- Anti-inflammatory effect and inhibition of nitric oxide production by targeting COXs and iNOS enzymes with the 1,2-diphenylbenzimidazole pharmacophore
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Being the base of several non-communicable diseases, including cancer, inflammation is a complex process generated by tissue damage or change in the body homeostatic state. Currently, the therapeutic treatment for chronic inflammation related diseases is
- Gonzalez-Padilla, Jazmin E.,Castrejón-Flores, José L.,Franco-Hernández, Marina O.,Gómez-Castro, Carlos Z.,Gómez-Gómez, Yolanda M.,García-Aranda, Mónica I.,García-Báez, Efrén V.,Padilla-Martínez, Itzia I.,Rosales-Hernández, Martha C.
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Read Online
- s-Tetrazine-functionalized hyper-crosslinked polymers for efficient photocatalytic synthesis of benzimidazoles
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Developing green-safe, efficient and recyclable catalysts is crucial for the chemical industry. So far, organic photocatalysis has been proved to be an environmentally friendly and energy-efficient synthetic technology compared with traditional metal catalysis. As a versatile catalytic platform, hyper-crosslinked polymers (HCPs) with large surface area and high stability are easily prepared. In this report, we successfully constructed two porous HCP photocatalysts (TZ-HCPs) featurings-tetrazine units and surface areas larger than 700 m2g?1through Friedel-Crafts alkylation reactions. The rational energy-band structures and coexisting micro- and mesopores endow TZ-HCPs with excellent activities to realize the green synthesis of benzimidazoles (28 examples, up to 99% yield, 0.5-4.0 h) in ethanol. Furthermore, at least 21 iterative catalytic runs mediated by TZ-HCP1D were performed efficiently, with 96-99% yield. This study of TZ-HCPs sheds light on the wide-ranging prospects of application of HCPs as metal-free and green photocatalysts for the preparation of fine chemicals.
- An, Wan-Kai,Zheng, Shi-Jia,Zhang, Hui-Xing,Shang, Tian-Tian,Wang, He-Rui,Xu, Xiao-Jing,Jin, Qiu,Qin, Yuchen,Ren, Yunlai,Jiang, Song,Xu, Cui-Lian,Hou, Mao-Song,Pan, Zhenliang
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supporting information
p. 1292 - 1299
(2021/02/26)
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- Water extract of onion catalyst: An economical green route for the synthesis of 2-substituted and 1,2-disubstituted benzimidazole derivatives with high selectivity
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An efficient, environmental friendly and substrate controlled method of synthesis of 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 with high selectivity has been achieved from the reaction of o-phenylenediamine 1 and aldehydes 2 in the presence of water extract of onion and selecting suitable reaction medium. This method is widely applicable for variety of aldehydes such as aromatic/aliphatic/heterocyclic aldehydes and 1,2-diamines to afford 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 in good to excellent yields (up to 96%). The developed method of water extract of onion catalysis produced 2-substituted benzimidazoles 3 from aromatic aldehydes having electron-withdrawing groups, whereas aromatic aldehydes bearing electron donating groups selectively furnished 1,2-disubstituted benzimidazole 4 derivatives. The process described here has several advantages of cheap, low energy consumption, commercially available starting materials, operational simplicity and nontoxic catalyst. The use of water extract of onion makes this present methodology green and giving a useful contribution to the existing methods available for the preparation of benzimidazole derivatives. In addition, Hammett correlation of substituent constant (σ) vs percentage (%) yield has been established.
