- Efficient synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles in ball mill without solvent
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2-Aryl-1-arylmethyl-1H-benzimidazoles were prepared in excellent yields by the condensation of o-phenylenediamine with aldehydes under mechanically activated solvent-free conditions in ball mill using FeCl3· 6H2O as the catalyst.
- Jin, Meihong,Song, Guowei,Li, Zhenjiang,Zhou, Feng,Fan, Bo,Ouyang, Pingkai
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Read Online
- 4,5-Imidazoledicarboxylic acid immobilized on Fe3O4 magnetic nanoparticles: Preparation, characterization, and application as a recyclable and efficient nanocatalyst in the sonochemical condensation reaction
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A green synthesis of benzimidazole derivatives using recyclable magnetic 4,5-imidazoledicarboxylic is described. The magnetic 4,5-imidazoledicarboxylic (Fe3O4@ImDCA) nanocatalyst was characterized completely by infrared spectroscopy
- Shah Hosseini, Mohadesseh,Ghafuri, Hossein,Esmaili Zand, Hamid Reza
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- p-Toluenesulfonic acid coated natural phosphate as an efficient catalyst for the synthesis of 2-substituted benzimidazole
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2-Substituted benzimidazoles are selectively synthesised in high yields via the condensation of o-phenylenediamine derivatives with aldehyde derivatives using catalytic amount of p-toluenesulfonic acid coated natural phosphate (NP/PTSA) under mild conditions. The use of NP/PTSA as a reusable catalyst makes this process simple, convenient, and environmentally friendly.
- Belkharchach, Soumia,Elayadi, Hanane,Ighachane, Hana,Sebti, Said,Ali, Mustapha Ait,Lazrek, Hassan B.
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- A mild and simple one-pot synthesis of 2-substituted benzimidazole derivatives using DDQ as an efficient oxidant at room temperature
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A series of 2-substituted benzimidazoles were prepared through one-pot reaction of o-phenylenediamine with various aryl aldehydes in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in acetonitrile as solvent at room temperature. The reacti
- Naeimi, Hossein,Babaei, Zahra
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- Eco-friendly synthesis of 2-substituted benzimidazoles using air as the oxidant
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A simple, environmentally friendly procedure for the synthesis of 2-substituted benzimidazoles by the one-pot condensation of o-phenylenediamines with aromatic aldehydes using continuous bubbling of air in absolute ethanol at room temperature is described. The simplicity of the system, mild conditions, involvement of a non-toxic and practically inexhaustible oxidant, easy and quick isolation of the products, and moderate to good yields are the main advantages of this procedure.
- Chen, Guo-Feng,Shen, Hai-Dong,Jia, Hui-Ming,Zhang, Li-Yan,Kang, Hong-Yan,Qi, Qing-Qing,Chen, Bao-Hua,Cao, Jia-Li,Li, Ji-Tai
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Read Online
- Efficient (bromodimethyl)sulfonium bromide mediated synthesis of benzimidazoles
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Benzimidazoles have been efficiently synthesized in high yields by treatment of 1,2-phenylenediamine with aldehydes using (bromodimethyl)sulfonium bromide at room temperature.
- Das, Biswanath,Holla, Harish,Srinivas, Yallamalla
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Read Online
- Improved convenient and environmentally benign synthesis of biological active benzimidazoles using activated carbon and molecular oxygen
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The reaction of 1,2-phenylenediamine with a variety of aromatic aldehydes in xylenes gave the corresponding benzimidazole derivatives in good to excellent yields (82-93%) in the presence of dry activated carbon and bubbling molecular oxygen. The present r
- Tagawa, Yoshinobu,Yamagata, Kenji,Sumoto, Kunihiro
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- Visible-Light Photoredox Catalyzed Double C-H Functionalization: Radical Cascade Cyclization of Ethers with Benzimidazole-Based Cyanamides
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A visible-light photoredox catalyzed radical cascade cyclization of simple ethers with cyanamides is developed at room temperature. This strategy involves sequential inert Csp3-H/Csp2-H functionalizations through intermolecular addition reaction of oxyalkyl radicals to N-cyano groups followed by radical cyclization of iminyl radicals in situ generated with C-2 aryl rings. This method allows for efficient synthesis of tetracyclic benzo[4,5]imidazo[1,2-c]quinazolines. Importantly, this is the first example of an intermolecular-intramolecular radical cascade cyclization reaction of cyanamides.
