- N-Mannich bases of benzimidazole as a potent antitubercular and antiprotozoal agents: Their synthesis and computational studies
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This article dealing with the microwave assisted synthesis of N-Mannich bases of pyridine clubbed with two different benzimidazole cores with their micromolar biological potency. All the synthesized compounds were evaluated for their in-vitro antibacteria
- Patel, Vatsal M.,Patel, Navin B.,Chan-Bacab, Manuel J.,Rivera, Gildardo
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- Pyrophosphate Prompted Aggregation-Induced Emission: Chemosensor Studies, Cell Imaging, Cytotoxicity, and Hydrolysis of the Phosphoester Bond with Alkaline Phosphatase
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Two benzimidazole-based zinc complexes [(Zn)2(L2)2Cl2(DMSO)2] (R1) and [Zn(L2)2(NO3)2(H2O)2] (R2) were synthesized and characterized with various spectrosco
- Raj, Pushap,Singh, Amanpreet,Singh, Ajnesh,Singh, Ashutosh,Garg, Neha,Kaur, Navneet,Singh, Narinder
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- Syntheses, crystal structures, properties of metal coordination polymers based on a novel semi-rigid aromatic carboxylate ligand
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A set of new metal coordination polymers constructed from a novel semi-rigid aromatic carboxylate ligand, namely, [M(L)(4PBI)(H2O)]n(M?=?Ni, Co and Cu for 1, 2 and 3, respectively) and [Cd(L)(4PBI)]n(4) (H2L?=?3
- Wang, Cui-Cui,Tang, Gui-Mei,Wang, Yong-Tao,Wang, Jin-Hua,Cui, Yue-Zhi,Ng, Seik-Weng
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- Structural competition between hydrogen bonds and halogen bonds
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The molecules presented here provide a test-bed for competitive supramolecular chemistry, and on the basis of five crystal structures a ranking of the relative structural importance and influence of competing weak/strong hydrogen bonds and weak/strong hal
- Aakeroey, Christer B.,Fasulo, Meg,Schultheiss, Nate,Desper, John,Moore, Curtis
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- QUATERNARY SALTS OF QUINOLYLBENZIMIDAZOLES
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The nitrogen atoms of the benzimidazole ring are alkylated initially in the quaternization of 2-(2-quinolyl)benzimidazole, and the nitrogen atom of the quinoline ring is alkylated only after this.Pyridyl- and quinolylbenzimidazoles and their quaternary sa
- Romanenko, I. V.,Sheinkman, A. K.,Baranov, S. N.,Poltavets, V. N.,Klyuev, N. A.
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- A family of mixed-lanthanide metal-organic framework thermometers in a wide temperature range
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By choosing 2-pyridin-4-yl-4,5-imidazoledicarboxylic acid (H3PIDC) as the first ligand and sodium oxalate (OX) as the ancillary ligand, a series of mixed-lanthanide metal-organic frameworks (M′LnMOFs) [Tb1-xEux(HPIDC)(ox)1/2H2O]·3H2O (x = 0 1, 0.01 2a, 0.03 2b, 0.05 2c, 0.08 2d, 0.1 2e, 0.3 2f, 0.5 2g, 1 3) have been successfully synthesized via hydrothermal reactions. 2a-2f can serve as ratiometric luminescent sensors for detecting temperature. In this co-doped system, 2d shows an excellent linear response relationship with temperature from 303 to 473 K and exhibits a maximum relative sensitivity (Sr) of 0.60percent K-1 at 473 K. Furthermore, powder X-ray diffraction (PXRD) experiments indicate that 2d has excellent chemical stability under simulated physiological conditions and alkali-acid solutions with pH ranging from 4 to 11, which makes it suitable to be applied in the physiological environment.
- Feng, Yan,Huang, Haipeng,Liu, Weisheng,Qiu, Fangzhou,Song, Xuerui,Tang, Xiaoliang,Wang, Yingzhe,Yang, Yang,Zhang, Guolin
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- An advantageous synthesis of 2-substituted benzimidazoles using polyphosphoric acid. 2-(pyridyl)-1H-benzimidazoles, 1-alkyl-(1H-benzimidazol-2-yl)pyridinium salts, their homologues and vinylogues
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The title 2-substituted benzimidazoles are prepared by a highly efficient one-pot procedure, cyclodehydration of the corresponding accessible carboxylic acids and 1,2-arylenediamines, using polyphosphoric acid as the catalyst and solvent in a condensation of the type found in the Phillips benzimidazole synthesis. The method has been adapted and proved to be extremely useful for 1-alkyl-(1H-benzimidazol-2-yl)pyridinium tetrafluoroborates with a methylene and vinylene interannular moiety.
- Alcalde,Dinares,Perez-Garcia,Roca
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- A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles
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Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation of N-hydroxy intermediate, which at higher temperature cleaves to afford the desired product. This approach achieved reductions in reaction times, higher yields, cleaner reactions than the previously described synthetic processes.
