, Osvaldo,Colorado-Peralta, Raúl
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- Spectral studies on benzimidazole-based “bare-eye” probe for the detection of Ni2+: Application as a solid state sensor
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The colorimetric chemosensors for metal ion sensing containing azo group (–N[dbnd]N–) as a chromogenic signaling unit and 2-(2′-hydroxyphenyl)benzimidazole as binding unit are reported. Compound 2 and 3 were studied as metal ion chemosensors in the presen
- Dhaka, Gargi,Kaur, Navneet,Singh, Jasvinder
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- Synthesis, thermoanalysis, and thermal kinetic thermogravimetric analysis of transition metal Co(II), Ni(II), Cu(II), and Zn(II) complexes with 2-(2-Hydroxyphenyl)benzimidazole (HL)
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Four complexes with general formulas MIIL2· CH3OH (M = Co, Zn) and MIIL2 (M = Ni, Cu) were synthesized by transition metal ions MII (Co, Ni, Cu, Zn) reacting with 2-(2-hydroxyphenyl)benzimi
- Jiang, Min,Li, Jun,Huo, Yong-Qian,Xi, Yun,Yan, Jun-Feng,Zhang, Feng-Xing
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- Syntheses, crystal structures, and properties of nickel and cadmium complexes containing imidazole derivatives
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[Ni3(C13H9N2O) 5(CH3OH)2] (1) and [Cd(C12H 8N3)3] (2) were synthesized in methanol and characterized by elemental analyses, IR spectra
- Hou, Tingting,Yue, Shumei,Yue, Xiangru,Ma, Jianfang
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- Electrochemical, thermodynamic and quantum chemical studies of synthesized benzimidazole derivatives as corrosion inhibitors for N80 steel in hydrochloric acid
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The inhibitive action of synthesized benzimidazole derivatives, namely: 2-(1-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl)phenol (MBP), 2-(1-((piperazine-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenol (PzMBP) and 2-(1-((piperidine-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenol (PMBP) on corrosion of N80 steel in 15% HCl solution has been studied using weight loss measurement, potentiodynamic polarization and electrochemical impedance spectroscopy (EIS) techniques. It was found that the inhibition efficiency of all the three inhibitors increases with increase in concentration of inhibitors and decreases with increase in temperature. The inhibitors, PzMBP, MBP, and PMBP show corrosion inhibition efficiency of 96.3, 94.4 and 92.9% respectively, at 200 ppm and 303 K. Polarization studies showed that the studied inhibitors are mixed type in nature. The results of the Fourier transform infrared (FTIR) and UV-visible spectroscopy provided evidence of iron/inhibitors interactions. Scanning electron microscopy (SEM) and atomic force microscopy (AFM) were performed for surface analysis of N80 steel samples in acid solution without and with inhibitors. The Density Functional Theory (DFT) was employed for quantum chemical calculations to correlate the experimental findings.
- Yadav,Kumar,Purkait,Olasunkanmi,Bahadur,Ebenso
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- Synthesis and fluorescent properties of 2-(1H-benzimidazol-2-yl)-phenol derivatives
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A high yield one pot synthesis of 2-(2-hydroxyaryl)-1H-benzimidazole derivatives by 2-hydroxy aromatic aldehydes with aromatic 1,2-diamines in the presence of manganese(III) acetate at room temperature was developed. Nine fluorescencers 2-(2-hydroxyaryl)-1H-benzimidazoles with substituent(s) X (X = H, CH3, CH3O, Cl) and two fluorescencers 2-(2-hydroxyaryl)-1H-naphth[2,3-d]imidazoles with substituent of H or Cl were prepared in 38-87% yield and the ultraviolet absorption and fluorescent spectra of the eleven compounds synthesized were measured in methanol. The fluorescent characteristics of the 2-(2-hydroxyaryl)benzimidazole derivatives prepared were investigated on the basis of excited-state intramolecular proton transfer mechanism, Stokes' shift, quantum yield, and the relationship between fluorescent intensity and the substituents were derived.
- Ouyang, Jie,Ouyang, Chenguang,Fujii, Yuki,Nakano, Yoshiharu,Shoda, Takuji,Nagano, Tetsuo
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- Preparation, characterization, DFT calculations and ethylene oligomerization studies of iron(II) complexes bearing 2-(1H-benzimidazol-2-yl)-phenol derivatives
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Five 2-(1H-benzimidazol-2-yl)-phenol derivatives including 1H (HL1), 5-chloro-(HL2), 5-methyl-(HL3), 5,6-dichloro-(HL4), and 5,6-dimethyl-(HL5) were synthesized by the reaction of their corresponding
- Haghverdi, Marzieh,Tadjarodi, Azadeh,Bahri-Laleh, Naeimeh,Haghighi, Mehdi Nekoomanesh
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- Synthesis and characterization of binuclear manganese(IV,IV) and mononuclear cobalt(II) complexes based on 2-(2-hydroxyphenyl)-1H-benzimidazole
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The bidentate benzimidazolic hpbm (1), [2-(2-hydroxyphenyl)-1H-benzimidazole], was obtained under mild conditions, and its corresponding metal complexes, di-μ-oxo dimanganese(IV,IV) [Mn2O2(hpbm)4 · 2Py · 5H2O] (
- Duan, Ming-Yue,Li, Jun,Xi, Yun,Lue, Xiang-Fei,Liu, Jing-Zhou,Mele, Giuseppe,Zhang, Feng-Xing
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- Synthesis and evaluation of 2-aryl-1H-benzo[d]imidazole derivatives as potential microtubule targeting agents
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Microtubule targeting agents (MTAs) are the potential drug candidates for anticancer drug discovery. Disrupting the microtubule formation or inhibiting the de-polymerization process by a synthetic molecule can lead to an excellent anticancer drug candidat
- Lee, Jung-Seop,Nimse, Satish Balasaheb,Shinde, Pramod B.,Song, In-ho,Song, Keum-soo,Warkad, Shrikant Dashrath,Yeom, Gyu Seong
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- [Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)]: Synthesis, crystal structure, catalytic activity and DFT study
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Metal-organic hybrid complexes often exhibit large surface area, pore volume, fascinating structures and potential applications including catalytic applications. Hence a new metal-organic hybrid complex [Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)] was synthesized using conventional method. Physico-chemical characterization of the complex was performed with FTIR spectroscopy, single crystal X-ray diffraction, TGA, EPR and FESEM. Single crystal X-ray diffraction study suggests it to be three dimensional with space group P212121 (orthorhombic). The crystal achieves its three-dimensional structure and stability through extensive intermolecular hydrogen bonding. Hirshfeld surface analysis, catalytic activity and DFT study of the complex was also performed. The synthesized complex acts as good catalyst in benzimidazole synthesis with good recyclability as catalyst up to 5th run.