- Jiang, Si,Tian, Xiao-Jing,Feng, Shu-Yao,Li, Jiang-Sheng,Li, Zhi-Wei,Lu, Cui-Hong,Li, Chao-Jun,Liu, Wei-Dong
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supporting information
p. 692 - 696
(2021/02/01)
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- Syntheses, characterization, and catalytic potential of novel vanadium and molybdenum Schiff base complexes for the preparation of benzimidazoles, benzoxazoles, and benzothiazoles under thermal and ultrasonic conditions
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A new ONO-tridentate Schiff base ligand (H2L) derived from 3-methoxysalicylaldehyde and nicotinic hydrazide was synthesized and characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, UV–Vis, and powder XRD studies. Then, oxovanadium(V) and dioxomolybdenum(VI) Schiff base complexes, VOL and MoO2L, were also prepared and characterized by different techniques. Moreover, the catalytic activities of both complexes were investigated for the synthesis of benzimidazoles, benzoxazoles, and benzothiazoles under reflux conditions as well as through ultrasonic irradiation. The results revealed several advantages of this procedure, including high product yields, short reaction times, facile work-up procedure, simplicity in operation, eco-friendly reaction conditions, and green aspects by avoiding toxic catalysts and solvents. Graphic abstract: [Figure not available: see fulltext.]
- Kargar, Hadi,Kargar, Khadijeh,Fallah-Mehrjardi, Mehdi,Munawar, Khurram Shahzad
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p. 593 - 605
(2021/06/21)
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- Application of sulfonic acid fabricated cobalt ferrite nanoparticles as effective magnetic nanocatalyst for green and facile synthesis of benzimidazoles
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This work represents the design and synthesis of efficient sulfonated cobalt ferrite solid acid catalyst. The synthesized solid acid green catalyst was characterized using various techniques viz. FT-IR, powder XRD, SEM, TEM and VSM. The obtained catalyst was used to synthesize biologically significant 2-substituted benzimidazole derivatives by condensation between o-phenylenediamine with various aromatic, aliphatic and heterocyclic aldehydes. High yield (up to 98 %), short reaction time (10?25 min), mild reaction condition, wide functional group tolerance, easy work-up procedure and excellent values of green chemistry metrices such as lower E factor (0.126), high RME value (88.83 %), carbon efficiency (100 %) and high atom economy (AE) value (90.65 %), are some salient features of the present catalytic system. Moreover, the catalyst recovery by simply using an external magnet and catalyst reusability up to 7 times without any significant loss in catalytic efficiency are some additional remarkable features of the current protocol.
- Yadav, Priyanka,Kakati, Praachi,Singh, Preeti,Awasthi, Satish K.
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- Copper-catalyzed radical cascade cyclization for synthesis of CF3-containing tetracyclic benzimidazo[2,1-: A] iso-quinolin-6(5 H)-ones
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Here, a general copper-catalyzed radical cascade carbocyclization reaction with 2-arylbenzoimidazoles and a Togni reagent was realized. Structurally diverse CF3-containing tetracyclic core benzimidazo[2,1-a]isoquinoline-6(5H)-ones were obtained in moderat
- Sun, Kai,Li, Guofeng,Guo, Sa,Zhang, Zhiguo,Zhang, Guisheng
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supporting information
p. 375 - 378
(2021/01/29)
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- Preparation and Characterization of New Heterogeneous Catalyst Polymer-Supported Reagent and its Application in the Green Synthesis of 2-Substituted Benzimidazoles
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A polymer-supported reagent (PSR) was synthesized by exploiting the propensity of Merrifield resin to undergo quaternization with 1-N-methylimidazole followed by anion metathesis reaction. The characterization of PSR was also made by various techniques in
- Joshi-Kulkarni, Kanchan S.,Ajalkar, Babasaheb D.,Kurane, Rajanikant M.,Jadhav, Jagnnath S.
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p. 459 - 464
(2021/02/02)
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- tert-Butyl nitrite catalyzed synthesis of benzimidazoles from o-phenylenediamine and aldehydes at room temperature
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A simple and efficient method is demonstrated for the synthesis of benzimidazoles via cyclocondensation of o-phenylenediamine with aldehydes in the presence of catalytic amount of tert-butyl nitrite. All the reactions were carried out at room temperature while the desired products were obtained in good to excellent yields.
- Azeez, Sadaf,Chaudhary, Priyanka,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Sureshbabu, Popuri
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supporting information
(2020/02/22)
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- Oxidative Radical Relay Functionalization for the Synthesis of Benzimidazo[2,1-a]iso-quinolin-6(5H)-ones
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Here, a mild and general oxidative radical relay carbocyclization reaction with 2-arylbenzoimidazoles and cyclic ethers is reported. This method provides an efficient access to a wide range of structurally diverse benzimidazo[2,1-a]isoquinoline-6(5H)-ones under metal-free conditions. The wide substrate scope, good functional group tolerance, and scale-up operation of this method are expected to promote its potential applications in biotechnology and pharmacy. (Figure presented.).