- Kaliyan, Prabakaran,Selvaraj, Loganathan,Muthu, Seenivasa Perumal
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supporting information
p. 340 - 349
(2020/12/01)
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- Tetrathienoanthracene-functionalized conjugated microporous polymers as an efficient, metal-free visible-light solid organocatalyst for heterogeneous photocatalysis
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Owing to their advantages of superior inherent porosity, high chemical stability, light weight, and molecularly tunable optoelectronic properties, conjugated microporous polymers (CMPs) have been receiving increasing attention and research interest as pro
- Chang, Jian-Guo,Han, Yin-Feng,Jiao, Guo-Zheng,Li, Qun,Li, Yan-Wei,Nie, Kun,Wang, Chang-An,Zhang, Jian-Ping
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p. 3799 - 3809
(2021/06/18)
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- Bandgap engineering in benzotrithiophene-based conjugated microporous polymers: a strategy for screening metal-free heterogeneous photocatalysts
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Metal-free conjugated microporous polymers (CMPs) as visible-light active and recyclable photocatalysts offer a green and sustainable alternative to classical metal-based photosensitizers. However, the strategy for screening CMP-based heterogeneous photocatalysts has not been interpreted up to now. Herein, we present a general strategy for obtaining excellent solid photocatalysts, which is to implement bandgap engineering in the same series of materials. As a proof of concept, three conjugated porous materials containing benzo[1,2-b:3,4-b′:5,6-b′′]trithiophene building blocks (BTT-CMP1, BTT-CMP2 and BTT-CMP3) were successfully constructed. They possess permanent porosity with a large specific surface area and excellent stability. By changing the linker between benzotrithiophene units, the bandgaps, energy levels and photoelectric performances including the absorption, transient photocurrent responses and photocatalytic performances of BTT-CMPs could be handily modulated. Indeed, BTT-CMP2 displayed the best catalytic activity for visible-light-induced synthesis of benzimidazoles among the three CMP materials, even higher than that of small molecule photocatalysts. As a metal-free photocatalyst, interestingly, the screened BTT-CMP2 also showed extensive substrate applicability and outstanding recyclability. Additionally, we have the opinion that this strategy will prove to be a guiding principle for screening superior CMP-based photocatalysts and broaden their application fields.
- Han, Songjie,Li, Ziping,Ma, Si,Zhi, Yongfeng,Xia, Hong,Chen, Xiong,Liu, Xiaoming
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supporting information
p. 3333 - 3340
(2021/02/26)
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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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- Photochemical Synthesis of Benzimidazoles from Diamines and Aldehydes
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An efficient, green, cheap, and metal-free photochemical protocol for the synthesis of benzimidazoles has been developed. 2,2-Dimethoxy-2-phenylacetophenone was employed as the photoinitiator and CFL lamps were used as the light source, leading to the cyc
- Skolia, Elpida,Apostolopoulou, Mary K.,Nikitas, Nikolaos F.,Kokotos, Christoforos G.
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supporting information
p. 422 - 428
(2020/12/13)
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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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- Synthesis of sulfonylated benzimidazo[2,1-a]isoquinolin-6(5H)-ones via I2O5-induced radical relay addition/cyclization of activated alkenes with sulfonylhydrazides
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A facile I2O5 induced radical relay addition/cyclization of activated alkenes with sulfonylhydrazides has been successfully developed, leading to a broad range of sulfonylated benzimidazo[2,1-a]isoquinolin-6(5H)-ones in moderate to good yields. The protocol has advantages of a metal-, base-, acid-, peroxide-free process, simple operation, and broad functional group tolerance.
- Tang, Yucai,Yang, Meng,Wang, Feifei,Hu, Xia,Wang, Gang
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supporting information
(2021/03/01)
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- Visible-Light-Induced Deaminative Alkylation/Cyclization of Alkyl Amines with N-Methacryloyl-2-phenylbenzoimidazoles in Continuous-Flow Organo-Photocatalysis
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Herein, we present a metal-free visible-light-induced eosin-y-catalyzed deaminative strategy for the sequential alkylation/cyclization of N-methacryloyl-2-phenylbenzoimidazoles with alkyl amine-derived Katritzky salts, which provides an efficient avenue for the construction of various benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives in moderate to excellent yields under mild reaction conditions. The key enabling feature of this novel reaction includes utilization of redox-active pyridinium salts from abundant and inexpensive primary amine feedstocks that were converted into alkyl radicals via C-N bond scission and subsequent alkylation/cyclization with N-methacryloyl-2-phenylbenzoimidazoles by the formation of two new C-C bonds. In addition, we implemented this protocol for a variety of amino acids, affording the products in moderate yields. Moreover, the novel, environmentally benign batch protocol was further carried out in a continuous-flow regime by utilizing a perfluoroalkoxy alkane tubing microreactor under optimized reaction conditions with a blue light-emitting diode light source, enabling excellent yields and a shorter reaction time (19 min) versus the long reaction time (16 h) of the batch reaction. The reaction displays excellent functional group tolerance, easy operation, scalability, mild reaction conditions, and broad synthetic utility.