- Brahman, Dhiraj,Chhetri, Sailesh,Kamath, Amarjit,McArdle, Patrick,Sinha, Biswajit
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- Design, preparation, biological investigations and application of a benzoguanamine-based nickel complex for the synthesis of benzimidazoles
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The new magnetic-supported benzoguanamine-based nickel complex was prepared, characterized by various procedures and used as a capable heterogeneous nano-catalyst for the synthesis of diverse 2-phenyl-1H-benzo[d]imidazoles from the reaction o-phenylenedia
- Habibi, Davood,Heydari, Somayyeh,Karamian, Roya,Oliaei, Sajjad,Ranjbar, Nika
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- 1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles
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In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]
- Kalhor, Mehdi,Zarnegar, Zohre
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p. 519 - 540
(2021/12/03)
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- Synthesis of novel benzimidazoles at room temperature, under solvent-free condition and their biological studies
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Abstract: An efficient and facile synthesis of substituted novel benzimidazoles (3a–3h) mediated by fruit juices viz. Cocos nucifera L. juice, Citrus limetta juice and Citrus sinensis L. juice, via condensation of substituted aldehydes (1a–1h) and o-pheny
- Gulati, Susheel,Singh, Rajvir,Sangwan, Suman,Rana, Suprita
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p. 167 - 179
(2020/08/05)
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- s-Tetrazine-functionalized hyper-crosslinked polymers for efficient photocatalytic synthesis of benzimidazoles
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Developing green-safe, efficient and recyclable catalysts is crucial for the chemical industry. So far, organic photocatalysis has been proved to be an environmentally friendly and energy-efficient synthetic technology compared with traditional metal catalysis. As a versatile catalytic platform, hyper-crosslinked polymers (HCPs) with large surface area and high stability are easily prepared. In this report, we successfully constructed two porous HCP photocatalysts (TZ-HCPs) featurings-tetrazine units and surface areas larger than 700 m2g?1through Friedel-Crafts alkylation reactions. The rational energy-band structures and coexisting micro- and mesopores endow TZ-HCPs with excellent activities to realize the green synthesis of benzimidazoles (28 examples, up to 99% yield, 0.5-4.0 h) in ethanol. Furthermore, at least 21 iterative catalytic runs mediated by TZ-HCP1D were performed efficiently, with 96-99% yield. This study of TZ-HCPs sheds light on the wide-ranging prospects of application of HCPs as metal-free and green photocatalysts for the preparation of fine chemicals.
- An, Wan-Kai,Zheng, Shi-Jia,Zhang, Hui-Xing,Shang, Tian-Tian,Wang, He-Rui,Xu, Xiao-Jing,Jin, Qiu,Qin, Yuchen,Ren, Yunlai,Jiang, Song,Xu, Cui-Lian,Hou, Mao-Song,Pan, Zhenliang
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supporting information
p. 1292 - 1299
(2021/02/26)
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- Fluorinated phosphoric acid as a versatile effective catalyst for synthesis of series of benzimidazoles, benzoxazoles and benzothiazoles at room temperature
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The present work describes synthesis of a series of benzimidazoles, benzoxazoles and benzothiazoles through the cyclization of 1, 2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol with aryl, aliphatic and heteroaryl aldehydes. The present synthetic protocol is very much efficient in presence of 5 mol % fluorophosphoric acid as a catalyst in ethanol solvent at room temperature. Shorter reaction time, simple work-up technique, high yields and easy availability are specific compensations of the present synthetic approach.
- Mathapati, Sushil R.,Patil, Komal N.,Mathakari, Sujit S.,Suryawanshi, Appasaheb W.,Jadhav, Arvind H.