- Sun, Kai,Li, Guofeng,Li, Yuyang,Yu, Jie,Zhao, Qing,Zhang, Zhiguo,Zhang, Guisheng
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p. 1947 - 1954
(2020/03/23)
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- Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen
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Herein, an efficient and selective nickel-catalyzed dehydrogenation of five- and six-membered N-heterocycles is presented. The transformation occurs in the presence of alkyl, alkoxy, chloro, free hydroxyl and primary amine, internal and terminal olefin, trifluoromethyl, and ester functional groups. Synthesis of an important ligand and the antimalarial drug quinine is demonstrated. Mechanistic studies revealed that the cyclic imine serves as the key intermediate for this stepwise transformation.
- Banerjee, Debasis,Bera, Atanu,Bera, Sourajit
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supporting information
(2020/09/02)
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- Nanoporous Cu doped ZnS nanoparticles an efficient photo catalyst for the chemoselective synthesis of 2-substituted azoles via C-N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence in visible light
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ZnS and Cu:ZnS nanoparticles were prepared by aqueous chemical method and characterized by several analytical tools. Nanoparticles have an average size of about ~ 18 nm and possess highly open mesopores, moderate surface area, and uniform morphology. UV–vis spectra designate that doping of Cu shifted the optical response of the ZnS nanoparticles in to a visible region. These Cu:ZnS nanoparticles were employed as a photocatalyst for chemoselective synthesis of 2-substituted azoles by the reaction of benzyl bromides and 1,2-Diaminobenzene or 2-Mercaptoaniline in visible light. Analogous experiments confirmed that the reaction were proceeds through one pot C–N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence. The enhanced catalytic activity by doping could be attributed to the presence of trapping level generated by copper doping which augments the relaxation time of electron and holes so that they are easily available for the reaction. The method was also applicable for the synthesis of quinazolin-4(3H)-ones.
- Dandia, Anshu,Bansal, Sarika,Sharma, Ruchi,Kumar Mahawar, Dinesh,Rathore, Kuldeep S.,Lal Meena, Mohan,Parewa, Vijay
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- Metal-free selective synthesis of 2-substituted benzimidazoles catalyzed by Br?nsted acidic ionic liquid: Convenient access to one-pot synthesis of N-alkylated 1,2-disubstituted benzimidazoles
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A novel efficient method for the selective synthesis of 2-substituted benzimidazoles is described through condensation reaction of o-phenylenediamines with a wide rang of aliphatic, aromatic and heteroaromatic aldehyde substrates using Br?nsted acidic ionic liquid as a reusable catalyst under metal-free conditions at ambient temperature. Notably, Dodecylimidazolium hydrogen sulfate ([DodecIm][HSO4]) is the most efficient catalyst for good to excellent yields of the corresponding products (up to 98%). Subsequently, this protocol was successfully applied for the preparation of N-alkylated 1,2-disubstituted benzimidazoles in high to excellent yields via sequential one-pot reaction. In addition, catalysts are recycled at least four times without significant loss in activity.
- Senapak, Warapong,Saeeng, Rungnapha,Jaratjaroonphong, Jaray,Promarak, Vinich,Sirion, Uthaiwan
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p. 3543 - 3552
(2019/05/29)
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- Synthetic method of benzimidazole compounds
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The invention discloses a synthetic method of benzimidazole compounds. The synthetic route of the synthetic method is shown in the description. The method comprises the following steps: 1) substitutedo-phenylenediamine (I), aromatic aldehyde (II) and L-ca
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Paragraph 0088-0093
(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 novel synthesis of 2-arylbenzimidazoles in molecular sieves-MeOH system and their antitubercular activity
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Arylbenzimidazoles have been synthesized as antimycobacterial agents. An efficient synthesis has been developed for 2-arylbenzimidazoles from o-phenylenediamines and aromatic aldehydes in molecular sieves-methanol system. The methodology is straightforward to get 2-arylbenzimidazoles (3a–3z) in excellent yields with high chemoselectivity over 2-aryl-1-benzylbenzimidazoles (4a–4z). All these benzimidazole analogues were evaluated against M. tuberculosis in BACTEC radiometric assay. The compounds 4y and 4z exhibited potential antitubercular activity against M. tuberculosis H37RV, MIC at 16 μM and 24 μM respectively. The best compound of the series i.e. compound 4y was well tolerated by Swiss-albino mice in acute oral toxicity. Compound 4y possessing a diarylbenzimidazole core, can further be optimized for better activity.
