- Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite
-
Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.
- Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Ye, Dongdong,Wang, Dawei
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supporting information
p. 266 - 270
(2021/08/06)
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- Transition-Metal-Free Transfer Hydrogenative Cascade Reaction of Nitroarenes with Amines/Alcohols: Redox-Economical Access to Benzimidazoles
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This report describes an efficient transition-metal-free process toward the transfer hydrogenative cascade reaction between nitroarenes and amines or alcohols. The developed redox-economical approach was realized using a combination of KOtBu and Et3SiH as reagents, which allows the synthesis of benzimidazole derivatives via σ-bond metathesis. The reaction conditions hold well over a wide range of substrates embedded with diverse functional groups to deliver the desired products in good to excellent yields. The mechanistic proposal has been depicted on the basis of a series of control experiments, mass spectroscopic evidence which is well supported by density functional theory (DFT) calculations with a feasible energy profile.
- Gujjarappa, Raghuram,Kabi, Arup K.,Malakar, Chandi C.,Musib, Dulal,Roy, Anupam,Sahoo, Abhishek,Singh, Virender,Vodnala, Nagaraju
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p. 14597 - 14607
(2021/11/12)
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- Vanadyl Acetylacetonate-Copper (II) Trifluoro Methane Sulfonate Catalyzed Eco-friendly Synthesis of Substituted Benzimidazoles in Aqueous Media
-
Various substituted benzimidazoles have been successfully synthesized in aqueous medium by developing VO(acac)2–Cu(OTf)2 catalytic system. A green synthetic protocol has been created in presence of water and cetyltrimethyl ammonium bromide (CTAB) system in an organic solvent free condition. This chemoselective cyclocondensation cumoxidation process occurred in aqueous media. In this suitable method easily synthesized 2-Substituted benzimidazoles with good yields and no 1,2-disubstituted by-products were noticed. Excellent yields, environmentally benign and mild reaction condition, easy purification of the desired products are the main attractive features of this newly devised method.
- Halder, Samiran
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p. 687 - 694
(2020/11/25)
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- Copper-Mediated Diamination of Arylboronic Acids for the Synthesis of 2-Aryl Benzimidazoles Using Trimethylsilyl Azide as the Amino Sources with Aldehydes
-
A direct and versatile copper-mediated three-component reaction of arylboronic acids, trimethylsilyl azide and aldehydes for the synthesis of benzimidazoles is reported. The reaction is well tolerated by a wide range of substituted aromatic aldehydes and aromatic boronic acids to produce the corresponding benzimidazoles in moderate to high yields. Mechanism investigations demonstrated that copper-promoted Chan-Evans-Lam coupling, C?H amination, and oxidative cycloaddition are involved in the tandem processes. (Figure presented.).
- Xie, Zeqiang,Zhou, Fengtao,Ding, Ke
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supporting information
p. 3442 - 3446
(2020/07/30)
-
- "Metal-Free" Nanoassemblies of AIEE-ICT-Active Pyrazine Derivative: Efficient Photoredox System for the Synthesis of Benzimidazoles
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Supramolecular nanoassemblies of an AIEE-ICT-active pyrazine derivative (TETPY) having strong absorption in the visible region and excellent transportability have been utilized as an efficient photoredox catalytic system for the synthesis of a variety of benzimidazoles having electron-withdrawing/electron-releasing/aliphatic groups under "metal-free"conditions. The reaction protocol involves the successful harvesting of visible light by TETPY assemblies to catalyze the coupling of o-phenylenediamine/substituted diamines and substituted aromatic/heterocyclic/aliphatic aldehydes under aerial conditions using mixed aqueous media as the reaction solvent. TETPY assemblies could activate aerial oxygen to generate superoxide for completing the vital proton abstraction step without the need for any external metal/base/oxidant. Moreover, all the products are purified by recrystallization from organic solvents. The TETPY assemblies also exhibited high efficiency in catalyzing the synthesis of 2-substituted benzothiazoles and quinazolines in excellent yields.