- Kumar, Sonu,Sarmah, Manash P.,Reddy, Yella,Bhatt, Ashish,Kant, Ravi
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- Benzotrithiophene and triphenylamine based covalent organic frameworks as heterogeneous photocatalysts for benzimidazole synthesis
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Metal-free covalent organic frameworks (COFs) as visible-light active and recyclable photocatalysts afford an eco-friendly and sustainable option to classical photosensitizers, which usually require noble metals (iridium, ruthenium, rhodium, etc.) to produce photocatalytic activity. Most classical small molecule photosensitizers have poor recyclability with certain limitations. As a result, it is of great significance to develop a metal-free and easily recyclable COF photocatalyst. In this study, we designed and synthesized a new type of COF photocatalyst (BTT-TPA-COF) in which benzotrithiophene and triphenylamine units are alternately connected. It has high specific surface area, permanent porosity and good stability. In addition, this design strategy can effectively adjust the band gap, energy level and photoelectric performance of BTT-TPA-COF. As a metal-free photocatalyst, BTT-TPA-COF exhibits high-efficiency photocatalytic activity, excellent substrate tolerance and excellent recyclability for the synthesis of 2-arylbenzimidazole compounds. This research not only puts forward a design strategy for high-efficiency photocatalysts, but also broadens the application range of COF materials in photocatalytic organic reactions.
- Chen, Ying,Huo, Jianqiang,Luo, Bingcai,Zhang, Yubao
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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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- Cd-MOF@PVDF Mixed-Matrix Membrane with Good Catalytic Activity and Recyclability for the Production of Benzimidazole and Amino Acid Derivatives
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Mixed-matrix membranes (MMMs) incorporating metal-organic framework crystalline fillers as heterogeneous catalysts for organic transformation reactions have attracted more attention in catalysis science. Herein, a new 3D cadmium metal-organic framework (H3O)·[Cd(dppa)] (1) was first synthesized using the rigid 4-(3,5-dicarboxylphenyl)picolinic acid (H3dppa) as an organic ligand under solvothermal conditions, exhibiting a novel 6,6-connected network and good tolerance to various solvents. After activation, 1 showed good catalytic reactivity and selectivity for the synthesis of benzimidazole derivatives, affording solvent-dependent catalytic activity. Then, using the microcrystals of 1 and poly(vinylidene fluoride) (PVDF) as raw materials, 1@PVDF MMMs were successfully prepared by polymer solution casting. Notably, the integration of MOF and PVDF endows the mixed-matrix membrane 1@PVDF with great advantages in terms of more dispersive Lewis acid catalytic sites and recyclability. As expected, 1@PVDF not only displays good catalytic activity comparable to that of activated 1 but also exhibits remarkable recyclability and continuous usability for the production of benzimidazole and α-or β-amino acid derivatives. To the best of our knowledge, this is the first time that a Cd-based MOF and MMMs have been applied as a catalyst for the production of a β-amino acid. The combination of catalytic MOF and PVDF provides a way to simplify the design of a flow reactor and reduce the costs of manufacturing.
- Jiang, Yansong,Sun, Jing,Yang, Xiaona,Shen, Jieyu,Fu, Yu,Fan, Yong,Xu, Jianing,Wang, Li
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p. 2087 - 2096
(2021/02/06)
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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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- Benzimidazole compound with endothelial lipase inhibition effect and application of benzimidazole compound
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The invention discloses a benzimidazole compound with an endothelial lipase inhibition effect and application of the benzimidazole compound, and belongs to the technical field of medicines. The benzimidazole compound has an excellent inhibition effect on endothelial lipase, can effectively treating atherosclerosis and sequelae thereof, such as coronary heart disease, and also promotes treatment onmetabolic syndrome and sequelae thereof, such as diabetes. The benzimidazole compound provided by the invention has good solubility in an aqueous medium, also has good biological activity and metabolic stability, and shows advantages in the aspect of serum stability.
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Paragraph 0097-0103
(2020/12/09)
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- Development of 2-(4-pyridyl)-benzimidazoles as PKN2 chemical tools to probe cancer
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Kinases are signalling proteins which have proven to be successful targets for the treatment of a variety of diseases, predominantly in cancers. However, only a small proportion of kinases (50 of 0.064 μM against PKN2, with ca. 17-fold selectivity over close homologue, PKN1.
- Elkins, Jonathan M.,Fala, Angela M.,Massirer, Katlin B.,Pennicott, Lewis E.,Reuillon, Tristan D.,Scott, Fiona,Ward, Simon E.
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- Synthesis and biological evaluation of new N-benzylpyridinium-based benzoheterocycles as potential anti-Alzheimer's agents
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A novel series of benzylpyridinium-based benzoheterocycles (benzimidazole, benzoxazole or benzothiazole) were designed as potent acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The title compounds 4a-q were conveniently synthesiz
- Salehi, Naeimeh,Mirjalili, Bi Bi Fatemeh,Nadri, Hamid,Abdolahi, Zahra,Forootanfar, Hamid,Samzadeh-Kermani, Alireza,Kü?ükk?l?n?, Tuba Tüylü,Ayazgok, Beyza,Emami, Saeed,Haririan, Ismaeil,Sharifzadeh, Mohammad,Foroumadi, Alireza,Khoobi, Mehdi
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p. 559 - 568
(2018/11/26)
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- Synthesis of pyridinyl-benzo[d]imidazole/pyridinyl-benzo[d]thiazole derivatives and their yeast glucose uptake activity in vitro
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Background: Diabetes is the primary cause of fatality and disability all over the world, in recent past, we have reported various classes of compounds as anti-glycating agents and we have also reported benzimidazole and benzothiazole derivatives as a potential class of anti-glycating agents. This encouraged us to evaluate the pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 for yeast glucose uptake activity. Methods: In the present study, an equimolar mixture of pyridine carboxaldehyde derivatives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by addition of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice. Precipitates were formed which were collected by filtration to produce compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals. Results: Our present study showed that all compounds showed a varying degree of yeast glucose uptake activity in the range IC50 = 36.43-272.20 μM, compared to standard metronidazole (IC50 = 41.86 ± 0.09 μM). Compounds 5 (IC50 = 38.14 ± 0.17 μM), 6 (IC50 = 40.23 ± 0.20 μM), and 7 (IC50 = 36.43 ± 0.02 μM) showed an excellent yeast glucose uptake activity better than the standard. Conclusion: Pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 were synthesized, structurally characterized, and evaluated for in vitro yeast glucose uptake activity. Compounds 5 (IC50 = 38.14 ± 0.17 μM), 6 (IC50 = 40.23 ± 0.20 μM), and 7 (IC50 = 36.43 ± 0.02 μM) demonstrated potent yeast glucose uptake activity as compared to standard metronidazole (IC50 = 41.86 ± 0.09 μM). This study identified a number of potential lead molecules which can be helpful in lowering the blood glucose level in hyperglycemia.