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p. 538 - 547
(2021/01/21)
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- Synthesis and fungicidal activity of novel 6H-benzimidazo[1,2-c][1,3]benzoxazin-6-ones
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[Figure not available: see fulltext.] A series of 6H-benzimidazo[1,2-c][1,3]benzoxazin-6-one derivatives were synthesized in moderate to good yield by reaction of 2-(1H-benzimidazol-2-yl)phenols with triphosgene, and the structures of the target compounds
- Jiao, Yinchun,Ma, Caixia,Tan, Yuhuan,Tang, Zilong
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p. 581 - 587
(2021/06/16)
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- Nitroarenes as versatile building blocks for the synthesis of unsymmetrical urea derivatives and N-Arylmethyl-2-substituted benzimidazoles
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In this contribution, a fast and simple method for the synthesis of unsymmetrical urea derivatives and N-arylmethyl-2-substituted benzimidazoles was developed starting from nitroarenes. The reaction of nitroarenes and phenyl isocyanate or phenyl isothiocyanate in tin (II) chloride dihydrate/choline chloride eutectic mixture afforded the expected urea and thiourea derivatives, while the reaction of different aldehydes with o-nitroaniline or 4-methoxy-2-nitroaniline shows a markedly high preference for the obtention of N-arylmethyl-2-substituted benzimidazoles over the 2-substituted analogues. This method offers a straightforward alternative to obtain the target compounds in good to excellent yields with short reaction times employing an operationally simple experimental set-up. Graphic abstract: [Figure not available: see fulltext.] A series of unsymmetrical urea and thiourea derivatives together with 1,2-disubstituted benzimidazoles are easily obtained in good yields starting from nitroarenes employing the eutectic mixture tin (II) chloride dihydrate/choline chloride as reductive reaction media.
- Rodríguez-Huerto, Paula A.,Pe?a-Solórzano, Diana,Ochoa-Puentes, Cristian
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p. 6275 - 6283
(2021/07/29)
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- The ninhydrin core as carbonyl source to access 2-(2′-hydroxyaryl)benzimidazoles exploiting the ortho selectivity of ninhydrin-phenol adducts
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Although ninhydrin is an essential analytical tool in biochemical and forensic sciences, for the past several years, it has been employed as efficient building block for diverse organic scaffolds. In the present work, the ortho selectivity of ninhydrin-phenol adducts has been exploited to obtain 2-(2′-hydroxyaryl)benzimidazoles which are well known excited state intramolecular proton transfer (ESIPT) fluorophores. Under acidic condition, 3-(2-hydroxyaroyl)isoindolin-1-one intermediate generated in situ from ninhydrin-phenol adducts was treated with o-phenylenediamine resulting benzimidazole scaffolds via a two-step one pot strategy.
- Das, Suven,Maity, Suvendu,Ghosh, Prasanta,Dutta, Arpita
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p. 2862 - 2872
(2021/08/13)
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- Cu-Mn Bimetallic Complex Immobilized on Magnetic NPs as an Efficient Catalyst for Domino One-Pot Preparation of Benzimidazole and Biginelli Reactions from Alcohols
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An efficient magnetically recyclable bimetallic catalyst by anchoring copper and manganese complexes on the Fe3O4 NPs was prepared and named as Fe3O4@Cu-Mn. It was founded as a powerful catalyst for the domino one-pot oxidative benzimidazole and Biginelli reactions from benzyl alcohols as a green protocol in the presence of air, under solvent-free and mild conditions. Fe3O4@Cu-Mn NPs were well characterized by FT-IR, XRD, FE-SEM, TEM, VSM, TGA, EDX, DLS, and ICP analyses. The optimum range of parameters such as time, temperature, amount of catalyst, and solvent were investigated for the domino one-pot benzimidazole and Biginelli reactions to find the optimum reaction conditions. The catalyst was compatible with a variety of benzyl alcohols, which provides favorable products with good to high yields for all of derivatives. Hot filtration and Hg poisoning tests from the nanocatalyst revealed the stability, low metal leaching and heterogeneous nature of the catalyst. To prove the synergistic and cooperative effect of the catalytic system, the various homologues of the catalyst were prepared and then applied to a model reaction separately. Finally, the catalyst could be filtered from the reaction mixture simply, and reused for five consecutive cycles with a minimum loss in catalytic activity and performance. Graphic Abstract: A new magnetically recyclable Cu/Mn bimetallic catalyst has been developed for domino one-pot oxidation-condensation of benzimidazole and Biginelli reactions from alcohols. [Figure not available: see fulltext.]
- Nasseri, Mohammad Ali,Rezazadeh, Zinat,Kazemnejadi, Milad,Allahresani, Ali
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p. 1049 - 1067
(2020/09/11)
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- 2-ARYLBENZIMIDAZOLES AS PPARGC1A ACTIVATORS FOR TREATING NEURODEGENERATIVE DISEASES
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A genus of compounds encompassed by formula (III) and their use is disclosed: Formula (III). The compounds activate Ppargc1a and, as a consequence, are useful for treating a variety of neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), Alzheimer's disease, Parkinson's disease, Huntington's disease, frontotemporal degeneration, dementia with Lewy bodies, motor neuron diseases, and a demyelinating disease.
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Paragraph 85; 90
(2020/03/02)
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- Synthesis of benzimidazoles by two methods (C–H functionalization and condensation reaction) catalyzed by α-zirconium hydrogen phosphate-based nanocatalyst
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In this report, two heterogeneous nanocatalysts based on α-zirconium hydrogen phosphate were applied. These heterogeneous catalysts have demonstrated the promising catalytic activity for the synthesis of 2-substituted benzimidazoles in two different methods. One of these reactions is the functionalization of the C–H bond and the formation of C–N bond, and the other reaction involves the condensation reaction between aldehydes and 1,2-phenylenediamine. The activity of both catalysts was compared in two methods, and the superior catalyst was introduced. The prepared catalysts are easily separated from the reaction mixture by centrifugation and reused several times without significant loss of activity.