- Dadwal, Shruti,Kumar, Manoj,Bhalla, Vandana
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p. 13906 - 13919
(2020/11/20)
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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)
-
- Synthesis, bioevaluation and docking studies of some 2-phenyl-1H-benzimidazole derivatives as anthelminthic agents against the nematode Teladorsagia circumcincta
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Gastrointestinal nematode infections are the main diseases in herds of small ruminants. Resistance to the main established drugs has become a worldwide problem. The purpose of this study is to obtain and evaluate the in vitro ovicidal and larvicidal activity of some 2-phenylbenzimidazole derivatives on susceptible and resistant strains of Teladorsagia circumcincta. Compounds were prepared by known procedures from substituted o-phenylenediamines and arylaldehydes or intermediate sodium 1-hydroxyphenylmethanesulfonate derivatives. Egg Hatch Test (EHT), Larval Mortality Test (LMT) and Larval Migration Inhibition Test (LMIT) were used in the initial screening of compounds at 50 μM concentration, and EC50 values were determined for the most potent compounds. Cytotoxicity evaluation of compounds was conducted on human Caco-2 and HepG2 cell lines to calculate their Selectivity Indexes (SI). At 50 μM concentration, nine out of twenty-four compounds displayed more than 98% ovicidal activity on a susceptible strain, and four of them showed more than 86% on one resistant strain. The most potent ovicidal benzimidazole (BZ) 3 showed EC50 = 6.30 μM, for the susceptible strain, while BZ 2 showed the lowest EC50 value of 14.5 μM for the resistant strain. Docking studies of most potent compounds in a modelled Teladorsagia tubulin indicated an inverted orientation for BZ 1 in the colchicine binding site, probably due to its fair interaction with glutamic acid at codon 198, which could justify its inactivity against the resistant strain of T. circumcincta.
- Escala, Nerea,Valderas-García, Elora,Bardón, María álvarez,Gómez de Agüero, Verónica Castilla,Escarcena, Ricardo,López-Pérez, José Luis,Rojo-Vázquez, Francisco A.,San Feliciano, Arturo,Bala?a-Fouce, Rafael,Martínez-Valladares, María,Olmo, Esther del
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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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- 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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- 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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- Transcriptome analysis predicts mode of action of benzimidazole molecules against Staphylococcus aureus UAMS-1
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Antimicrobial drug resistance is one of the most critical problems that plagued the human race in modern times. Discovery of novel antibiotics is important to counter this threat. Accordingly, herein we have reported the discovery of substituted benzimidazole class of molecules with antimicrobial property (specifically against Staphylococcus aureus). They were initially identified through a random screening and a novel catalytic synthetic strategy was utilized to access them. in vitro screening and phenotypic profiling revealed the antimicrobial nature. De novo transcriptome and gene analyses predicted the putative targets. This work provides a solid foundation for developing the benzimidazoles as a target specific antimicrobial preclinical candidate.
- Chauhan, Deepika,Hati, Santanu,Priyadarshini, Richa,Sen, Subhabrata
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p. 490 - 503
(2019/06/20)
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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 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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- Air-stable Ruthenium(II)-NNN Pincer Complexes for the Efficient Coupling of Aromatic Diamines and Alcohols to 1H-benzo[d]imidazoles with the Liberation of H2
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Two new phosphine-free RuII-NNN pincer complexes ([RuCl(L1)(CH3CN)2]Cl (1) and [RuCl(L2)(CH3CN)2]Cl (2) [L1=2,6-bis(1H-imidazole-2-yl)pyridine, L2=2,6-bis(1-hexyl-1H-imidazole-2-yl)pyridine] were synthesized to catalyze the condensation of benzyl alcohol and benzene-1,2-diamine homogeneously to 2-pheny-1H-benzo[d]imidazole and H2. The reactivity in the order of 1>2 is lower than that of the phosphine-containing RuII-NNN pincer complex [RuCl2(L1)(PPh3)3] (3), and thus a homogeneous system that contained 1, 1 equivalent of 1,2-bis(diphenylphosphanyl)ethane, and 10 equivalents of NaBPh4 was developed to improve the catalytic efficiency for the condensation of primary alcohols and benzene-1,2-diamine (or its derivatives) to 2-substituted 1H-benzo[d]imidazoles in excellent yields (up to 97 %) and turnover numbers (388). This system can be used to realize the facile one-step synthesis of 1H-benzo[d]imidazole derivatives from alcohols without the use of an oxidant and/or a stoichiometric amount of inorganic base that is usually necessary in homogeneous systems reported previously.