- Khan, Momin,Ahmad, Riaz,Rehman, Gauhar,Gul, Naeem,Shah, Sana,Salar, Uzma,Perveen, Shahnaz,Khan, Khalid Mohammed
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p. 984 - 993
(2019/10/28)
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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 modern and practical laccase-catalysed route suitable for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
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Heterocyclic aromatic compounds containing an imine (C═N) bond such as benzimidazoles and benzothiazoles are important active pharmaceutical ingredients. The synthesis of 2-aryl-1H-benzimidazoles and 2-arylbenzothiazoles in good to excellent yields was ac
- Maphupha, Mudzuli,Juma, Wanyama P.,De Koning, Charles B.,Brady, Dean
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p. 39496 - 39510
(2018/12/13)
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- MIL-101(Fe) hexagonal microspindle as a highly efficient, reusable and versatile catalyst for benzo-fused heterocyclic nucleus synthesis
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A highly reusable, efficient and versatile MIL-101(Fe) catalyst was prepared and characterized using various techniques including Fourier transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy and energy-dispersive X-ray spectroscopy. This heterogeneous catalyst demonstrated a promising activity for condensation/cyclization reactions of various aryl aldehydes with 1,2-phenylenediamine or 2-aminothiophenol. The corresponding benzo-fused heterocyclic products were generated in good to excellent yields under mild conditions in the presence of the catalyst. In addition, the catalyst can be easily separated and reused in eight consecutive runs with consistent catalytic activity.
- Karimian, Ramin,Davarpanah, Seyed Javad
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- I2/TBHP promoted oxidative C–N bond formation at room temperature: Divergent access of 2-substituted benzimidazoles involving ring distortion
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A new ‘one pot’ tandem synthesis of 2-substituted benzimidazoles has been developed from 2-aminobenzyl alcohol/2-aminobenzamide and different coupling partners (nitriles, aldehydes and 1,3-diketones) via iodine and TBHP promoted oxidative ring contraction. The present strategy involves sequential C–N bond formation, cyclization, subsequent ring contraction and dehydrogenation to afford various medicinally important benzimidazole derivatives in moderate to good yields. This operationally simple synthetic approach proceeds at room temperature under base-free condition, broadly applicable to a wide array of nitriles and aldehydes bearing oxidation prone functional groups and noteworthy to mention that various acyclic 1,3-diketones undergo selective C–C bond cleavage leading to 2-alkyl benzimidazoles under mild condition.
- Saha, Moumita,Das, Asish R.
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supporting information
p. 2520 - 2525
(2018/05/31)
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- Chromium(III)-salen complex nanoparticles on AlPO4: as an efficient heterogeneous and reusable nanocatalyst for mild synthesis of highly functionalized piperidines, 2-arylbenzimidazoles, and 2-arylbenzothiazoles
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Abstract: A simple, convenient, and highly efficient multicomponent one-pot synthesis of highly functionalized piperidines has been developed via tandem reactions of β-keto esters, aromatic aldehydes, and various amines in ethanol at room temperature using catalytic amount (10?mol%) of a chromium(III)-salen complex nanoparticles supported on AlPO4. The heterogeneous catalyst exhibited excellent activity and reusability (up to 8 times) in the synthesis of highly functionalized piperidines. Also, synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles have been efficiently developed under mild condition from o-phenylenediamines or 2-aminothiophenol with aryl aldehydes via one-step process using catalytic amount (2.0?mol%) of nanocatalyst in air atmosphere as a green oxidant. The heterogeneous catalyst was characterized by scanning electron microscopy, atomic force microscopy, inductively coupled plasma spectrometry, thermogravimetry for analysis of nitrogen adsorption, and FT-IR spectroscopy. Graphical Abstract: [Figure not available: see fulltext.].
- Sharghi, Hashem,Aberi, Mahdi,Doroodmand, Mohammad Mahdi,Shiri, Pezhman
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p. 1557 - 1573
(2017/06/06)
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- Switch in Catalyst State: Single Bifunctional Bi-state Catalyst for Two Different Reactions
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Disclosed here is a molecular switch which responds to acid-base stimuli and serves as a bi-state catalyst for two different reactions. The two states of the switch serve as a highly active and poorly active catalyst for two catalytic reactions (namely a hydrogenation and a dehydrogenative coupling) but in a complementary manner. The system was used in an assisted tandem catalysis set-up involving dehydrogenative coupling of an amine and then hydrogenation of the resulting imine product by switching between the respective states of the catalyst.
- Semwal, Shrivats,Choudhury, Joyanta
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supporting information
p. 5556 - 5560
(2017/05/05)
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- N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C-H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes
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A novel class of N-doped cationic PAHs (polycyclic aromatic hydrocarbons) bearing the benzo[c,d]fluoranthene scaffold has been synthesized by the Rh(III)-catalyzed double-oxidative annulation of 2-arylbenzimidazoles with alkynes. The overall process involves a double C-N bond formation through a double C-H/N-H functionalization.The solid-state structures and electronic properties of the new N-doped PAHs were analyzed. These cationic azapolycycles were readily reduced in the presence of LiAlH4 or by the addition of PhLi to give interesting phenyl and diphenylmethanediamine derivatives.