- Hajipour, Abdol R.,Zakery, Saedeh,Khorsandi, Zahra
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p. 1919 - 1931
(2020/05/28)
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- Development of homogeneous polyamine organocatalyst for the synthesis of 2-aryl-substituted benzimidazole and benzoxazole derivatives
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A new polyamine was prepared by the ring opening polymerization of epichlorohydrin and properly characterized. The catalytic property of the prepared polymer was assessed by synthesizing 2-aryl-substituted benzimidazole and benzoxazole derivatives by the conjugation of o-phenylenediamine/o-aminophenol with various aromatic aldehydes in the presence of atmospheric oxygen. Significant attributes of the present synthesis include short reaction time, good to excellent yield, high purity, easy reusability, and room temperature reaction. The reaction was carried out in the absence of any metal catalyst and other cooxidants.
- Kottayil, Hiba,Machingal, Shaibuna,Parackal B., Sherly mole,Alungal M., Shebitha,Theresa, Letcy V.,Govindan, Avudaiappan,Krishnapillai, Sreekumar
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p. 3310 - 3317
(2020/07/17)
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- Solid Phase Synthesis of Biologically active Benzimidazole Derivatives Catalysed by CH3S03H-Si02 under Solvent free Condition
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A simple an expeditious method was established for the synthesis of 2-Substituted-1H-Benzimidazole derivatives at 90°C using o-phenylenediamine and different aldehydes. It has been found that a mixture of Methanesulphonic acid-Si02to be an effective catal
- Datta, Arup,Roy, Sanjay
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p. 537 - 543
(2020/07/23)
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- Synthesis of quinoxaline, benzimidazole and pyrazole derivatives under the catalytic influence?of biosurfactant-stabilized iron nanoparticles in water
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Abstract: We have reported the synthesis, characterization, and catalytic applications of amorphous iron nanoparticles (FeNPs) using aqueous leaves extract of renewable natural resource Boswellia serrata plant. Synthesized FeNPs were stabilized in situ by the addition of aqueous pod extracts of Acacia concinna as a biosurfactant (pH 3.11). The structural investigation of biosynthesized nanoparticles was performed using UV–visible spectroscopy, X-ray diffraction analysis, selected area electron diffraction, energy-dispersive X-ray spectroscopy, scanning electron microscopy, transmission electron microscopy, X-ray photoelectron spectroscopy, thermogravimetric analysis, and BET analysis. The FeNPs were amorphous in nature with average particle size ~ 19?nm and successfully employed as heterogeneous catalyst for the synthesis of quinoxaline, benzimidazole, and pyrazole derivatives in aqueous medium at ambient conditions. The FeNPs could be recycled up to five times with modest change in the catalytic activity. Graphic abstract: [Figure not available: see fulltext.].
- Arde, Satyanarayan M.,Patil, Audumbar D.,Mane, Ananda H.,Salokhe, Prabha R.,Salunkhe, Rajashri S.
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p. 5069 - 5086
(2020/09/02)
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- Oxidative NHC catalysis for base-free synthesis of benzoxazinones and benzoazoles by thermal activated NHCs precursor ionic liquid catalyst using air as oxidant
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A reusable thermal activated NHC precursor ionic liquid catalyst ([BMIm]2[WO4]) has been prepared and developed for the synthesis of nitrogen-containing heterocycles such as benzoxazinones and benzoazoles through imines activation. [BMIm]2[WO4] exhibited the good activity for the base-free condensation and oxidative NHC catalysis tandem under air atmosphere. The catalyst can be recovered and reused for at least five runs in gram scale synthesis without any decrease in catalytic activity. Furthermore, the control experiments demonstrated that the reaction involved formation of aromatic aldimines, NHC-catalyzed oxidative formation of imidoyl azoliums and intramolecular cyclization to generate the product.
- Guan, Jiali,Liu, Wei,Liu, Yuchen,Song, Zhibin,Tao, Duan-Jian,Yan, Jieying,Yuan, Jian-Jun,Zhou, Youkang
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- Exploring beta amyloid cleavage enzyme-1 inhibition and neuroprotective role of benzimidazole analogues as anti-alzheimer agents
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Beta amyloid cleavage enzyme-1 (BACE1) is the key enzyme involved in Aβ peptide formation in Alzheimer's disease pathogenesis. We intend to target this enzyme by exploring benzimidazole analogues against BACE1 as potential anti-Alzheimer agents. Docking studies were performed to determine the hydrogen bond interactions between the designed molecules and the target protein's active site. Research indicates the relationship between oxidative stress and Aβ effect in precipitating neurodegeneration; hence, the series was also studied in vitro to ascertain its neuroprotective role by performing the lipid peroxidation assay. In silico absorption, distribution, metabolism, and excretion studies were undertaken to assess the drug-like suitability of the analogues. To judge the effect of the synthesized analogues on central nervous system (CNS), toxicity and memory model studies were conducted on mice. Thus, overall results showcase analogues 11 and 14 as the most promising ones with the dual role of BACE1 inhibition and neuroprotection, along with memory retention.
- Gurjar, Archana S.,Solanki, Vivek S.,Meshram, Ankita R.,Vishwakarma, Suchita S.