- Chaturvedi, Amit K.,Verma, Amit Kumar,Thakur, Jay Prakash,Roy, Sudeep,Bhushan Tripathi, Shashi,Kumar, Balagani Sathish,Khwaja, Sadiya,Sachan, Naresh K.,Sharma, Ashok,Chanda, Debabrata,Shanker, Karuna,Saikia, Dharmendra,Negi, Arvind S.
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p. 4551 - 4559
(2018/08/11)
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- Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)-C(alkyl) Bond Cleavage
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Novel molecular iodine catalyzed cyclization reactions of 2-amino anilines with aryl alkyl ketones under oxidant and metal-free conditions are described. The reaction likely involves sequential C-N bond formation followed by C(CO)-C(alkyl) bond cleavage. Various 2-substituted benzimidazoles are obtained in moderate to good yields in a single step from readily available acetophenones, propiophenones, and phenylacetophenones.
- Ravi, Owk,Shaikh, Altab,Upare, Atul,Singarapu, Kiran Kumar,Bathula, Surendar Reddy
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p. 4422 - 4428
(2017/04/28)
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- Oxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by ortho-Quinone Catalysis
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The bioinspired ortho-quinone catalysts have been applied to heterocycles synthesis. Without any metal cocatalysts, a sole ortho-quinone catalyst enables the oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant.
- Zhang, Ruipu,Qin, Yan,Zhang, Long,Luo, Sanzhong
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supporting information
p. 5629 - 5632
(2017/10/25)
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- Experimental and theoretical approving of anomeric based oxidation in the preparation of 2-sbstituted benz-(imida, oxa and othia)-zoles using [2,6-DMPy-NO2]C(NO2)3 as a novel nano molten salt catalyst
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The synthesis of 2-sbstituted benz-(imida, oxa and othia)-zole derivatives were occurred in the presence of 2,6-dimethyl-1-nitropyridin-1-ium trinitromethanide [2,6-DMPy-NO2]C(NO2)3via the condensation reaction between 1,2-phenylenediamine or 2-aminophenol or 2-aminothiophenol and corresponding aldehyde at room temperature under solvent-free conditions respectively. [2,6-DMPy-NO2]C(NO2)3 as a nano molten salt (NMS) catalyst was fully characterized by Fourier transform infrared (FT-IR), nuclear magnetic resonance (1H NMR and 13C NMR), mass, thermal gravimetric (TG), derivative thermal gravimetric (DTG), X-ray diffraction patterns (XRD), scanning electron microscopy (SEM) and transmission electron microscopy (TEM) analysis. The described reactions are in close agreement with the green chemistry disciplines and their major advantages are good yields, short reaction time and ease of separation. Our recently new introduced concept entitled "anomeric based oxidation" was proposed for the final step of the described synthesis and it was also approved using theoretical studies.
- Zolfigol, Mohammad Ali,Khazaei, Ardeshir,Alaie, Saied,Baghery, Saeed,Maleki, Farahnaz,Bayat, Yadollah,Asgari, Asiye
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p. 58667 - 58679
(2016/07/06)
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- Lewis acidic ionic liquids of crown ether complex cations: Preparation and applications in organic reactions
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A range of Lewis acidic ionic liquids composed of crown ether complex cations were designed, synthesised and characterised by Raman, MS, FT-IR, thermogravimetric differential thermal analysis (TGA-DSC) and elemental analysis. These Lewis acidic ionic liqu
- Liang, Yatao,Wang, Jinyuan,Cheng, Chen,Jing, Huangwang
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p. 93546 - 93550
(2016/10/21)
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- Nano-Ni(II)/Y Zeolite Catalyzed Synthesis of 2-Aryl- and 2-Alkyl Benzimidazoles Under Solvent-Free Conditions
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Synthesis of some benzimidazole derivatives via condensation reaction of o-phenylenediamine derivatives with aromatic aldehydes or orthoesters under solvent-free conditions over nano-Ni(II)/Y zeolite as a heterogeneous catalyst is reported. Some advantages of this green method are easy purification, environmentally friendly conditions, low catalyst loadings, and nontoxic nature.