- Villar, José M.,Suárez, Jaime,Varela, Jesús A.,Saá, Carlos
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supporting information
p. 1702 - 1705
(2017/04/11)
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- Phosphorous acid functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment for one-pot C-C and C-N bond formation reactions
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The preparation and application of fiber catalysts have attracted much attention. However, research on the effect of the micro-environment of fiber catalysts on the catalytic activities though of special importance is limited. In this work, a novel strategy for the synthesis of phosphoric acid-functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment by hydrophobic groups for one-pot C-C and C-N bond formation reactions is reported. The special hydrophobic surface micro-environment of the fiber catalysts is proven to promote the catalytic activities impressively in cyclocondensation of β-ketoesters with 2-aminobenzamides, the Knoevenagel condensation as well as the multi-component Biginelli reactions in green solvents. Both the surface synergy of the catalytic sites and hydrophobic auxiliary groups (benzyl or n-butyl) in the surface of fiber catalysts and interface acceleration in reaction medium play an important role in the highly efficient promotion of catalytic activity. Thereby a surface synergistic mechanism is proposed to explain the micro-environment effect. In addition, the fiber catalysts could be simply separated from the reaction system using tweezers and directly used in the next cycle without further treatment. Importantly, even after 10 reaction cycles in water or ethanol, there is no significant loss in their catalytic activity. The results indicate that the phosphoric acid functionalized fibers show green and sustainable potential for industrial production.
- Xu, Gang,Wang, Lu,Li, Mengmeng,Tao, Minli,Zhang, Wenqin
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supporting information
p. 5818 - 5830
(2017/12/26)
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- Structural and luminescent properties of a series of Cd(II) pyridyl benzimidazole complexes that exhibit extended three-dimensional hydrogen bonded networks
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Five new coordination complexes, [CdI2(3-PyBim)](H2O)3 (1), [Cd(SO4)(3-PyBim)(H2O)4] (2), [CdCl2(4-PyBim)2(H2O)2] (3), [CdBr2(4-PyBim)2(H2O)2] (4) and [CdI2(4-PyBim)2(H2O)2] (5) [3-PyBim=2-Pyridin-3-yl-1H-benzoimidazole, 4-PyBim=2-Pyridin-4-yl-1H-benzoimidazole], were obtained under hydrothermal conditions and characterized by single crystal X-ray diffraction, IR, elemental analysis, and powder X-ray diffraction. All of the complexes have mononuclear structures. Among the crystal structures of these complexes, there exist a variety of intermolecular hydrogen bonding interactions and π?π interactions, which further extend to a 3-D supramolecular architecture. The solid state photoluminescent properties of 1–5 vary with the electronegativity of the coordination anion. Additionally, the thermogravimetric analyses of these complexes are discussed.
- Wang, Jin-Hua,Tang, Gui-Mei,Qin, Ting-Xiao,Wang, Yong-Tao,Cui, Yue-Zhi,Ng, Seik?Weng
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p. 1168 - 1189
(2017/04/03)
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- Practical application of PhI(OAc)2/I2 combination to synthesize benzimidazoles from 2-aminobenzylamine through ring distortion strategy
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In this present work the combination of iodobenzenediacetate (PIDA)/iodine has been established as a promising reagent to promote the construction of 2-substituted benzimidazoles from 2-aminobenzylamine and a variety of easily available aldehydes/arylamines through a ring distortion strategy. The present protocol offers mild, metal free, robust conditions to synthesize 2-substituted benzimidazoles in good to excellent yields. In addition, the oxidation prone functional groups show tolerance during the reaction and after completion of the reaction pure products can be easily obtained applying hassle free filtration of the reaction mixture through silica gel bed.
- Saha, Moumita,Mukherjee, Prasun,Das, Asish R.
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p. 1046 - 1049
(2017/03/31)
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- Mild, one-pot preparation of 2-substituted benzimidazoles from organic halides
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Alkyl halides are feasibly transformed into benzimidazoles by a domino reaction under solvent-free conditions. The organic halides react with o-phenylenediamines in stoichiometric amounts in the presence of pyridine-N-oxide to produce the desired substituted benzimidazoles. This domino synthesis does not require catalysts. The synthesis occurs in dry medium and the environmental impact is minimal. The method provides products without intermediate separation. A mechanism of benzimidazole synthesis is also proposed.
- Br?tulescu, George
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supporting information
p. 811 - 817
(2017/04/06)
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- Isocyanurate-based periodic mesoporous organosilica (PMO-ICS): A highly efficient and recoverable nanocatalyst for the one-pot synthesis of substituted imidazoles and benzimidazoles
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Isocyanurate bridging periodic mesoporous organosilica (PMO-ICS) was shown to be a highly active and efficient recyclable catalyst for the three-component synthesis of imidazole derivatives from benzoin, different aldehydes and ammonium acetate under mild reaction conditions in short reaction times and good to excellent yields in EtOH. Also, benzimidazole derivatives were efficiently prepared from o-phenylenediamine and different aldehydes in the presence of PMO-ICS. Moreover, the catalyst was also recovered and reused at least four times without a significant decrease in its activity. The PMO-ICS catalyst was characterized by Fourier transformer infrared (FTIR) spectroscopy, thermogravimetry analysis (TGA), powder X-ray diffraction (XRD) and nitrogen adsorption-desorption isotherm (NADI) techniques as well as field emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM). Compared to the classical methodologies, this method illustrated significant advantages including low loading of the catalyst, avoiding the use of toxic transition metals or reactive reagents for modification of the catalytic activity, short reaction times, high to excellent yields, easy separation and purification of the products, and reusability of the catalyst.