- Ramesh, Vankudoth,Gangadhar, Maram,Nanubolu, Jagadeesh Babu,Adiyala, Praveen Reddy
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supporting information
p. 12908 - 12921
(2021/09/18)
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- Thiophene-embedded conjugated microporous polymers for photocatalysis
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Various photoactive building blocks can be incorporated into porous organic polymers (POPs). The intrinsic properties, such as various synthetic methods, outstanding inherent porosity, easy tunability, rigid conjugated skeletons and high stability, endow the polymeric organic networks with wonderful potential to act as heterogeneous photocatalytic platforms. However, exploitation of efficient synthetic strategies for metal-free and nontoxic heterogenous photocatalysts, and further insights into the photocatalytic process in organic transformations are still necessary. In this context, we report the concise synthesis of two polymeric frameworks (BTP-CMP and TBTP-CMP) incorporated into bithiophene and thiophthene units via a "bottom-up"strategy. BTP-CMP and TBTP-CMP were employed as heterogeneous photocatalysts in the synthesis of benzimidazoles, and exhibited excellent catalytic activity (up to 98% yield, at least 15 iterative runs). Therefore, the thiophene-embedded networks can serve as stable efficient and recyclable heterogeneous photocatalysts. Additionally, based on the catalytic results of control experiments and the energy band structures of the materials and intermediates, a possible photocatalytic reaction mechanism has been proposed.
- An, Wan-Kai,Cao, Zhan-Qi,Ding, San-Yuan,Du, Ya-Nan,Jiang, Song,Li, Zhi-Jun,Liu, Xiaobiao,Pan, Zhenliang,Qin, Yuchen,Song, Meirong,Wei, Pi-Feng,Zheng, Shi-Jia
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p. 5171 - 5180
(2020/09/07)
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- "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)
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- Solid Phase Synthesis of Biologically active Benzimidazole Derivatives Catalysed by CH3S03H-Si02 under Solvent free Condition
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A simple an expeditious method was established for the synthesis of 2-Substituted-1H-Benzimidazole derivatives at 90°C using o-phenylenediamine and different aldehydes. It has been found that a mixture of Methanesulphonic acid-Si02to be an effective catal
- Datta, Arup,Roy, Sanjay
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p. 537 - 543
(2020/07/23)
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- Vanadyl Acetylacetonate-Copper (II) Trifluoro Methane Sulfonate Catalyzed Eco-friendly Synthesis of Substituted Benzimidazoles in Aqueous Media
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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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- Development of benzimidazole-based derivatives as antimicrobial agents and their synergistic effect with colistin against gram-negative bacteria
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Gram-negative bacteria pose a distinctive risk worldwide, especially with the evolution of major resistance to carbapenems, fluoroquinolones and colistin. Therefore, development of new antibacterial agents to target Gram-negative infections is of utmost importance. Using phenotypic screening, we synthesized and tested thirty-one benzimidazole derivatives against E. coli JW55031 (TolC mutant strain). Compound 6c showed potent activity with MIC value of 2 μg/ml, however, it lacked activity against several Gram-negative microbes with intact efflux systems, including E. coli BW25113 (wild-type strain). Combination of 6c with colistin partially restored its antibacterial activity against wild strains (MIC range, 8–16 μg/ml against E. coli, K. pneumoniae, A. baumannii, and P. aeruginosa). 6c exhibited no cytotoxicity against two mammalian cell lines. Therefore, compound 6c represents a promising lead for further optimization to overcome Gram-negative resistance alone or in combination therapy.
- Dokla, Eman M.E.,Abutaleb, Nader S.,Milik, Sandra N.,Li, Daoyi,El-Baz, Karim,Shalaby, Menna-Allah W.,Al-Karaki, Rawan,Nasr, Maha,Klein, Christian D.,Abouzid, Khaled A.M.,Seleem, Mohamed N.
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- Oxidative Radical Relay Functionalization for the Synthesis of Benzimidazo[2,1-a]iso-quinolin-6(5H)-ones
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Here, a mild and general oxidative radical relay carbocyclization reaction with 2-arylbenzoimidazoles and cyclic ethers is reported. This method provides an efficient access to a wide range of structurally diverse benzimidazo[2,1-a]isoquinoline-6(5H)-ones under metal-free conditions. The wide substrate scope, good functional group tolerance, and scale-up operation of this method are expected to promote its potential applications in biotechnology and pharmacy. (Figure presented.).