- Mobinikhaledi,Zendehdel,Goudarzi,Bardajee, G. Rezanejade
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p. 1526 - 1531
(2016/06/09)
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- Fe3O4@SiO2/collagen: An efficient magnetic nanocatalyst for the synthesis of benzimidazole and benzothiazole derivatives
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In this project, Fe3O4@SiO2 was synthesized and combined with collagen for the preparation of Fe3O4@SiO2/collagen. It was characterized by FT-IR, 1H NMR, VSM, XRD, EDX, SEM and T
- Ghafuri, Hossein,Esmaili, Elahe,Talebi, Majid
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p. 942 - 950
(2016/08/08)
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- Iron-catalyzed highly efficient aerobic oxidative synthesis of benzimidazoles direct from oximes in water
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This article presents a general and efficient method for aerobic oxidative synthesis of benzimidazoles from oximes catalyzed by Fe(NO3)3·9H2O under air in water. This practical method uses air as an economic and green oxidant, water as a green solvent, and tolerates a wide range of substrates that can afford the target benzimidazoles in moderate to good yields.
- Yu, Jiatao,Lu, Ming
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p. 471 - 479
(2016/04/26)
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- Rapid one pot synthesis of benzoimidazoles using MnO2 nanoparticles supported on silica as efficient oxidant agent under solvent-free conditions
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A novel one-pot and mild synthesis of benzoimidazole derivatives through the reaction of o-Phenylenediamine with aromatic aldehydes in the presence of MnO2 nanoparticles supported on silica as oxidizing agent under grinding conditions. The significant features of the present protocol are; simplicity of procedure, high products yields, purity of products, solvent-free condition, and easily work-up procedure.
- Naeimi, Hossein,Babaei, Zahra
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supporting information
p. 311 - 318
(2015/06/23)
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- Efficient aerobic oxidative synthesis of benzimidazoles with Fe(III) based PEG1000 dicationic imidazolium ionic liquid/toluene temperature-dependent biphasic system
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A green protocol for the synthesis of benzimidazoles with Fe(III) based PEG1000 dicationic imidazolium ionic liquid ([PEG1000mim2][FeCl4]2)/toluene temperature-dependent biphasic system was described. Conformed by IR analysis, FeCl4-is the dominating anion species. It could be seen that aldehydes arylamines and aromatic aldehydes bearing electron-deficient group (-Cl,-Br,-NO2) and electron-rich groups(-OH, -N(CH3)2) on the aromatic rings gave good yields (78-96%). Moreover, the Fe(III) based PEG1000 dicationic imidazolium ionic liquid could be recycled and reused without significant loss of catalytic activity after seven runs.
- Wang, Zhao-Gang,Xia, Yong-Gen,Jin, Yong,Lu, Ming
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p. 103 - 106
(2015/04/21)
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- An efficient and green synthesis of benzimidazole derivatives using SBA-15 supported cobalt nanocatalysts
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Benzimidazole derivatives have attracted a significant attention in recent years because of their medicinal applications as antiviral, antiulcer, antifungal, antihypertensive, anticancer, and antihistamine compounds. The one-pot synthesis of benzimidazole derivatives via oxidative condensation of aromatic aldehydes with o-phenylenediamines under mild conditions was successfully accomplished using a cobalt(II) supported on mesoporous silica-type material. The supported cobalt catalyst could be easily recovered after reaction completion and reused seven times with an excellent durability and without any noticeable loss in activity.
- Rajabi, Fatemeh,De, Sudipta,Luque, Rafael
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p. 1566 - 1570
(2019/11/28)
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- Iron(III) tetranitrophthalocyanine chloride immobilized on activated carbon: Efficient, excellent chemoselectivity and recyclable catalyst for synthesis of 2-substituted benzimidazoles
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The efficient and chemoselective preparation of 2-substituted benzimidazoles was established through the coupling of o-phenylenediamine with aldehydes by using iron(III) tetranitrophthalocyanine chloride immobilized on activated carbon as efficient catalyst in ethanol at room temperature. This method tolerated a variety of functional groups and had several advantages such as environmental friendliness, ease of manipulation, and a short reaction time. In addition, this catalyst can be recovered and reused for multiple cycles without loss in its catalytic activity.
- Qiu, Jun,Zhang, Yaodu,Hua, Chengwen,Gou, Xiaofeng,Chen, Bang,Zhao, Junlong
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p. 2153 - 2162
(2015/12/12)
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- Synthesis of Benzimidazoles via Iron-Catalyzed Aerobic Oxidation Reaction of Imine Derivatives with o-Phenylenediamine
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A simple and efficient protocol for preparing benzimidazoles via Fe(NO3)3.9H2O-catalyzed aerobic oxidation reaction of imine derivatives with o-phenylenediamine. This process uses air as an economical and green oxidant, tolerates a wide range of substrates, and affords the targeted benzimidazoles in moderate to excellent yields.