- Dekamin, Mohammad G.,Arefi, Elham,Yaghoubi, Amene
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p. 86982 - 86988
(2016/10/19)
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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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- Synthesis of Schiff bases of pyridine-4-carbaldehyde and their antioxidant and DNA binding studies
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A series of Schiff bases of pyridine-4-carbaldehyde with 3-aminobenzoic acid, 2-aminobenzoic acid, 4-aminobenzoic acid, 1,3-phenylenediamine, 1,2-phenylenediamine, 2-aminothiophenol, 4-aminoantipyrene, 2-aminophenol and naphthalene-1-amine was synthesized
- Shamim, Saima,Murtaza, Shahzad,Nazar, Muhammad Faizan
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p. 494 - 503
(2016/08/31)
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- Copper(II)-Catalyzed Oxidative Cross-Coupling of Anilines, Primary Alkyl Amines, and Sodium Azide Using TBHP: A Route to 2-Substituted Benzimidazoles
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Copper(II)-catalyzed oxidative cross-coupling of anilines, primary alkyl amines, and sodium azide is described in the presence of TBHP at moderate temperature. This one-pot multicomponent protocol involves a domino C-H functionalization, transimination, ortho-selective amination, and a cyclization sequence. The broad substrate scope and functional group compatibility are the significant practical features. The protocol can be extended to the coupling of benzyl alcohols with moderate yields.
- Mahesh, Devulapally,Sadhu, Pradeep,Punniyamurthy, Tharmalingam
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p. 3227 - 3234
(2016/05/19)
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- B(C6F5)3 as versatile catalyst: An efficient and mild protocol for the one-pot synthesis of functionalized piperidines and 2-substituted benzimidazole derivatives
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An efficient, mild and environmentally benign protocol has been developed for the diastereoselective one-pot synthesis of functionalized piperidines via tandem reactions of aromatic aldehydes, amines and acetoacetic esters in the presence of a catalytic amount of tris(pentafluorophenyl)borane. Furthermore, B(C6F5)3 was successfully used to catalyze the synthesis of benzimidazole and its derivatives from various aldehydes and o-phenylenediamine. In addition, the applicability of the present protocol was extended for the synthesis of benzoxazoles and benzothiazoles.
- Prajapti, Santosh Kumar,Nagarsenkar, Atulya,Guggilapu, Sravanthi Devi,Babu, Bathini Nagendra
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p. 6795 - 6799
(2016/02/03)
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- Trichloroisocyanuric Acid/Triphenylphosphine-Mediated Synthesis of Benzimidazoles, Benzoxazoles, and Benzothiazoles
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A new and efficient method for preparation of benzimidazoles, benzoxazoles, and benzothiazoles from reactions of different carboxylic acids with o-phenylenediamine, o-aminophenol, and o-aminothiophenol in the presence of triphenylphosphine/trichloroisocyanuric acid system is presented. The desired products have been characterised on the basis of spectral (infrared, NMR, mass spectrometry) data, and the mechanism of their formation is proposed. The remarkable advantages are the inexpensive and readily available reagent, simple procedure, mild conditions, and good-to-excellent yields.
- Rezazadeh, Soodabeh,Akhlaghinia, Batool,Razavi, Nasrin
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p. 145 - 155
(2015/05/05)
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- Iron(II) bromide-catalyzed oxidative coupling of benzylamines with ortho-substituted anilines: Synthesis of 1,3-benzazoles
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An iron(II) bromide-catalyzed oxidative coupling of benzylamines with 2-amino/hydroxy/mercapto-anilines has been developed, allowing the synthesis of a diversity of substituted 1,3-benzazoles in good to excellent yields. This transformation is compatible with a wide range of functional groups. The method is practical, economical and employs molecular oxygen as an oxidant.
- Gopalaiah, Kovuru,Chandrudu, Sankala Naga
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p. 5015 - 5023
(2015/03/03)
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- Visible-light-promoted synthesis of benzimidazoles
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A simple and environmentally-friendly synthetic method for benzimidazoles, which are important structural motifs in many applications owing to their various biological functions, has been developed. The reaction of o-phenylenediamine and a variety of aliphatic/aromatic aldehydes in methanol proceeds at room temperature with only natural sources, molecular oxygen and visible light. A simple and eco-friendly synthetic method for benzimidazoles, which are important structural motifs in many applications owing to their various biological functions, has been developed. The reaction of o-phenylenediamine and a variety of aliphatic/aromatic aldehydes in methanol proceeds at room temperature with only natural sources, molecular oxygen and visible light. Copyright
- Park, Sehyun,Jung, Jaehun,Cho, Eun Jin
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p. 4148 - 4154
(2014/07/08)
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- Metal-free TEMPO-promoted C(sp3)-H amination to afford multisubstituted benzimidazoles
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An efficient TEMPO-air/cat. TEMPO-O2 oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp3 C-H and free N-H of readily available N1-benzyl/alkyl-1,2-phenylenediamines.