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p. 864 - 873
(2019/11/14)
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- A facile and efficient synthesis of benzimidazole as potential anticancer agents
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Abstract: This study reports a simple process to synthesize and separate of 2-(substituted-phenyl) benzimidazole derivatives with high yield and efficiency. Specifically, by reacting ortho-phenylenediamines with benzaldehydes using sodium metabisulphite a
- Hoang, Thi-Kim-Dung,Huynh, Thi-Kim-Chi,Nguyen, Thanh-Danh,Nguyen, Thi-Hong-An,Tran, Ngoc-Hoang-Son
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- Synthesis of 2-(2-Hydroxyaryl)-4H-benzo[e][1,3]oxazin-4-ones by Palladium-Catalyzed C(sp2)?H Hydroxylation via Electro-chemical Oxidation
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An electrochemical direct ortho-hydroxylation of 2-aryl-4H-benzo[e][1,3]oxazin-4-ones was developed with Pd(OAc)2 as catalyst, oxazine ring as a directing group and Oxone as the hydroxylation reagent. A series of hydroxylation products were obtained under mild conditions, and the yields were from medium to good. This method is characterized by good functional group tolerance and a wide range of substrates. More importantly, use anodic oxidation to avoid the use of potentially toxic and polluting oxidants. A gram-scale direct electrochemical hydroxylation of 2-phenyl-4H-benzo[e][1,3]oxazin-4-one was performed, and the hydroxylation product was applied to synthesize the drug deferasirox. In addition, the single crystal of 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one was obtained and determined by X-ray diffraction. Finally, the reaction mechanism was proposed and verified by cyclic voltammetry (CV). This protocol also provides an alternative electrochemical hydroxylation methodology for the functionalization of molecules. (Figure presented.).
- Wu, Hongfeng,An, Qi,He, Chaoyin,Fan, Xiaodong,Guo, Weihao,Zuo, Minghui,Xu, Chunzhao,Guo, Rui,Chu, Wenyi,Sun, Zhizhong
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supporting information
p. 2459 - 2465
(2020/04/29)
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- Design and synthesis of three Fe(III) mixed-ligand complexes: Exploration of their biological and phenoxazinone synthase-like activities
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New Fe(III) complexes with mixed ligands based on 1-{(E)-[(4-methylphenyl)imino]methyl}-2-naphthol (HN) as primary ligand and secondary co-ligand of O-hydroxy quinolone (HQ), 2-(1H-benzimidazol-2-yl)phenol (HB) and 2-(4,5-diphenyl-1H-imidazol-2-yl)phenol
- Ismael, Mohamed,Abdel-Mawgoud, Abdel-Mawgoud M.,Rabia, Mostafa K.,Abdou, Aly
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supporting information
(2020/02/05)
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- Synthesis, Biological Evaluation, and Molecular Docking Studies of Some New 2-(2-(Substituted piperazin-1-yl)-phenyl)-1H-benzo[d]imidazoles as Potential Antibacterial, Anticancer, and Antifungal Agents
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Some new 2-(2-(substituted piperazin-1-yl)-phenyl)-1H-benzo[d]imidazoles (3a-3g) were designed, synthesized, and evaluated by the docking studies using glide tool for their antimicrobial and anticancer activities. The structures of these compounds were ch
- Bhardwaj, Harsh,Sharma
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p. 531 - 538
(2021/02/02)
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- Three-Way Chemoselectivity Switching through Coupled Equilibria
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Controlling the chemoselectivity of reactions operating on complex mixtures, including those found in biological and petrochemical feedstocks or in the primordial soup from which life emerged, is generally challenging. The selectivity of imine oxidation c
- Puangsamlee, Thamon,Miljani?, Ognjen ?.
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supporting information
p. 5900 - 5904
(2020/08/05)
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- Method for synthesizing benzimidazole compound through copper catalysis
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The invention relates to a method for synthesizing a benzimidazole compound by copper catalysis. The method comprises the following steps: dissolving o-phenylene diamine, benzyl alcohol or substitutedbenzyl alcohol in an organic solvent, adding a copper catalyst, carrying out reactions at a room temperature for 3-6 hours, and separating and purifying the reaction product to obtain the benzimidazole compound. Compared with the prior art, the method has the advantages of simple and green synthesis process, excellent selectivity, high yield and wide substrate range, and has great application potential in drug synthesis, natural product synthesis and the like.
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Paragraph 0044-0046
(2020/05/05)
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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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- Microwave use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds method
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The invention discloses a microwave the use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds, in the aqueous phase under microwave conditions adding benzoic amidine compound under alkaline condition [...] into benzimidazole reaction, invention an environment-friendly, the operation is simple, cheap and safe, efficient process for preparing benzimidazole method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection; .
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Paragraph 0049
(2019/03/28)
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- A nanoscopic icosahedral {Mo72Fe30} cluster catalyzes the aerobic synthesis of benzimidazoles
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In this study, the catalytic efficiency of amorphous {Mo72Fe30} nanocapsules as a safe Keplerate polyoxometalate in organic synthesis was exploited. The easy-made solid catalyst exhibited high efficiency using a very low dosage (0.02
- Garazhian, Zohreh,Rezaeifard, Abdolreza,Jafarpour, Maasoumeh
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p. 34854 - 34861
(2019/11/14)
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- A novel ternary GO@SiO2-HPW nanocomposite as an efficient heterogeneous catalyst for the synthesis of benzazoles in aqueous media
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A new solid acid catalyst, consisting of 12-phosphotungstic heteropoly acid (HPW) supported on graphene oxide/silica nanocomposite (GO@SiO2), has been developed via immobilizing HPW onto an amine-functionalized GO/SiO2 surface through coordination interaction (GO@SiO2-HPW). The GO@SiO2-HPW nanocomposite was characterized by Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and powder X-ray diffraction (XRD). The prepared nanocomposite could be dispersed homogeneously in water and further used as a heterogeneous, reusable, and efficient catalyst for the synthesis of benzimidazoles and benzothiazoles by the reaction of 1,2-phenelynediamine or 2-aminothiophenol with different aldehydes.