- Sun, Kai,Li, Guofeng,Li, Yuyang,Yu, Jie,Zhao, Qing,Zhang, Zhiguo,Zhang, Guisheng
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p. 1947 - 1954
(2020/03/23)
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- A Green, Scalable, One-Minute Synthesis of Benzimidazoles
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Herein is reported a substantially improved synthesis of 2-substituted benzimidazoles by condensation of 1,2-diaminoarenes and aldehydes using methanol as the reaction medium. The developed method afforded moderate to excellent yields (33-96percent) at am
- Elumalai, Vijayaragavan,Hansen, Jorn H.
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supporting information
p. 547 - 552
(2020/03/27)
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- New synthesis method of thiabendazole
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The invention relates to a new synthetic route of a drug commonly named as thiabendazole. Thiazole-4-formaldehyde is used as a raw material, and is condensed with hydroxylamine hydrochloride to obtainthiazole-4-formaldoxime, thiazole-4-formaldoxime is subjected to chlorination by using NCS, and then reacts with aniline to obtain N-phenylthiazole-4-methylamine oxime, then N-phenylthiazole-4-methylamine oxime reacts with p-trifluoromethyl benzoyl chloride to obtain an amidoxime ester, and finally a visible-light-catalyzed free radical reaction is adopted for cyclization to obtain thiazole. According to the method, the visible-light-catalyzed free radical reaction is used to the synthesis of thiabendazole for the first time, the reaction conditions of a high temperature and a strong acid inthe traditional synthesis method are avoided, and thereby the reaction is greener and milder. The method has a broad spectrum, and can also be used for synthesis of imidazole compounds Ia-Ial.
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Paragraph 0026; 0035; 0036; 0037; 0038; 0160; 0161
(2020/02/20)
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- 2-ARYLBENZIMIDAZOLES AS PPARGC1A ACTIVATORS FOR TREATING NEURODEGENERATIVE DISEASES
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A genus of compounds encompassed by formula (III) and their use is disclosed: Formula (III). The compounds activate Ppargc1a and, as a consequence, are useful for treating a variety of neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), Alzheimer's disease, Parkinson's disease, Huntington's disease, frontotemporal degeneration, dementia with Lewy bodies, motor neuron diseases, and a demyelinating disease.
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Paragraph 85; 90
(2020/03/02)
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- Formation of Amidinyl Radicals via Visible-Light-Promoted Reduction of N-Phenyl Amidoxime Esters and Application to the Synthesis of 2-Substituted Benzimidazoles
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We have developed a new method for the synthesis of 2-substituted benzimidazoles via amidinyl radicals generated by visible-light-promoted reduction of N-phenyl amidoxime esters in the presence of an iridium photocatalyst. This is the first report of the use of N-phenyl amidoxime esters as amidinyl radical precursors, and the first use of substituted benzene rings as amidinyl radical acceptors. This method widens the application range of substrates and overcomes the shortcomings of the traditional methods for the synthesis of 2-substituted benzimidazoles, which requires harsh reaction conditions, involves difficult-to-prepare substituted o-phenylenediamine substrates, and produces acidic waste.
- Li, Gang,He, Ru,Liu, Qiang,Wang, Ziwen,Liu, Yuxiu,Wang, Qingmin
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p. 8646 - 8660
(2019/07/08)
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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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- Metallovesicles as smart nanoreactors for green catalytic synthesis of benzimidazole derivatives in water
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Metallovesicles are an emerging class of soft nanomaterials where spherical bilayer membranes, resulting from self-aggregation of amphiphilic metal complexes, amalgamate the advantages of metal specific catalytic properties and small hydrophobic cavities
- Kaur, Navneet,Kaur, Simranpreet,Kaur, Gurpreet,Bhalla, Aman,Srinivasan, Sesha,Chaudhary, Ganga Ram
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p. 17306 - 17314
(2019/07/31)
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- Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon
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A one-pot direct synthesis of a wide range of biologically active benzimidazoles through coupling of phenylenediamines and aldehydes catalyzed by a highly recyclable nonnoble cobalt nanocomposite was developed. A broad set of benzimidazoles can be efficiently synthesized in high yields and with good functional-group tolerance under additive- and oxidant-free mild conditions. The catalyst can be easily recycled for successive uses, and the process permits gram-scale syntheses of benzimidazoles.