- Xue, Ding,Long, Ya-Qiu
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p. 4727 - 4734
(2014/06/09)
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- Design, synthesis, binding and docking-based 3D-QSAR studies of 2-pyridylbenzimidazoles - A new family of high affinity CB1 cannabinoid ligands
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A series of novel 2-pyridylbenzimidazole derivatives was rationally designed and synthesized based on our previous studies on benzimidazole 14, a CB1 agonist used as a template for optimization. In the present series, 21 compounds displayed high affinities with Ki values in the nanomolar range. JM-39 (compound 39) was the most active of the series (KiCB1 = 0.53 nM), while compounds 31 and 44 exhibited similar affinities to WIN 55212-2. CoMFA analysis was performed based on the biological data obtained and resulted in a statistically significant CoMFA model with high predictive value (q2 = 0.710, r2 = 0.998, r2pred = 0.823).
- Mella-Raipan, Jaime A.,Lagos, Carlos F.,Recabarren-Gajardo, Gonzalo,Espinosa-Bustos, Christian,Romero-Parra, Javier,Pessoa-Mahana, Hernan,Iturriaga-Vasquez, Patricio,Pessoa-Mahana, Carlos David
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p. 3972 - 4001
(2013/06/04)
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- Amberlyst-15-catalyzed synthesis of 2-substituted 1,3-benzazoles in water under ultrasound
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A clean and general method has been developed for the synthesis of benzothiazole, benzoxazole, and benzimidazoles using Amberlyst-15 as a recyclable catalyst under ultrasound irradiation in water. The methodology is operationally simple, free from the use of hazardous organic solvents, and does not require the use of inert or anhydrous atmosphere. A number of 1,3-benzazole derivatives were prepared in good to excellent yields by using this methodology.
- Rambabu,Murthi, P. Radha Krishna,Dulla, Balakrishna,Basaveswara Rao,Pal, Manojit
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supporting information
p. 3083 - 3092
(2013/09/12)
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- 2-heteroaryl benzimidazole derivatives as melanin concentrating hormone receptor 1 (MCH-R1) antagonists
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A novel series of 2-heteroaryl substituted benzimidazole derivatives, containing the piperidinylphenyl acetamide group at the 1-position, were synthesized and evaluated as MCH-R1 antagonists. Extensive SAR investigation probing the effects of C-2 heteroaryl group led to the identification of 2-[2-(pyridin-3-yl)ethyl] analog 3o, which exhibits highly potent MCH-R1 binding activity with an IC50 value of 1 nM. This substance 3o also has low hERG binding activity, good metabolic stability, and favorable pharmacokinetic properties.
- Lim, Chae Jo,Kim, Jeong Young,Lee, Byung Ho,Oh, Kwang-Seok,Yi, Kyu Yang
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p. 2305 - 2310
(2013/09/24)
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- γ-Maghemite-silica nanocomposite: A green catalyst for diverse aromatic N-heterocycles
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γ-Maghemite-silica nanocomposite has been applied as a green catalyst to synthesize variety of aromatic N-heterocycles under solvent free conditions. Characterization was done by modern analytical tools (UV, IR, AAS, DSC, EDXRF, powdered XRD, EPR, Mo?ssbauer and TEM). Mild reaction conditions and recyclability have made the present protocol both environmentally and economically viable.
- Ghosh, Pranab,Mandal, Amitava,Subba, Raju
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p. 146 - 152
(2013/09/02)
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- Benzimidazole derivatives: Synthesis, leishmanicidal effectiveness, and molecular docking studies
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Leishmanolysin GP63 is a zinc metalloprotease, expressed at the surface of Leishmania promastigotes. Studies on this protein are hindered as only a limited number of effective non-toxic inhibitors of this drug target are known. Present study describes the identification of a variety of 2-aryl- and 5-nitro-2-arylbenzimidazoles as new GP63 inhibitors. All the compounds were tested for in vitro activity against the promastigote form of Leishmania major and showed very good activity. 2-(Thiophen-2-yl)-1H-benzimidazole (19) and 2-(1H-indol-3-yl)-5-nitro-1H-benzimidazole (34) with IC50 value of 0.62 μg/mL were identified as lead of this library. Molecular docking studies were performed on binding site of GP63 to study the binding mode of compounds. The results of both in vitro and in silico studies clearly indicated that benzimidazoles may serve as new drug candidates in the combat against leishmaniasis.
- Shaukat, Awais,Mirza, Hira M.,Ansari, Amna H.,Yasinzai, Masoom,Zaidi, Sohail Z.,Dilshad, Sana,Ansari, Farzana L.
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p. 3606 - 3620
(2013/07/26)
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- Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles
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One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75-94%) was achieved within 60 min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy.
- Bommegowda, Yadaganahalli K.,Lingaraju, Gejjalagere S.,Thamas, Saji,Vinay Kumar, Koravangala S.,Pradeepa Kumara, Challanayakanahally S.,Rangappa, Kanchugarakoppal S.,Sadashiva, Marilinganadoddi P.
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supporting information
p. 2693 - 2695
(2013/06/05)
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- Iron sulfide catalyzed redox/condensation cascade reaction between 2-amino/hydroxy nitrobenzenes and activated methyl groups: A straightforward atom economical approach to 2-hetaryl-benzimidazoles and -benzoxazoles
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Iron sulfide generated in situ from elemental sulfur and iron was found to be highly efficient in catalyzing a redox/condensation cascade reaction between 2-amino/hydroxy nitrobenzenes and activated methyl groups. This method represents a straightforward and highly atom economical approach to 2-hetaryl-benzimidazoles and -benzoxazoles.
