- Visible-Light-Driven Sulfonylation/Cyclization to Access Sulfonylated Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-ones
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Visible-light-driven sulfonylation/cyclization of N-methacryloyl-2-phenylbenzoimidazoles has been successfully developed. Using commercially available sulfonyl chloride as sulfonylation reagent, a wide range of sulfonylated benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-ones with potential antitumor activity were provided in acceptable to excellent yields. This method has the advantages of mild reaction conditions and outstanding functional group tolerance, and provides a new strategy for the development of potential antitumor lead compounds.
- Wang, Chen,Sun, Guoquan,Huang, Hong-Li,Liu, Jing,Tang, Hua,Li, Yinghua,Hu, Honggang,He, Shipeng,Gao, Fei
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- Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole-based hydrazones: A synergistic experimental-computational analysis
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Present study advocates the joint experimental and computational studies of two potent benzoimidazole-based hydrazones with chemical formula C23H18F2N4O (5a) and C25H22FN5O3
- Rafiq, Muhammad,Khalid, Muhammad,Tahir, Muhammad Nawaz,Ahmad, Muhammad Umair,Khan, Muhammad Usman,Naseer, Muhammad Moazzam,Braga, Ataualpa Albert Carmo,Muhammad, Shabbir,Shafiq, Zahid
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- Method for catalytically synthesizing phenylbenzimidazole compound by using copper complex
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The invention relates to a method for catalytically synthesizing a phenylbenzimidazole compound by using a copper complex, which comprises the following steps: in the presence of alkali, taking benzimidazole and halogenated hydrocarbon as raw materials, taking the copper complex containing meta-carborane ligand as a catalyst, and conducting reacting at room temperature to prepare the phenylbenzimidazole compound. Compared with the prior art, the method has the advantages that the halogenated hydrocarbon compound which is low in cost and easy to obtain is used as the substrate, the reaction of benzimidazole and halogenated hydrocarbon is efficiently catalyzed by using the copper complex, the phenylbenzimidazole compound is synthesized by a one-pot method, the reaction condition is mild, the universality is good, the catalytic efficiency is high, few byproducts are produced, the cost is relatively low, the product is easy to separate, and lots of waste residues cannot be generated.
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Paragraph 0039-0042
(2021/08/06)
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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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- 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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- 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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- Nickel-Catalyzed C-F/N-H Annulation of 2-(2-Fluoroaryl) N-Heteroaromatic Compounds with Alkynes: Activation of C-F Bonds
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The reaction of 2-(2-fluoroaryl) N-heteroaromatic compounds, such as benzimidazole and indole derivatives, with internal alkynes in the presence of a catalytic amount of a nickel complex results in C-F/N-H annulation with alkynes. The reaction shows a high functional group compatibility. The presence of a strong base, such as KOBu- tor LiOBu t, is required for the reaction to proceed.
- Kawakami, Haruka,Nohira, Itsuki,Chatani, Naoto
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p. 3075 - 3080
(2021/02/03)
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- A one-pot synthesis of benzimidazoles via aerobic oxidative condensation of benzyl alcohols with o-phenylenediamines catalyzed by [MIMPs]+Cl-/NaNO2/TEMPO
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The ionic liquid 1-methyl-3-(3-sulfopropyl)imidazolium chloride ([MIMPs]+Cl-) in combination with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and sodium nitrite (NaNO2) as a catalytic system demonstrates high efficiency in the one-pot two-step aerobic oxidative condensation of benzyl alcohols with 1,2-phenylenediamines to give benzimidazoles. Various benzimidazoles are obtained in good to excellent yields by this strategy.
- Geng, Zhenzhen,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan
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p. 557 - 565
(2020/03/30)
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- Direct synthesis of 2-substituted benzimidazoles: Via dehydrogenative coupling of aromatic-diamine and primary alcohol catalyzed by a Co complex
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A Co(ii) complex with a stable structure was designed and synthesized with quinalic acid and Co (OAc)2·4H2O. The single crystal structure of the complex was characterized by X-ray diffraction. A dehydrogenative coupling of aromatic diamines and primary alcohols was developed by using the Co(ii) complex as the catalyst to synthesize 2-substituted benzimidazole. A series of 2-substituted benzimidazoles were obtained with good to excellent yields under mild reaction conditions. In addition, a compound with inhibitory Parkinson's activity was synthesized on a gram-scale by using this method. Finally, the reaction mechanism was proposed and the energy changes in the reaction process were simulated by density functional theory (DFT).