- Wang, Zhaozhan,Song, Tao,Yang, Yong
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supporting information
p. 319 - 324
(2019/02/12)
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- Ultrasound-assisted synthesis of UiO-66-NHSO3H via post-synthetic modification as a heterogeneous Br?nsted acid catalyst
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Efficient SO3H-functionalized metal organic framework, UiO-66-NH-SO3H, has been successfully prepared through a post-synthetic modification strategy of UiO-66-NH2 with Chlorosulfonic acid reagent. The UiO-66-NH2 has been synthesized by an ultrasound-assisted (US) method and compared with the conventional-heating method. The UiO-66-NH-SO3H was characterized by elemental analysis, SEM, PXRD and FT-IR to serve as an efficient heterogeneous catalyst for the benzimidazole formation and reductive amination reaction. Furthermore, the UiO-66-NH-SO3H catalyst exhibits good stability, general applicability and excellent recycling performance.
- Homaee, Mahsa,Hamadi, Hosein,Nobakht, Valiollah,Javaherian, Mohammad,Salahshournia, Behrang
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p. 152 - 161
(2019/04/03)
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- Iron(III)–salen complex on a polymer scaffold as heterogeneous catalyst for synthesis of benzimidazoles
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Benzimidazoles are important bioactive compounds with diverse applications in the medicinal, industrial, as well as agrochemical fields. In this study, an iron–salen complex on a polymer scaffold was synthesized and characterized, and its performance asse
- Balinge, Kamlesh Rudreshwar,Datir, Sagar Krushnarao,Khajone, Vijay Baburao,Bhansali, Karan Jivanlal,Khiratkar, Avinash Ganesh,Bhagat, Pundlik Rambhau
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p. 155 - 168
(2018/09/25)
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- Metal-Free Visible-Light Promoted Radical Cyclization to Access Perfluoroalkyl-Substituted Benzimidazo[2,1-a]isoquinolin-6(5H)-ones and Indolo[2,1-a]isoquinolin-6(5H)-ones
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A metal-free visible-light-induced cyclization procedure was developed for the rapid synthesis of perfluoroalkyl-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones and perfluoroalkyl-substituted indolo[2,1-a]isoquinolin-6(5H)-ones under mild reaction conditions. In this procedure, the formation of electron-donor-acceptor (EDA) complex is critical for the visible-light promoted process to avoid the utilization of external photocatalysts. (Figure presented.).
- Zeng, Fan-Lin,Sun, Kai,Chen, Xiao-Lan,Yuan, Xiao-Ya,He, Shuai-Qi,Liu, Yan,Peng, Yu-Yu,Qu, Ling-Bo,Lv, Qi-Yan,Yu, Bing
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supporting information
p. 5176 - 5181
(2019/11/11)
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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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- Microwave use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds method
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The invention discloses a microwave the use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds, in the aqueous phase under microwave conditions adding benzoic amidine compound under alkaline condition [...] into benzimidazole reaction, invention an environment-friendly, the operation is simple, cheap and safe, efficient process for preparing benzimidazole method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection; .
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Paragraph 0048
(2019/03/28)
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- Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions
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The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.
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Paragraph 0018; 0028
(2019/01/21)
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- Method for preparing benzimidazole and quinazoline compounds by adopting supported nickel catalyst (by machine translation)
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The invention discloses a method for synthesizing benzimidazole and quinazoline compounds by oxidative coupling and dehydrogenation of a nitrogen-doped hierarchical porous biomass-based carbon material supported catalyst and a preparation method. The method comprises the following steps: adding o-phenylenediamine compound, alcohol, supported catalyst, toluene and potassium tert-butoxide as a solvent, carrying out reaction under 50~150 °C conditions, carrying out reaction 4~24 hours, cooling to room temperature, filtering the reaction liquid, and obtaining a benzimidazole compound or quinazoline compound. The method adopts "one-pot method" preparation, the intermediate can be separated and purified, energy consumption can be reduced, and the efficiency. (by machine translation)
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Paragraph 0054-0056; 0057; 0059
(2019/07/16)
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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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- Br?nsted acidic reduced graphene oxide as a sustainable carbocatalyst: A selective method for the synthesis of C-2-substituted benzimidazole
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Br?nsted acidic reduced graphene acts as an efficient and sustainable carbocatalyst for the selective synthesis of C-2-substituted benzimidazoles under ambient conditions. A massive influx of sulphonic acid group on reduced graphene oxide surface gives graphene sulfonic acid (G-SO3H), which acts as a Br?nsted acidic catalyst for the synthesis of a series of benzimidazoles under mild conditions. The present methodology is a revamp of the benzimidazole synthesis with broad functional group tolerance in shorter time. G-SO3H provides an operationally simple, metal-free condition and is amenable to gram-scale production. Pyridine adsorption studies prove the catalytically responsible Br?nsted acidity of the catalyst. The catalyst is highly stable for several cycles without any loss of activity, which is evidenced by the FT-IR, PXRD and TEM characterization of the reused catalyst.