- Nguyen, Thanh Binh,Ermolenko, Ludmila,Al-Mourabit, Ali
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supporting information
p. 118 - 121
(2013/02/25)
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- Synthesis, in vitro and in silico NS5B polymerase inhibitory activity of benzimidazole derivatives
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Hepatitis C virus (HCV) NS5B polymerase is the key replicating protein of the virus and thus an attractive target for drug development. Here we report on the synthesis and biological evaluation of a new series of benzimidazole derivatives as HCV NS5B inhi
- Patil, Vaishali M.,Gurukumar,Chudayeu, Maksim,Gupta, Satya Prakash,Samanta, Subeer,Masand, Neeraj,Kaushik-Basu, Neerja
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experimental part
p. 629 - 635
(2012/10/08)
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- Efficient propylphosphonic anhydride (T3P) mediated synthesis of benzothiazoles, benzoxazoles and benzimidazoles
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Propylphosphonic anhydride (T3P) promotes cyclization of o-aminobenzenethiol, o-aminophenol, and o-phenylenediamine with carboxylic acids under microwave irradiation. The one-pot procedure is efficient and allows short reaction times, easy workup, and good yields. Thus, we describe here a method for quick preparation of benzothiazoles, benzoxazoles and benzimidazoles.
- Wen, Xiaoan,Bakali, Jamal El,Deprez-Poulain, Rebecca,Deprez, Benoit
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supporting information; experimental part
p. 2440 - 2443
(2012/06/01)
-
- Syntheses, characterizations, and antimicrobial activities of binuclear ruthenium(III) complexes containing 2-substituted benzimidazole derivatives
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Binuclear ruthenium(III) complexes [RuX3L]2· nH2O (X=Cl, L=L1, L2, L3; n=1, L4 and L5, X=Br; L=L3), [RuX3L 1.5]2·nH2O (X=Br, L=L1; n=0, L4; n=6 and L5; n=10), and [RuX3L 2]2 (X=Br, L=L2) have been isolated by treatment of hydrated RuX3 (X=Cl/Br) in acetone with 2-(2′-aminophenylbenzimidazole) (L1), 2-(3′- aminophenylbenzimidazole) (L2), 2-[(3′-N-salicylidinephenyl) benzimidazole] (L3), 2-(3′-pyridylbenzimidazole) (L 4), and 2-(4′-pyridylbenzimidazole) (L5) in acetone. The complexes were characterized by elemental analysis, conductivity and magnetic susceptibility measurements, IR, electronic, EPR, and mass spectral studies. The complexes were dimeric; based on analytical and spectral studies, an octahedral geometry was proposed for the complexes. The synthesized complexes were screened against Gram-positive and Gram-negative bacteria and fungi.
- Roopashree,Gayathri,Gopi,Devaraju
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p. 4023 - 4040
(2013/02/25)
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- IBX-mediated one-pot synthesis of benzimidazoles from primary alcohols and arylmethyl bromides
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A variety of primary alcohols are shown to be converted to the corresponding benzimidazoles in one pot by employing IBX and o-phenylenediamine in DMSO at room temperature. o-Iodobenzoic acid is the end product of IBX, which is employed in 1.0 equiv. Arylmethyl bromides are also shown to be converted likewise to benzimidazoles in moderate yields in one pot, albeit at slightly elevated temperatures.
- Moorthy, Jarugu Narasimha,Neogi, Ishita
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supporting information; experimental part
p. 3868 - 3871
(2011/08/06)
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- Syntheses, structures, and properties of transition metal complexes with 2-(n-pyridyl)benzimidazole (n=2, 3, and 4)
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Three pyridylbenzimidazoles (2-PBIM, 3-PBIM, and 4-PBIM) have been prepared (2-PBIM: 2-(2-pyridyl)-benzimidazole, 3-PBIM: 2-(3-pyridyl)-benzimidazole, 4-PBIM: 2-(4-pyridyl)-benzimidazole). Reactions of several transition metals (Cd2+, Cu2+, Fe2+) with the three ligands gave four new coordination complexes, [(Cd)2(2-PBIM)2(CH 3COO)4] (1), [Cu(3-PBIM)2 (CH 3COO)2] · 2H2O (2), [Cu(4-PBIM) 2(CH3COO)2(H2O)] · H 2O (3), and [Fe(4-PBIM)2 (Cl)2(H 2O)2] (4), respectively. These four complexes have been characterized by X-ray crystallography, IR spectroscopy, and UV absorption spectroscopy. Thermogravimetric properties of 2 and 4 were also measured. X-ray crystallographic studies reveal that these four complexes are very different, although the ligands are similar in structure. The role of hydrogen-bonding and π-π interactions in extending dimensionality of simple complexes has been discussed.
- Zhou, Ying-Xia,Li, Xia,Zhaang, Hai-Yan,Fan, Cai-Ling,Zhang, Hong-Yun,Wu, Ben-Lai
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experimental part
p. 4066 - 4078
(2012/03/11)
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- Two new silver(I) ammine complexes by displacement reaction between [Ag(NH3)2]+ ions and different pyridine-4,5-Imidazoledicarboxylic Acids
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[Ag(NH3)2]+ ions are chosen as an initial reaction precursor because of its simple displacement reaction and intrinsic arrangement as well as specific coordination directionality. Two new silver(I) ammine complexes, Ag2(NH3)HL2 (2) and Ag 2(NH3)2HL3 (3), were obtained by a simple substitution reaction between [Ag(NH3)2] + ions and pyridine-4,5-imidazoledicarboxylic acid [H 3L2 = 2-(3′-pyridyl) 4,5-imidazoledicarboxylic acid and H3L3 = 2-(4′-pyridyl) 4,5-imidazoledicarboxylic acid]. Silver dimers are connected into a 2D layer and 1D chain in complexes 2 and 3, respectively. In complex 2 two kinds of displacement reactions (mono-substituting and bis-substituting) occurred between the ammine molecules in [Ag(NH3)2]+ ions and H3L 2, however, only the mono-substituting reaction occurs in complex 3.