- Li, Lin,Luo, Qi,Cui, Huahua,Li, Renjie,Zhang, Jing,Peng, Tianyou
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p. 1607 - 1613
(2018/02/28)
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- Zn3(BTC)2 as a Highly Efficient Reusable Catalyst for the Synthesis of 2-Aryl-1H-Benzimidazole
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Zn3(BTC)2 metal-organic frameworks as recyclable and heterogeneous catalysts were effectively used to catalyze the synthesis of benzimidazole derivatives from o-phenylendiamine and aldehydes in ethanol. This method provides 2-aryl-1H
- Sajjadifar, Sami,Arzehgar, Zeinab,Ghayuri, Azadeh
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p. 205 - 211
(2017/11/13)
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- Selective Synthesis of 2-Substituted and 1,2-Disubstituted Benzimidazoles Directly from Aromatic Diamines and Alcohols Catalyzed by Molecularly Defined Nonphosphine Manganese(I) Complex
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Herein, we present a selective synthesis of 2-substituted and 1,2-disubstituted benzimidazoles by acceptorless dehydrogenative coupling of aromatic diamine with primary alcohols. The reaction is catalyzed by a phosphine-free tridentate NNS ligand-derived manganese(I) complex.
- Das, Kalicharan,Mondal, Avijit,Srimani, Dipankar
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p. 9553 - 9560
(2018/07/21)
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- Br?nsted acid-catalyzed metal-free one-pot synthesis of benzimidazoles via [4+1] heteroannulation of ortho-phenylenediamines with β-oxodithioesters
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An operationally simple and user-friendly one-pot domino protocol for the synthesis of 2-aryl/hetaryl benzimidazoles has been devised from easily available and inexpensive 1,2-phenylenediamines and β-oxodithioesters. The strategic [4+1] heteroannulation i
- Srivastava, Abhijeet,Shukla, Gaurav,Yadav, Dhananjay,Singh, Maya Shankar
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- Tunable Triazole-Phosphine-Copper Catalysts for the Synthesis of 2-Aryl-1H-benzo[d]imidazoles from Benzyl Alcohols and Diamines by Acceptorless Dehydrogenation and Borrowing Hydrogen Reactions
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Triazole-phosphine-copper complexes (TAP?Cu) have been synthesized and applied as tunable and efficient catalysts for the selective synthesis of fluoro-substituted 2-aryl-1H-benzo[d]imidazole and 1-benzyl-2-aryl-1H-benzo[d]imidazole derivatives from simple alcohols in only one step. TAP?Cu exhibited excellent and tunable catalytic activity for both dehydrogenation and borrowing hydrogen reactions with more than 80 examples being demonstrated for the first time. It was observed that the ligand played a critical role in catalyst activity. Mechanistic studies and deuterium labeling experiments indicated that the reactions proceeded by an initial and reversible alcohol dehydrogenation resulting in a copper hydride intermediate. This was also supported by the direct observation of a diagnostic copper hydride signal by solid-state infrared spectroscopy. The TAP?Cu-H complex showed absorptions at 912 cm?1 that could be assigned to copper?hydride stretches. Furthermore, the direct trapping of an intermediate bisimine was also successfully performed. (Figure presented.).
- Xu, Zhaojun,Wang, Duo-Sheng,Yu, Xiaoli,Yang, Yongchun,Wang, Dawei
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supporting information
p. 3332 - 3340
(2017/10/06)
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- Direct conversion of alkyl halides into benzimidazoles using pyridine-N-oxide and 1,2-diaminobenzenes
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Benzimidazole heterocycles were obtained from halogenated compounds and aromatic 1,2-diamines. A mild oxidizing reagent such as pyridine N-oxide (PyO) is required to produce the benzimidazole core. The method is solvent free and provides products without the need for chromatography. Good yields, moderate reaction temperature, fast reaction rates are important advantages of this procedure. {figure presented}.