- Karthik, Murugan,Suresh, Palaniswamy
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p. 17931 - 17938
(2018/11/21)
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- 4,5-Imidazoledicarboxylic acid immobilized on Fe3O4 magnetic nanoparticles: Preparation, characterization, and application as a recyclable and efficient nanocatalyst in the sonochemical condensation reaction
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A green synthesis of benzimidazole derivatives using recyclable magnetic 4,5-imidazoledicarboxylic is described. The magnetic 4,5-imidazoledicarboxylic (Fe3O4@ImDCA) nanocatalyst was characterized completely by infrared spectroscopy
- Shah Hosseini, Mohadesseh,Ghafuri, Hossein,Esmaili Zand, Hamid Reza
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p. 850 - 855
(2018/03/21)
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- Synthesis and characterization of an amidoxime compound with benzimidazole moiety and ph sensing behavior under basic condition in methanol and dmso
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An amidoxime containing 2-phenyl-1H-benzimidazole derivative, 4-(1H-Benzoimidazol-2-yl)-N-hydroxy-benzamidine, was synthesized by conversion of nitrile group of previously synthesized 2-(4-cyanophenyl)-1H-benzimidazole by treatment with hydroxylamine unde
- Rahman, Mohammad Nahidur,Bhowmick, Rina Rani,Nurnabi, Mohammad,Molla, Ashraful Islam
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p. 4047 - 4050
(2018/10/26)
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- Fluorenofluorene derivative and organic light-emitting device prepared by same
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The invention provides a fluorenofluorene derivative and an organic light-emitting device prepared by the same and relates to the technical field of organic photoelectric materials. The fluorenofluorene derivative and the organic light-emitting device prepared by the same have the advantages that the fluorenofluorene derivative is prepared by connecting a substituted or unsubstituted condensed imidazole derivative to a fluorenofluorene host, the prepared fluorenofluorene derivative has certain electron transport ability, the composition of holes and electrons on a light-emitting layer is benefited, and the fluorenofluorene derivative is good in stability and luminous efficiency, simple to synthesize, easy in synthesizing operation, capable of being used in the organic light-emitting deviceto serve as the light-emitting layer doping material and capable of effectively solving the problems that the blue light-emitting material in the organic light-emitting device is low in luminous efficiency and short in service life; the organic light-emitting device is high in luminous efficiency and long in service life.
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Paragraph 0057; 0058; 0063
(2018/10/19)
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- One-pot, green approach synthesis of 2-aryl substituted benzimidazole derivatives catalyzed by water extract of papaya bark ash
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A simple, green, rapid and environmentally benign route has been developed for the synthesis of 2-substituted benzimidazoles by the reaction of substituted o-phenylenediamine with different substituted benzoyl chloride using water extract of papaya bark ash (WEPBA) as a green catalyst at room temperature. This method provides several added advantages of being completely green, economic, giving high yields and minimizing use of hazardous solvents. Further, the separated product does not required any kind of chromatographic purification.
- Kantharaju,Hiremath, Prashant B.