- Zhou, Rui-Sha,Song, Jiang-Feng,Li, Yan-Bin,Xu, Chun-Yan,Yang, Xiao-Feng
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experimental part
p. 251 - 256
(2011/04/26)
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- Anion-controlled assembly of silver(I) complexes of multiring heterocyclic ligands: A structural and photophysical study
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Four multiring heterocyclic ligands with benzimidazole (L1 and L3) and benzothiazole nuclei (L2 and L4) are reported. Their silver(I) complexes involving a variety of anions (both organic and inorganic) have been prepared by the process of self-assembly and structurally characterized by single-crystal X-ray diffraction analyses. Discrete metallocyclic complexes [Ag(L3)(X)]2 (X = NO 3-, 3a; cis-HOOCCH=CHCOO-, 3b; 0.5SiF6/2", 3c) and [Ag(L4)(Y)]2 (Y = NO3-, 4a; CF 3SO3-, 4b) have been formed with the ligands L3 and L4, respectively, where the pyridine nitrogen atom N1 is in the 3-position as against the coordination polymers [Ag(L1)H 2O)(NO3)]n, 1a, [Ag(L1)CF3COO)]n, 1b and {2[Ag(L2)2(C1O4)].0.5.C2H5OH}n 2a, and [Ag(L2)2(cis-HOOCCH=CHCOO)]n, 2b, with the ligands L1 and L2, respectively, in which the N1 atom occupies the 4-position in the pyridine ring. In addition to the primary ligands (L 1-L4), the counteranions also have a dominant influence on the overall structures of these compounds. Secondary bonding interactions, namely, hydrogen bonding, π...s- π-stacking, and C-H;...sn π interactions, are also proven effective in shaping the dimensionalities of the solid state structures. Thus, a zigzag chain structure of la mediated by a nitrate anion generates a more complicated double layer structure in 1b where trifluoroacetate has replaced nitrate as the counterion. Discrete 12-membered metallocycles in 3a-3c generate 2-D arrays of flat (3a) and undulating topologies (3b and 3c), depending upon the type of their associated anions. Metallocycles 4a and 4b have less complicated structures compared to those of 3a-3c because of the replacement of NH by S in the heterocyclic ring, thereby reducing the hydrogen-bonding potential in the primary ligand in going from L3 to L4. In the solid state, the complexes show enhanced phosphorescence at 77 K with triplet lifetime in the range of 0.5-0.8 s, much shorter than those for the free ligands (2.3 - 3.3 s) because of increased spin-orbit coupling introduced by the coordinated Ag+ ion. This heavy-atom effect also has a causative influence in shortening the fluorescence lifetimes of these compounds.
- Kundus, Nabanita,Audhya, Anandalok,Abtab, Sk Md Towsif,Ghosh, Sanjib,Tiekink, Edward R. T.,Chaudhury, Muktimoy
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experimental part
p. 1269 - 1282
(2011/12/02)
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- Discovery of dual inducible/neuronal nitric oxide synthase (iNOS/nNOS) inhibitor development candidate 4-((2-cyclobutyl-1 H-imidazo[4,5- b ]pyrazin-1-yl)methyl)-7,8-difluoroquinolin-2(1 H)-one (KD7332) Part 2: Identification of a novel, potent, and selective series of benzimidazole- quinolinone iNOS/nNOS dimerization inhibitors that are orally active in pain models
-
Three isoforms of nitric oxide synthase (NOS), dimeric enzymes that catalyze the formation of nitric oxide (NO) from arginine, have been identified. Inappropriate or excessive NO produced by iNOS and/or nNOS is associated with inflammatory and neuropathic pain. Previously, we described the identification of a series of amide-quinolinone iNOS dimerization inhibitors that although potent, suffered from high clearance and limited exposure in vivo. By conformationally restricting the amide of this progenitor series, we describe the identification of a novel series of benzimidazole-quinolinone dual iNOS/nNOS inhibitors with low clearance and sustained exposure in vivo. Compounds were triaged utilizing an LPS challenge assay coupled with mouse and rhesus pharmacokinetics and led to the identification of 4,7-imidazopyrazine 42 as the lead compound. 42 (KD7332) (J. Med. Chem. 2009, 52, 3047 -3062) was confirmed as an iNOS dimerization inhibitor and was efficacious in the mouse formalin model of nociception and Chung model of neuropathic pain, without showing tolerance after repeat dosing. Further 42 did not affect motor coordination up to doses of 1000 mg/kg, demonstrating a wide therapeutic margin.
- Payne, Joseph E.,Bonnefous, Céline,Symons, Kent T.,Nguyen, Phan M.,Sablad, Marciano,Rozenkrants, Natasha,Zhang, Yan,Wang, Li,Yazdani, Nahid,Shiau, Andrew K.,Noble, Stewart A.,Rix, Peter,Rao, Tadimeti S.,Hassig, Christian A.,Smith, Nicholas D.
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supporting information; experimental part
p. 7739 - 7755
(2011/02/22)
-
- CuI-catalyzed amination of arylhalides with guanidines or amidines: A facile synthesis of 1-H-2-substituted benzimidazoles
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(Figure Presented) CuI/L5 (N,N′-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-aminobenzimidazol
- Deng, Xiaohu,McAllister, Heather,Mani, Neelakandha S.
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supporting information; experimental part
p. 5742 - 5745
(2009/12/06)
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- 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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p. 415 - 418
(2008/09/20)
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