- Bratulescu, George
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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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- Design, synthesis, α-glucosidase inhibitory activity, molecular docking and QSAR studies of benzimidazole derivatives
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In this study the green, one-pot, solvent-free and selective synthesis of benzimidazole derivatives is reported. The reactions were catalyzed by ZnO/MgO containing ZnO nanoparticles as a highly effective, non-toxic and environmentally friendly catalyst. T
- Dinparast, Leila,Valizadeh, Hassan,Bahadori, Mir Babak,Soltani, Somaieh,Asghari, Behvar,Rashidi, Mohammad-Reza
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- Accessing Benzimidazoles via a Ring Distortion Strategy: An Oxone Mediated Tandem Reaction of 2-Aminobenzylamines
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An exceptional oxone mediated tandem transformation of 2-aminobenzylamines to 2-substituted benzimidazoles is reported. It occurs at room temperature with aromatic, heteroaromatic, and aliphatic aldehydes. In this reaction initial condensation of 2-aminobenzylamine with appropriate aldehydes afforded a tetrahydroquinazoline intermediate which underwent oxone-mediated ring distortion to afford the desired compounds in moderate to excellent yields.
- Hati, Santanu,Kumar Dutta, Pratip,Dutta, Sanjay,Munshi, Parthapratim,Sen, Subhabrata
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supporting information
p. 3090 - 3093
(2016/07/14)
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- Method for synthesizing benzimidazole compound
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The invention relates to a method for synthesizing a benzimidazole compound shown in the formula (III). The method includes the steps that in a composite solvent, under existence of a bi-component catalyst, an assistant and NaHS, a formula (I) compound and a formula (II) compound are reacted, reacting is completed, then the mixture is posttreated, and therefore the formula (III) compound is obtained (please see the specification); R1 is selected from H or C1-C6 alkyl, R2 is selected from H or C1-C6 alkyl or halogen, and X is halogen. According to the method, as specific reaction substrates are used, and a comprehensive reaction system formed by the catalyst, the assistant, alkali, a solvent and the like is used, the target product with the high yield is obtained, and has the advantages of being quick in reaction and high in yield, and the good application value and the good market prospects are achieved.
- -
-
Paragraph 0046; 0047; 0048; 0049; 0050
(2016/12/26)
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- Construction of Benzimidazoles and Benzoxazoles through the Molybdenum-Mediated Carbonylation of Aryl Halides
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The facile and efficient one-pot construction of benzimidazoles and benzoxazoles through the Mo(CO)6-mediated carbonylation of aryl halides was examined. In the process, Mo(CO)6 acted as a convenient and safe solid source of carbon monoxide. A wide range of substrates were tolerated to provide the corresponding products in fair to good yields without the need of gaseous CO or palladium catalysts. The facile and efficient one-pot construction of benzimidazoles and benzoxazoles is described. The reaction proceeds through Mo(CO)6-mediated carbonylation of aryl halides, in which Mo(CO)6 acts as a convenient and safe solid source of carbon monoxide.
- Kebede, Eshetu,Tadikonda, Ramu,Nakka, Mangarao,Inkollu, Bhargavi,Vidavalur, Siddaiah
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supporting information
p. 5929 - 5933
(2015/09/22)
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- Synthesis of 2-substituted benzimidazoles using 25 % Co/Ce-ZrO2 as a heterogeneous and nanocatalyst
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25 % Co/Ce-ZrO2 nano fine particles are reported as a new catalyst for the efficient synthesis of 2-arylbenzimidazoles. A simple and convenient procedure, reusable catalyst, easy purification and shorter reaction times are the advantageous features of this method. Also prepared catalyst according to the coprecipitation method was characterized by common techniques such as SEM, XRD, FTIR and so on analysis. The catalyst is reusable and, reusable catalyst was characterized by XRD and FTIR techniques. Graphical Abstract: [Figure not available: see fulltext.]
- Behbahani, Farahnaz K.,Rezaee, Elham,Fakhroueian, Zahra
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p. 2184 - 2190
(2015/02/19)
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- Reusable α-MoO3 nanobelts catalyzes the green and heterogeneous condensation of 1,2-diamines with carbonyl compounds
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Crystalline nanobelts of α-MoO3 have been obtained successfully using novel and safe agents through a simple and safe sol-gel method (polymerizing-complexing) and characterized by XRD, FT-IR, Raman spectroscopies, high resolution transmission electron microscopy (HRTEM), scanning electron microscopy (SEM) and the temperature programmed desorption (TPD) of ammonia. An orthorhombic lattice system for nano-MoO3 was established. The HRTEM images showed that the nanobelt morphology of α-MoO3 mostly ranged from 20-70 nm in width and 200-400 nm in length. The ammonia TPD profile demonstrated strong acidic sites. The spectral and analysis data confirmed the effectiveness of the method for the preparation of α-MoO3 nanobelts by prevention of grain growth or agglomeration of the particles. The nanostructured MoO3 exhibited a high efficiency in catalyzing the condensation reaction of various 1,2-diamine and carbonyl compounds for synthesis of heterocyclic compounds. The recovery of the title heterogenous nanocatalyst was easy and efficient and its catalytic activity was strikingly different from the bulk material.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Ghahramaninezhad, Mahboube,Tabibi, Tooba
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p. 2087 - 2095
(2013/10/08)
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- DBSA mediated chemoselective synthesis of 2-substituted benzimidazoles in aqueous media
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An efficient synthetic method has been developed for the facile synthesis of 2-substituted benzimidazoles in organized aqueous media in the presence of a surfactant (viz. DBSA) as catalyst and I2 as co-catalyst. The method described has the advantages of operational simplicity, excellent yields, high chemoselectivity, and clean and green reaction profile.