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p. 1634 - 1638
(2018/06/12)
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- Method for catalytically synthesizing benzimidazole compound by organic protonic acid under condition of no solvent
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The invention discloses a method for catalytically synthesizing a benzimidazole compound by organic protonic acid under the condition of no solvent. According to the method provided by the invention,high efficiency catalysis is carried out to rapidly prep
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Paragraph 0015; 0044
(2018/11/27)
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- In water–ultrasound-promoted synthesis of tetraketones and 2-substituted-1H-benzimidazoles catalyzed by BiOCl nanoparticles
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A highly efficient, green protocol has been developed for the synthesis of various structurally diverse 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 2-substituted-1H-benzimidazole derivatives. The reaction was performed in water under ultrasound irradiation, using BiOCl nanoparticles as a catalyst. The nanocatalyst was found to be reusable for seven subsequent reactions without much loss in activity. Simple methodology with short reaction times and mild reaction conditions with easy work-up procedure are the salient features of this method.
- Sapkal, Bharatkumar M.,Labhane, Prakash K.,Satam, Jitendra R.
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p. 4967 - 4979
(2017/07/22)
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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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- Synthesis and antinociceptive activities of some novel benzimidazole-piperidine derivatives
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In this study, a series of benzimidazole-piperidine derivatives were synthesized with the objective of developing potent antinociceptive agents. Some 2-(4-substituted-phenyl)-1-[2-(piperidin-1-yl)ethyl]-1H-benzimidazole derivatives were obtaine
- Demir ?zkay, ümide,Can, ?zgür Devrim,Turan, Nazli,Kaya ?avu?o?lu, Betül
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p. 672 - 684
(2017/11/20)
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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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- Pharmacological and Toxicological Screening of Novel Benzimidazole-Morpholine Derivatives as Dual-Acting Inhibitors
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The aim of this study was to investigate acetylcholinesterase (AChE), monoamine oxidase A (MAO-A), monoamine oxidase B (MAO-B), cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzyme inhibitory, and antimicrobial activities of a new series of 2-(4-s
- Can, Nafiz nc,Evik, Ulviye Acar,Sagl?k, Beg m Nurpelin,Zkay, Yusuf,Atl?, Zlem,Baysal, Merve,Zkay, mide Demir,Can, zg r Devrim
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- Direct Synthesis of Benzimidazoles by Dehydrogenative Coupling of Aromatic Diamines and Alcohols Catalyzed by Cobalt
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Herein, we present the base-metal-catalyzed dehydrogenative coupling of primary alcohols and aromatic diamines to selectively form functionalized 2-substituted benzimidazoles, liberating water and hydrogen gas as the sole byproducts. The reaction is catalyzed by pincer complexes of Earth-abundant cobalt under base-free conditions.
- Daw, Prosenjit,Ben-David, Yehoshoa,Milstein, David
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p. 7456 - 7460
(2017/11/10)
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- Oxidative Synthesis of Benzimidazoles, Quinoxalines, and Benzoxazoles from Primary Amines by ortho-Quinone Catalysis
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The bioinspired ortho-quinone catalysts have been applied to heterocycles synthesis. Without any metal cocatalysts, a sole ortho-quinone catalyst enables the oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant.
- Zhang, Ruipu,Qin, Yan,Zhang, Long,Luo, Sanzhong
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supporting information
p. 5629 - 5632
(2017/10/25)
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- 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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- 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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- 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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- Method for catalytically synthesizing benzimidazole compound in water phase under microwave radiation
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The invention discloses a method for catalytically synthesizing a benzimidazole compound in a water phase under microwave radiation. The method comprises the following steps: adding a catalytic amount of metal chloride, proline lithium and a substituted 2-halogenated aniline substrate, ammonia water, a benzaldehyde derivative, inorganic alkali and water into a reaction container; putting the reaction container into a microwave reaction instrument to react at certain temperature and under certain power; after certain time, decompressing and concentrating; purifying a product through a column chromatography to obtain the benzimidazole compound, wherein the metal chloride in the step is iron chloride, cobalt chloride, nickel chloride or copper chloride, the inorganic alkali in the step is sodium hydroxide, cesium carbonate, sodium carbonate, potassium hydroxide or potassium phosphate, and reaction temperature of the microwave reaction instrument is 20 DEG C to 200 DEG C. The method for preparing the benzimidazole compound, provided by the invention, is environmental-friendly, is simple and convenient to operate, is safe and cheap and is efficient. Compared with the prior art, the method has the advantages of moderate reaction conditions, simplicity in operation, high yield, safety, low cost and environmental friendliness.
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Paragraph 0033; 0046
(2017/07/19)
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