- Habibzadeh, Setareh,Firouzzadeh Pasha, Ghasem,Tajbakhsh, Mahmood,Amiri Andi, Nasim,Alaee, Ehsan
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p. 934 - 944
(2019/06/13)
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- Synthesis of new TCH/Ni-based nanocomposite supported on SBA-15 and its catalytic application for preparation of benzimidazole and perimidine derivatives
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A stable nickel-decorated SBA-15 nanocomposite (Ni/TCH@SBA-15) was synthesized through surface modification of silica nanoparticles with 3-chloropropyltriethoxysilane (CPTES) and thiocarbohydrazide (TCH) followed by metal–ligand coordination with Ni (II). The structure of this organometallic nanocomposite was characterized by Fourier transform-infrared, field emission-scanning electron microscopy, EDAX, transmission electron microscopy, atomic absorption spectroscopy and N2 adsorption–desorption (Brunauer–Emmett–Teller) techniques. The catalytic performance of Ni/TCH@SBA-15 (NNTS-15) was determined for the synthesis of 2-aryl-substituted benzimidazoles and 2,3-dihydroperimidines. The excellent yields within shorter reaction times, simplicity of catalytic methods, non-toxicity and clean reactions, mild reaction conditions and easy work-up procedure are the important merits of these synthetic protocols. Moreover, the Ni (II) bonded to the SBA-15 surface was stable under the catalytic reaction conditions resulting in its efficient recycling and reuse.
- Kalhor, Mehdi,Rezaee-Baroonaghi, Fahimeh,Dadras, Akbar,Zarnegar, Zohre
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- Synthesis, characterization and single crystal X-ray studies of pincer type Ni(II)-Schiff base complexes: Application in synthesis of 2-substituted benzimidazoles
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Five new pincer type Ni(II)-Schiff base complexes of the general formula [NiL1(PPh3)] 1, [NiL2(PPh3)] 2, [NiL3(PPh3)] 3, [NiL4(PPh3)] 4 and [NiL4(4-MePy)] 5
- Agrahari, Bhumika,Layek, Samaresh,Ganguly, Rakesh,Dege, Necmi,Pathak, Devendra D.
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- Organocatalytic Green Approach Towards the Fabrication of Fused Benzo N,N-containing Heterocycles Facilitated by Ultrasonic Irradiation
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The development of a metal-free protocol for transformations in organic synthesis offers a significant potential environmental benefit. This article reports the exploration of meglumine, a nontoxic and biodegradable amino sugar, as an organocatalyst for the synthesis of biologically active 1H-dibenzo[b,e][1,4]diazepin-1-ones, highly regioselective benzimidazole derivatives and derivatives of quinoxalines. Operational simplicity, mild reaction conditions, shorter reaction times, and use of green solvents are the highlights of this protocol. The advantage of ultrasonic irradiation has been significantly explored for the synthesis of the aforesaid compounds. Furthermore, the multifaceted use of o-phenylenediamine has also been accentuated in the study.
- Nongrum, Ridaphun,Kharmawlong, George Kupar,Rani, Jims World Star,Rahman, Noimur,Dutta, Arup,Nongkhlaw, Rishanlang
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- Aerobic {Mo72V30} nanocluster-catalysed heterogeneous one-pot tandem synthesis of benzimidazoles
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A novel heterogeneous one-pot protocol is developed for tandem aerobic synthesis of benzimidazoles through dehydrogenative coupling of primary benzylic alcohols and aromatic diamines co-catalysed by Keplerate-type {Mo72V30} polyoxometalate and N-hydroxyphthalimide (NHPI). The catalytic system also works well for the synthesis of benzimidazoles using benzaldehydes, as commonly used starting materials, in the absence of NHPI. The high activity of the solid nanocluster provides standard conditions avoiding current limitations of oxidation methods including high catalyst loadings. The spectral results and leaching experiments revealed that the nanocapsule preserved its structural integrity after being reused in consecutive runs.
- Khoshyan, Ashkan,Pourtahmasb, Mehrdad,Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
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- Copper(II) Oxide Nanoparticles Impregnated on Melamine-Modified UiO-66-NH2 Metal–Organic Framework for C–N Cross-Coupling Reaction and Synthesis of 2-Substituted Benzimidazoles
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A zirconium-based metal–organic framework, UiO-66-NH2, modified by melamine (Mlm) was used as a support for CuO nanoparticles (NPs). Melamine offered a platform for uniform and homogeneous distribution of NPs on the surface of the frameworks and made a strong bonding to the NPs to avoid undesirable leaching. UiO-66-NH2-Mlm/CuO NPs were used for the Buchwald–Hartwig C–N cross-coupling reaction to synthesize arylated anilines from phenyl iodide, bromide, and chloride and primary and secondary amines in DMF at 110°C. The catalyst was also employed for the synthesis of 2-substituted benzimidazole derivatives from various aromatic aldehydes and o-phenylenediamine in the absence of an oxidant in EtOH at room temperature. The catalyst was recyclable and reusable for several times and exhibited good stability (examined by BET, XRD, and SEM–EDX) in reaction conditions.