- Yu, Jiatao,Lu, Ming
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supporting information
p. 2148 - 2157
(2015/09/01)
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- Aerobic oxidative synthesis of benzimidazoles from amines catalyzed by 3-methyl-4-oxa-5-azahomoadamantane and iron(III) chloride
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A simple and efficient catalytic system including 3-methyl-4-oxa-5- azahomoadamantane and FeCl3 for aerobic oxidative synthesis of benzimidazoles from primary amines and o-phenylenediamine is presented. This process uses O2 as economic and green oxidant and water as green solvent, tolerates a wide range of substrates, and can afford the target products in moderate to excellent yields.
- Yu, Jiatao,Lu, Ming
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p. 10017 - 10025
(2016/01/12)
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- Aerobic oxidative synthesis of 2-arylbenzimidazoles, 2-arylbenzoxazoles, and 2-arylbenzothiazoles from arylmethanols or arylmethylamines catalyzed by Fe(III)/TEMPO under solvent-free conditions
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A simple and efficient aerobic oxidative synthesis of 2-arylbenzimidazoles, 2-arylbenzoxazoles, and 2-arylbenzothiazoles from arylmethanols or arylmethylamines with o-phenylenediamine, o-aminophenol and o-aminothiophenol catalyzed by Fe2(SO4)3/TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxyl) system under solvent-free conditions. This reaction uses air as an environmental and economic oxidant, tolerates a variety of functional groups on the aromatic ring of the benzylic partner, and affords the products in moderate yields.
- Yu, Jiatao,Shen, Mengnan,Lu, Ming
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p. 771 - 778
(2015/03/18)
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- Green and efficient methods for one-pot aerobic oxidative synthesis of benzimidazoles from alcohols with TEMPO-PEG 4000-NHC-Cu(II) complex in water
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In this article, an amphiphilic catalyst TEMPO-PEG4000-NHC-Cu(II) [2,2,6,6-tetramethylpiperidine-1-oxyl/polyethylene glycol/N-heterocyclic carbene] complex was synthesized and used as a highly efficient catalyst for one-pot aerobic oxidative synthesis of benzimidazoles from alcohols. The reactions were applicable in water with good yields in the presence of catalyst (5 mol%). Moreover, the catalyst was easily recovered from the reaction mixture and reused with almost consistent activity.
- Wang, Zhao-Gang,Cao, Xiao-Hua,Yang, Yao,Lu, Ming
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supporting information
p. 1476 - 1483
(2015/05/20)
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- A green and efficient method for synthesis of benzimidazoles using nano-Fe3O4 in PEG-400/H2O aqueous system under ambient conditions at room temperature
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In this paper, a green and facile protocol was described which was efficient for synthesis of benzimidazoles using nano-Fe3O4 catalyst with continuous bubbling of air as the oxidant in PEG-400/H 2O aqueous system at room temperature. This protocol afforded the target products in good to excellent yields and the catalytic system could be recycled and reused without significant loss of catalytic activity. Copyright
- Wang, Zhao-Gang,Zhu, Jie,Zhu, Zhou-Shuo,Xu, Jian,Lu, Ming
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p. 436 - 440
(2014/06/09)
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- [C12mim] Br: A temperature-dependent phase transfer catalyst and its application for aerobic oxidative synthesis of 2-aryl benzimidazoles, benzoxazoles or benzothiozoles catalyzed by TEMPO based ionic liquid
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The application of [C12mim]Br ionic liquid/o-xylene temperature-dependent biphasic system into the [Imim-TEMPO][Cl]/O 2-promoted condensation between o-phenylenediamines, o-aminophenol or o-aminothiophenol with aldehydes for preparing benzimidazoles, benzoxazoles or benzothiozoles is described. Several aldehydes and o-phenylenediamines, o-aminophenol or o-aminothiophenol were reacted efficiently to form corresponding products in excellent yields. Both the [Imim-TEMPO][Cl] and [C12mim]Br could be reused at least eight times without significantly decreasing the catalytic activity. The application of [C12mim]Br ionic liquid/o-xylene temperature-dependent biphasic system into the [Imim-TEMPO][Cl]/O2-promoted condensation between o-phenylenediamines, o-aminophenol or o-aminothiophenol with aldehydes for preparing benzimidazoles, benzoxazoles or benzothiozoles is described. Several aldehydes and o-phenylenediamines, o-aminophenol or o-aminothiophenol were reacted efficiently to form corresponding products in excellent yields. Both the [Imim-TEMPO][Cl] and [C12mim]Br could be reused at least eight times without significantly decreasing the catalytic activity.