- Kumar, Vikash,Khandare, Dipratn G.,Chatterjee, Amrita,Banerjee, Mainak
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p. 5505 - 5509
(2013/09/23)
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- Cu(I)-catalyzed synthesis of 2-substituted benzimidazoles from 2-iodoanilines and amides
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A novel and efficient approach to the synthesis of 2-substituted benzimidazoles has been developed via CuI/DMEDA-catalyzed coupling reaction and post-cyclization with glacial acetic acid from readily available 2-iodoanilines and amides. This method is suitable for the construction of a variety of benzimidazoles in moderate to good yields under short reaction times. A novel and efficient approach to the synthesis of 2-substituted benzimidazoles has been developed via CuI/DMEDA-catalyzed coupling reaction and post-cyclization with glacial acetic acid from readily available 2-iodoanilines and amides. This method is suitable for the construction of a variety of benzimidazoles in moderate to good yields under short reaction times. Copyright
- Yuan, Hua,Chen, Yongxin,Song, Jinli,Chen, Chunxia,Chen, Baohua
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supporting information
p. 1247 - 1249
(2013/11/06)
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- Polystyrene-supported pyridinium chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for selective synthesis of benzimidazoles
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Polystyrene-supported pyridinium chloroaluminate ionic liquid was prepared from the reaction of a Merrifield resin with pyridine followed by reaction with aluminium chloride. This catalyst was used as a new chemoselective Lewis acid catalyst for the exclusive synthesis of 2-substituted benzimidazoles from the reaction of aldehydes with o-phenylenediamines. The catalyst was stable (as a benchtop catalyst) and could easily be recovered and reused without appreciable change in its efficiency.
- Boroujeni, Kaveh Parvanak,Zhianinasab, Ashkan,Jafarinasab, Mina
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p. 155 - 164
(2013/08/25)
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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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- Efficient one-pot synthesis of 2-substituted benzimidazoles from triacyloxyborane intermediates
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An efficient one-pot synthesis of 2-substituted benzim?idazoles via triacyloxyborane intermediates is reported. The mild protocol is efficient and tolerant of acid-labile functional groups. Georg Thieme Verlag Stuttgart - New York.
- Cui, Wenge,Kargbo, Robert B.,Sajjadi-Hashemi, Zohreh,Ahmed, Feryan,Gauuan, Jolicia F.
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experimental part
p. 247 - 250
(2012/02/15)
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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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- Efficient one-pot synthesis of benzimidazoles under solvent-free conditions
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A green, efficient method for the synthesis of various 2-aryl- benzimidazoles in the presence of hypervalent iodine as the oxidant at room temperature under solvent-free conditions is reported. The salient features of this method include mild conditions, short reaction times (3-5min), excellent yields, and simple procedure.
- Du, Li-Hua,Luo, Xi-Ping
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experimental part
p. 2880 - 2886
(2010/10/19)
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- Rapid and cheap synthesis of benzimidazoles via intermittent microwave promotion: A simple and potential industrial application of air as oxidant
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Using inexpensive KI as the catalyst in the presence of ambient air, benzimidazoles were synthesized from aromatic aldehydes and o-phenylenediamine with excellent yields via intermittent microwave irradiation without reflux equipment. The synthesis process was mild and only needed only a short reaction time (7-10min). As a simple example of the utilization of molecular oxygen under mild conditions, this method provides a novel way to synthesize benzimidazoles. The industrial synthesis of benzimidazoles may be realized by a cycle of microwave irradiation. Copyright
- Mao, Zhengzhou,Wang, Zhaoyang,Li, Jingning,Song, Xiumei,Luo, Yufen
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experimental part
p. 1963 - 1977
(2010/09/07)
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- H2O2/Fe(NO3)3-promoted synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
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A new, convenient synthesis of 2-substituted benzimidazoles and benzothiazoles is described. Short reaction time, easy and quick isolation of the products, environmentally friendly procedure, excellent chemoselectivity and excellent yields are main advantages of this procedure. Georg Thieme Verlag Stuttgart.
- Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Naali, Fardin
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experimental part
p. 569 - 572
(2009/06/25)
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- A simple and efficient procedure for the synthesis of benzimidazoles using trichloroisocyanuric acid (TCCA) as the oxidant
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(Chemical Equation Presented) A Direct one step synthesis of various benzimidazoles from 3,4-diaminotoluene and benzaldehydes is described using TCCA as the oxidant. The salient features of this method include simple procedure, mild condition, no waste pr
- Bigdeli, Mohammad A.,Dostmohammadi, Hamideh,Mahdavinia, Gholam Hossein,Nemati, Firouzeh
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p. 1203 - 1205
(2008/12/20)
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- A simple and efficient one-pot synthesis of 2-substituted benzimidazoles
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A simple and efficient procedure for the synthesis of substituted benzimidazoles through a one-pot condensation of o-phenylenediamines with aryl aldehydes in the presence of H2O2/HCl system in acetonitrile at room temperature is described. Short reaction time, large-scale synthesis, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure. Georg Thieme Verlag Stuttgart.
- Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Kavianinia, Iman
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p. 547 - 550
(2008/01/03)
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- A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant
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Various 2-arylbenzimidazoles were synthesized from phenylenediamines and aldehydes via a one-step process using hypervalent iodine as an oxidant. The salient features of this method include mild conditions, short reaction times (3-5 min), high yields, and simple procedure. Georg Thieme Verlag Stuttgart.
- Du, Li-Hua,Wang, Yan-Guang
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p. 675 - 678
(2007/12/27)
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- H2O2/HCI as a new and efficient system for synthesis of 2-substituted benzimidazoles
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The system, H2O2/HCI, oxidises carbon-nitrogen bonds for the synthesis of benzimidazoles from aldehydes and diamines in water at 100°C. Both aryl aldehydes bearing electron-donating and electron-withdrawing substituents afforded desired benzimidazoles in excellent yields. This procedure is also applicable to substituted o-phenylenediamines, which produced 2-phenylbenzimidazoles smoothly in excellent yields. The simplicity of the system, the use of water as the solvent, large-scale synthesis and easy work-up are main advantages of this procedure.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Kavianinia, Iman
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p. 783 - 784
(2007/10/03)
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- A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant
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Direct one-step synthesis of various benzimidazoles from phenylenediamines and aldehydes is described using air as the oxidant. The salient features of this method include a simple procedure, mild conditions, no coupling agents or commercial oxidants/additives used, no waste produced (only by-product being water), easy purification, and high generality.
- Lin, Songnian,Yang, Lihu
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p. 4315 - 4319
(2007/10/03)
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- Synthesis and activities of 5-substituted- -2-(p-substituted phenyl)-1-dialkylaminomethyl benzimidazole derivatives
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Nine 1,2,5-trisubstituted benzimidazole derivatives were prepared and their structure have been elucidated by IR, NMR spectral data and elemental analyses. Analgesic activity of the compounds prepared was investigated in mice by modified KOSTER test. Anti
- Uzunoglu,Tosun,Ozden,Yesilada,Berkem
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p. 619 - 623
(2007/10/03)
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- A convenient approach to the synthesis of quinoxalines from isoxazolones and 1,2-diaminobenzenes
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2-Aryl-6,7-(un)substituted-quinoxalines (3a-t) and 2-arylbenzimidazoles (4a-t) have been obtained by condensation of 3-aryl-5(4H)-isoxazolones (1a-e) and 4-(un)substituted-1,2-diaminobenzenes (2a-d) under neutral conditions.The mechanism of their formation is illustrated.
- Rao, M Hanmantha,Reddy, A Pandu Ranga,Veeranagaiah, V
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