- Najari, Susan,Jafarzadeh, Mohammad,Bahrami, Kiumars
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p. 2853 - 2865
(2019/09/13)
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- Green synthesis of benzimidazole derivatives under ultrasound irradiation using Cu-Schiff base complexes embedded over MCM-41 as efficient and reusable catalysts
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We have synthesized two recoverable catalysts by covalently attaching complexes such as Cu-complex-phen and Cu-complex-bipy on MCM-41 through a greener synthetic route. FT-IR, EDX, SEM and TEM microscopy, XRD analysis, N2 adsorption and desorpt
- Bharathi, M.,Indira, S.,Induja, E.,Mahalakshmi, T.,Shamuga Bharathi, K.,Vinoth, G.
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- Synthesis, antimicrobial evaluation and molecular docking of some potential 2,6-disubstituted 1h-benzimidazoles; non-classical antifolates
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Background: Dihydrofolate reductase is one of the important enzymes for thymidylate and purine synthesis in micro-organisms. A large number of drugs have been designed to inhibit microbial DHFR but over the period of time, some drugs have developed resist
- Harer, Sunil,Bhatia, Manish,Kawade, Vikram
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p. 813 - 832
(2019/11/02)
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- Cobalt-Catalyzed Sustainable Synthesis of Benzimidazoles by Redox-Economical Coupling of o-Nitroanilines and Alcohols
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This study reveals cobalt-catalyzed sustainable synthesis of benzimidazoles by redox-economical coupling of o-nitroanilines and alcohols. The major advantage of this report is the use of a commercially available cheap cobalt catalyst to produce a wide variety of 2-substituted benzimidazoles by hydrogen autotransfer without using any additional external redox reagent and costly ligand system. A thorough mechanistic insight of the reaction is proposed by performing a series of control experiments.
- Das, Sanju,Mallick, Samrat,De Sarkar, Suman
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p. 12111 - 12119
(2019/10/02)
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- Method for catalytically synthesizing benzimidazole compound by organic protonic acid under condition of no solvent
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The invention discloses a method for catalytically synthesizing a benzimidazole compound by organic protonic acid under the condition of no solvent. According to the method provided by the invention,high efficiency catalysis is carried out to rapidly prep
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Paragraph 0015; 0042
(2018/11/27)
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- Inexpensive weight-reducing aid (L-carnitine) as an efficient catalyst for synthesis of benzimidazoles
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Aim and Objective: The benzimidazole derivatives have been obtained via weight-reducing aid (L-Carnitine) as a cheap catalyst. A wide range of aromatic aldehydes easily undergo condensations with substituted o-phenylendiamine under mild condition to affor
- Zhang, Min,Huang, Guoling,Zhang, Xuefang,Lin, Zhenyuan,Li, Yibiao,Li, Bin,Chen, Lu
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p. 567 - 570
(2019/01/14)
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- An efficient NaHSO3-promoted protocol for chemoselective synthesis of 2-substituted benzimidazoles in water
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An efficient protocol for chemoselective synthesis of 2-substituted benzimidazoles from a variety of aliphatic/aromatic/ heteroaryl aldehydes and o-phenylenediamine derivatives promoted by NaHSO3 in water had been developed. The amount of NaHSO3 had a great effect on the reaction selectivity of 2-substituted benzimidazole and 1,2-disubstituted benzimidazole when the reaction was carried out in water. When the amount of the NaHSO3 was more than 11 equivalents, the 2-substituted benzimidazole could be highly selectively formed as the sole product. NaHSO3 was firstly reacted with aldehyde to form the aldehyde sodium bisulfite, which reacted with o-phenylenediamine to form the 2-substituted benzimidazole and inhibited the formation of 1,2-disubstituted benzimidazole. This protocol solved the poor selectivity problem appearing in traditional method when cyclocondensation between o-phenylenediamine and aldehydes. The method also had advantage of simple work up by filtrating the single 2-substituted benzimidazole precipitates from reaction mixture at the end of the reaction without further purification. In addition, the method was applicable to both electron-rich and electron-poor starting materials, which was successfully used for synthesizing nine novel 2-substituted benzimidazole derivatives containing a 1,2,3-triazole moiety. They were characterized by NMR, IR and HRMS spectrum. Moreover, this method had been applied to a large scale synthesis of 2-substituted benzimidazole derivatives.
- Jiang, Yu-Qin,Jia, Shu-Hong,Li, Xi-Yong,Sun, Ya-Min,Li, Wei,Zhang, Wei-Wei,Xu, Gui-Qing
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p. 1265 - 1276
(2019/01/28)
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- A Tandem Aerobic Photocatalytic Synthesis of Benzimidazoles by Cobalt Ascorbic Acid Complex Coated on TiO2 Nanoparticles Under Visible Light
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Abstract: In this study, we developed methods for the one pot environmentally benign synthesis of benzimidazoles by cobalt ascorbic acid complex coated on TiO2 nanoparticles via aerobic photooxidative cyclization reactions. Easy work-up procedure, reusability of the catalyst and scalable to the multi-mole scale, which is valuable for an industrial process make these catalytic systems highly attractive. Also, the combination of photocatalytic and catalytic reactions presented here may help to develop a new strategy towards the development of photocatalysis-based organic synthesis. Graphical Abstract: [Figure not available: see fulltext.].
- Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
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- Highly efficient AgNO3-catalyzed approach to 2-(benzo[d]azol-2-yl)phenols from salicylaldehydes with 2-aminothiophenol, 2-aminophenol and benzene-1,2-diamine
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A new, convenient and efficient AgNO3-catalyzed strategy for the preparation of 2-(benzo[d]azol-2-yl)phenol derivatives in good to excellent yields (63–98%) is described. The reaction proceeds via condensation/intramolecular nucleophilic addition/oxidation process between substituted salicylaldehydes and 2-aminothiophenol, 2-aminophenol or benzene-1,2-diamine under mild reaction conditions. Notably, this reaction utilizes cheap AgNO3 as a readily available and low-cost benign oxidant at low catalyst loadings with excellent functional group tolerance.
- He, Xinwei,Wu, Yuhao,Jin, Wenjing,Wang, Xiaoshun,Wu, Cong,Shang, Yongjia
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- Mesoporous silica supported ytterbium as catalyst for synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzimidazoles
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The benzimidazole ring is an important pharmacophore in contemporary drug discovery. Thus, effort to identifying new compounds containing benzimidazole scaffolds have gained much attention in recent years. In the present study, MCM-41 type mesoporous silica with large pore (l-MSN) supported ytterbium was successfully prepared by wet impregnation method. Among rare earth metal salts, ytterbium triflate has already been widely investigated as a catalyst in organic synthesis but less toxic ytterbium oxide has yet to be explored. Relatively high abundance and low cost of ytterbium with respect to many catalytically active metals (e.g. Pd, Au, Ru, Ir, Pt) offer an opportunity to develop sustainable catalysts for organic conversions. The catalyst has been characterized by various techniques including nitrogen adsorption, FT-IR, TEM, SEM, EDX technique and elemental mapping. The obtained materials exhibit high surface area and a narrow distribution of mesoporosity. The catalytic performance of the Yb@l–MSNs was tested by synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzimidazoles through the coupling of aldehydes with o-phenylenediamine. The catalyst resulted in excellent yields in short reaction times and the reaction showed tolerance toward both electron-donating and electron-withdrawing functional groups at room temperature. A particularly interesting finding was the solvent selectivity of this reaction; namely, 1,2-disubstituted benzimidazoles generated as major product in water-ethanol, while the 2-substituted benzimidazoles was generated exclusively in non-polar solvents like toluene.
- Samanta, Partha Kumar,Banerjee, Rumeli,Richards, Ryan M.,Biswas, Papu
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- Preparation of 2-Arylbenzimidazole derivatives using CuO nanoparticles /H2O2 system
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CuO nanoparticles were prepared in watery lemon juice media and were characterized by XRD, FE-SEM, DLS, TGA and BET analysis. The as-prepared catalyst was efficient and recyclable for a high yielding, and practical method for the synthesis of 2-arylbenzimidazoles via cyclo-condensation reaction of 1,2-benzenediamine and aldehydes using copper oxide (CuO) nanoparticles is reported. Solvents and solvent-free effects on the reaction were investigated. Solvent plays a significant role in the reaction, and best results were achieved in solvent-free condition at 80°C. All reactions were completed in short reaction times (20–120?min) with 76–97% yields.
- Fazlinia, Abbas,Sheikh, Setareh
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p. 126 - 130
(2018/02/06)
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- Synthesis and characterization of Ni(II) complexes bearing of 2-(1H–benzimidazol-2-yl)-phenol derivatives as highly active catalysts for ethylene oligomerization
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Novel Ni(II) complexes of 2-(1H–benzimidazol-2-yl)-phenol derivatives (HLx: x = 1–5; C1–C5) have been synthesized and characterized. In the mononuclear complexes, the ligands were coordinated as bidentate, via one imine nitrogen and the phenola
- Haghverdi, Marzieh,Tadjarodi, Azadeh,Bahri-Laleh, Naeimeh,Nekoomanesh-Haghighi, Mehdi
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- One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5- b ][1,4]benzoxazepin-4(3 H)-ones by a Smiles Rearrangement
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A simple and convenient synthesis of indole-fused pyridazino[4,5- b ][1,4]benzoxazepin-4(3 H)-ones is described. A range of 2-(1 H -indol-2-yl)phenols and 4,5-dichloropyridazin-3-ones are compatible with this reaction. A Smiles rearrangement is proposed as a key step in the highly regioselective construction of the products. The easy availability of the starting materials makes this an appealing method in organic synthesis.
- Jiang, Xiaolei,Hu, Fangdong
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supporting information
p. 1207 - 1210
(2018/03/23)
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- Supported benzimidazole-salen Cu(II) complex: An efficient, versatile and highly reusable nanocatalyst for one-pot synthesis of hybrid molecules
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A novel and efficient nanocatalyst consisting of benzimidazole-salen Cu(II) complex on surface-modified silica (BS-Cu(II)@SiO2) was prepared. The heterogeneous nanocatalyst was characterized by FESEM, TEM, EDX, FT-IR, XRD, ICP, and TGA. The nanocatalyst was used for the one-pot synthesis of some target hybrid molecules. An efficient four component C–H bond activation/[3?+?2] cycloaddition and condensation/cyclization/aromatization sequence toward triazole-benzimidazole derivatives is disclosed. This methodology provides a general and rapid synthetic route to some new triazole-benzimidazole hybrids under mild reaction conditions. In addition, the heterogeneous nanocatalyst can be easily separated from the reaction mixture and used several times without noticeable leaching or loss of its catalytic activity. We believe this interesting one-pot reaction as well as benzimidazole-salen Cu(II) complex pave the way to the design and synthesis of other new hybrid molecules and metal catalysts, respectively.
- Sharghi, Hashem,Aberi, Mahdi,Shiri, Pezhman
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