- Yu, Jiatao,Lu, Ming
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p. 578 - 582
(2014/05/20)
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- Iron-catalyzed highly efficient aerobic oxidative synthesis of benzimidazoles, benzoxazoles, and benzothiazoles directly from aromatic primary amines under solvent-free conditions in the open air
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Solvent-free oxidative synthesis of benzimidazoles, benzoxazoles, and benzothiazoles from aromatic primary amines and o-phenylenediamine, o-aminophenol, and o-aminothiophenol has been achieved by using Fe(NO 3)3 and TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxyl). This reaction can use air as an economical and green oxidant, and a wide variety of derivatives were obtained in good to excellent yields. The reaction mechanism was proposed and this method provides a direct, practical, and efficient approach for the preparation of substituted benzimidazoles, benzoxazoles, and benzothiazoles.
- Yu, Jiatao,Xia, Yonggen,Lu, Ming
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supporting information
p. 3019 - 3026
(2014/10/16)
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- Oxidative coupling of o -phenylenediamine with arylmethylamines to synthesize aryl-substituted benzimidazoles under catalyst-free and solvent-free conditions
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GRAPHICAL ABSTRACT Solvent-free oxidative synthesis of benzimidazoles from arylmethylamines and o-phenylenediamine has been achieved under catalyst-free conditions. This reaction can use tert-butyl hydroperoxide (TBHP) as the oxidant, and a wide variety of derivatives were obtained in good yields. The reaction mechanism was proposed and this method provides a direct and practical approach for the preparation of substituted benzimidazoles.
- Yu, Jiatao,Lu, Ming
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p. 2520 - 2528
(2014/08/05)
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- Dehydrogenation and oxidative coupling of alcohol and amines catalyzed by organosilicon-supported TiO2@PMHSIPN
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The catalytic dehydrogenation and tandem transformation of aromatic alcohols, including oxidative coupling of alcohols and amines, were achieved successfully using a catalytic amount of organosilicon-supported titania (TiO2@PMHSIPN), which enables the efficient synthesis of aromatic aldehydes, imines, and benzimidazoles in good to excellent yields. This journal is the Partner Organisations 2014.
- Wang, Hu,Zhang, Jin,Cui, Yu-Ming,Yang, Ke-Fang,Zheng, Zhan-Jiang,Xu, Li-Wen
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p. 34681 - 34686
(2014/11/08)
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- Copper-catalyzed highly efficient aerobic oxidative synthesis of benzimidazoles, benzoxazoles and benzothiazoles from aromatic alcohols under solvent-free conditions in open air at room temperature
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Solvent-free oxidative synthesis of benzimidazoles, benzoxazoles and benzothiazoles from aromatic alcohols and o-phenylenediamine, o-aminophenol and o-aminothiophenol has been achieved by using CuCl, 2,2′-bipyridine and TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl). The reaction proceeds via a dehydrogenation in open air at room temperature, and a wide variety of derivatives were obtained in good to excellent yields. The reaction mechanism was proposed and this method provides a mild and efficient access to substituted benzimidazoles, benzoxazoles and benzothiazoles. Copyright
- Yu, Jiatao,Xu, Jian,Lu, Ming
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p. 606 - 610
(2013/10/21)
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- Rare-earth metal chlorides as efficient catalysts for the simple and green synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzothiazoles under ultrasound irradiation
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Under solvent-free and ultrasonic irradiation conditions, efficient methods for the synthesis of 1,2-disubstitued benzimidazoles and 2-substitued benzothiazoles by employing rare-earth metal chlorides as catalysts are described. The methods have the advan
- Zhang, Li-Jun.,Xia, Jing,Zhou, Yong-Qing,Wang, Hua,Wang, Shao-Wu.
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experimental part
p. 328 - 336
(2011/11/12)
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- One-pot synthesis of 2-substituted benzimidazoles catalyzed by anhydrous FePO4
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Anhydrous FePO4 has been employed as a catalyst for efficient synthesis of 2-substituted benzimidazoles. Simple and convenient procedure, easy purification and shorter reaction time are the advantages of this method, resulting in several known and three new compounds.