- Zuo, Minghui,Guo, Weihao,Pang, Yucheng,Guo, Rui,Hou, Chuanfu,Sun, Shouneng,Wu, Hongfeng,Sun, Zhizhong,Chu, Wenyi
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p. 14490 - 14495
(2020/10/03)
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- Nickel catalysed construction of benzazoles: Via hydrogen atom transfer reactions
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Herein we report a homogeneous, phosphine free, inexpensive nickel catalyst that forms a wide variety of benzazoles from alcohol and diamines by a reaction sequence of alcohol oxidation, imine formation, ring cyclization and dehydrogenative aromatization. A reversible azo/hydrazo couple, that is part of the ligand architecture steers both the alcohol oxidation and dehydrogenation of the annulated amine under fairly mild reaction conditions. Interestingly, both the alcohol oxidation and amine dehydrogenation steps are directly mediated by hydrogen atom transfer (HAT), which is greatly facilitated by the reduced ligand backbone. The kH/kD for the amine dehydrogenation step, measured at 60 °C is 5.9, fully consistent with HAT as the rate determining factor during this step. This is a unique scenario where two consecutive oxidation steps towards benzazole formation undergo HAT, which has been substantiated via kinetic studies, KIE determination and intermediate isolation. This journal is
- Adhikari, Debashis,Bains, Amreen K.,Dey, Dhananjay,Kundu, Abhishek,Yadav, Sudha
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p. 6495 - 6500
(2020/11/13)
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- 2-ARYLBENZIMIDAZOLES AS PPARGC1A ACTIVATORS FOR TREATING NEURODEGENERATIVE DISEASES
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A genus of compounds encompassed by formula (III) and their use is disclosed: Formula (III). The compounds activate Ppargc1a and, as a consequence, are useful for treating a variety of neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), Alzheimer's disease, Parkinson's disease, Huntington's disease, frontotemporal degeneration, dementia with Lewy bodies, motor neuron diseases, and a demyelinating disease.
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Paragraph 85; 90
(2020/03/02)
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- Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands
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Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.
- Mishra, Nidhi,Singh, Anoop S.,Agrahari, Anand K.,Singh, Sumit K.,Singh, Mala,Tiwari, Vinod K.
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supporting information
p. 389 - 399
(2019/05/06)
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- Visible-light-induced condensation cyclization to synthesize benzimidazoles using fluorescein as a photocatalyst
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A mild strategy for visible-light-induced synthesis of benzimidazoles was developed using aromatic aldehydes and o-phenylenediamines as substrates. The use of an organic dye, fluorescein, as an innoxious photocatalyst provided a mild and inexpensive catalytic system to synthesize a series of benzimidazoles in moderate to excellent yields. It was originally applied to this system to obtain benzimidazoles. Besides, the catalytic system does not require an additional oxidant or metal which was good for the environment.
- Li, Zhuofei,Song, He,Guo, Rui,Zuo, Minghui,Hou, Chuanfu,Sun, Shouneng,He, Xin,Sun, Zhizhong,Chu, Wenyi
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p. 3602 - 3605
(2019/07/09)
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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 0054
(2019/03/28)
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- Microwave-Assisted Nickel-Catalyzed Synthesis of Benzimidazoles: Ammonia as a Cheap and Nontoxic Nitrogen Source
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An efficient and convenient Ni-catalyzed C-N bond formation for the synthesis of various benzimidazoles from various 2-haloanilines, aldehydes, and ammonia in a concise manner is reported. This protocol uses commercially available, nonhazardous, clean ammonia as a reaction partner instead of other nitrogen sources. Benzimidazoles, as the sole products, were obtained in high to excellent yields (up to 95%).