- Behbahani, Farahnaz K.,Ziaei, Parisa
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p. 1011 - 1017
(2013/03/13)
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- Ni nanoparticles: Mild and efficient catalyst for the chemoselective synthesis of 2-arylbenzimidazoles, 2-arylbenzothiazoles, and azomethines
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(Chemical Equation Presented) A new and efficient method has been developed for the synthesis of biologically significant 2-arylbenzimidazoles, 2-arylbenzothiazoles, and azomethines using recyclable and inexpensive polyvinyl pyrrolidone (PVP)-stabilized Ni nanoparticles in ethylene glycol at room temperature in excellent yields. Copyright Taylor & Francis Group, LLC.
- Khurana, Jitender M.,Sneha,Vij, Kanika
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experimental part
p. 2606 - 2616
(2012/08/08)
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- An Efficient and inexpensive synthesis of 2-substituted benzimidazoles in water using boric acid at room temperature
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2-Substituted benzimidazoles have been synthesized in a one-pot reaction from o-phenylenediamine and aldehydes in the presence of boric acid in water at room temperature. The method was proved to be eco-friendly, convenient and the products were isolated with good yields.
- Karimi-Jaberi, Zahed,Amiri, Mohammad
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experimental part
p. 167 - 170
(2012/06/01)
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- One-pot synthesis of imidazole derivatives under solvent-free condition
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A convenient and environment-friendly solvent-free procedure has been developed for one-pot synthesis of imidazole derivatives. On comparing the new method with the classical reaction condition, this new synthetic method shows many advantages such as high
- Zhang, Qiu-Gen,Xie, Yu,Hu, Jin-Gang,Liu, Jin-Mei,Wang, Juan,Zhong, Rong,Gao, Yun-Hua
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experimental part
p. 4611 - 4613
(2012/08/28)
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- Synthesis and SAR investigations of novel 2-arylbenzimidazole derivatives as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists
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Compounds containing 2-arybenzimidazole ring systems linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of structure-activity relationship studies led to the identification of compound 4c as a potent MCH-R1 antagonist (IC50 = 1 nM). This compound also has good metabolic stability, and favorable pharmacokinetic and brain penetration properties. However 4c was found to be potent inhibitor of the hERG potassium channel.
- Lim, Chae Jo,Kim, Nakjeong,Lee, Eun Kyoung,Lee, Byung Ho,Oh, Kwang-Seok,Yoo, Sung-Eun,Yi, Kyu Yang
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supporting information; experimental part
p. 2309 - 2312
(2011/05/15)
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- Mild and efficient synthesis of benzimidazole using lead peroxide under solvent-free conditions
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Benzimidazole derivatives have been synthesized using a catalytic amount of lead peroxide (PbO2) at room temperature with excellent yields. The remarkable selectivities under mild, neutral and solvent-free conditions and use of a commercially available, inexpensive catalyst are attractive features of this method. Copyright
- Patil, Vishvanath D.,Patil, Jaymala,Rege, Priyanka,Dere, Ganesh
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experimental part
p. 58 - 62
(2011/03/19)
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- Synthesis of 2-Substituted benzimidazoles catalyzed by FeCl 3/Al2O3 under ultrasonic irradiation
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2-substituted benzimidazoles have been synthesized in a single pot from aromatic aldehydes and ophenylenediamine catalyzed by FeCl3/Al 2O3 in DMF under ultrasonic irradiation and afforded good yields in a short period of t
- Chen, Guo-Feng,Dong, Xiao-Yun,Meng, Fan-Zhu,Chen, Bao-Hua,Li, Ji-Tai,Wang, Shu-Xiang,Bai, Guo-Yi
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experimental part
p. 464 - 469
(2012/04/23)
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- An efficient synthesis of 2-arylbenzimidazoles from o-phenylenediamines and arylaldehydes catalyzed by Fe/CeO2-ZrO2 nano fine particles
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75% Fe/CeO2-ZrO2 nano fine particles (0.005 mol%) are reported as a new catalyst for the efficient synthesis of 2-arylbenzimidazoles. A simple and convenient procedure, easy purification and shorter reaction times are the advantageous features of this method. Springer-Verlag 2011.
- Behbahani, Farahnaz K.,Ziaei, Parisa,Fakhroueian, Zahra,Doragi, Neda
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experimental part
p. 901 - 906
(2012/01/06)
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- Selective synthesis of 2-aryl-1-benzylated-1H-benzimidazoles
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An efficient and simple procedure was developed for the green synthesis of various 2-aryl-1-ben-zylated-1H-benzimidazoles in high yields by condensation of o-phenylenediamine with aldehydes with P2O5/SiO 2 as catalyst unde
- Shaterian, Hamid Reza,Fahimi, Nafiseh,Azizi, Kobra
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scheme or table
p. 2389 - 2393
(2012/02/04)
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