- Ke, Fang,Zhang, Peng,Xu, Yiwen,Lin, Xiaoyan,Lin, Jin,Lin, Chen,Xu, Jianhua
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supporting information
p. 2722 - 2726
(2018/12/14)
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- Synthesis of benzimidazoles by Cul-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde in water
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An efficient copper-catalyzed three-component reaction of 2-haloaniline, ammonia and aldehyde for the synthesis of benzimidazoles with 1,10-phenanthroline as the ligand has been developed. A variety of substituted benzimidazole derivatives can be obtained in yields up to 95%.
- Ke, Fang,Zhang, Peng,Lin, Chen,Lin, Xiaoyan,Xu, Jianhua,Zhou, Xiangge
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supporting information
p. 8090 - 8094
(2018/11/23)
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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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- Sulfonic-acid-functionalized activated carbon made from tea leaves as green catalyst for synthesis of 2-substituted benzimidazole and benzothiazole
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Abstract: A simple and efficient procedure for synthesis of 2-substituted benzimidazole and benzothiazole has been developed by using sulfonic-acid-functionalized activated carbon as heterogeneous catalyst. The activated material was prepared from matured tea leaf in presence of phosphoric acid as activating agent. The final catalyst was prepared by anchoring –SO3H group on the surface of the activated carbon. The catalyst could be easily recovered and reused for more than three catalytic cycles without significant loss in catalytic activity. The catalytic performance of the catalyst was found to be superior to that of a similar catalyst prepared from montmorillonite K10. Graphical Abstract: [Figure not available: see fulltext.].
- Goswami, Mridusmita,Dutta, Mintu Maan,Phukan, Prodeep
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p. 1597 - 1615
(2017/11/17)
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- Iron(III) tetranitrophthalocyanine chloride immobilized on activated carbon: Efficient, excellent chemoselectivity and recyclable catalyst for synthesis of 2-substituted benzimidazoles
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The efficient and chemoselective preparation of 2-substituted benzimidazoles was established through the coupling of o-phenylenediamine with aldehydes by using iron(III) tetranitrophthalocyanine chloride immobilized on activated carbon as efficient catalyst in ethanol at room temperature. This method tolerated a variety of functional groups and had several advantages such as environmental friendliness, ease of manipulation, and a short reaction time. In addition, this catalyst can be recovered and reused for multiple cycles without loss in its catalytic activity.
- Qiu, Jun,Zhang, Yaodu,Hua, Chengwen,Gou, Xiaofeng,Chen, Bang,Zhao, Junlong
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p. 2153 - 2162
(2015/12/12)
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- Simple and efficient one-pot synthesis of 2-substituted benzimidazoles from θ-diaminoarene and aryl aldehydes
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An easy and efficient one-pot condensation method for the synthesis of substituted benzimidazoles from θ-phenylenediamines with aryl aldehydes using urea hydrogen peroxide (UHP) and I2 in dimethylsulfoxide (DMSO) provides wide substrate scope with good to excellent yields and simple and quick isolation of the products.
- Alapati, Mohan Lakshmi Punna Rao,Abburi, Sridhar Rao,Mukkamala, Saratchandra Babu,Krishnaji Rao
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supporting information
p. 2436 - 2443
(2015/11/10)
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- Microwave-assisted synthesis of substituted dibenzo[b,f][1,4]thiazepines, dibenzo[b,f][1,4]oxazepines, benzothiazoles, and benzimidazoles
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A highly efficient synthesis for possessing 7-membered rings with two heteroatoms is described, using efficient microwave-assisted one-pot method to synthesize (substituted) dibenzo[b,f][1,4]thiazepines [1] and dibenzo[b,f][1,4]oxazepines [2] in high yields (up to 99%) by cyclocondensations of o-aminothiophenol or o-aminophenol with o-halobenzaldehydes, o-fluoroacetophenone, and o-fluorobenzophenone. In the absence of base, o-aminothiophenol reacted with o-halobenzaldehydes to afford benzothiazoles.
- Lin, Yu-Chin,Li, Ni-Ching,Cherng, Yie-Jia
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p. 808 - 814
(2014/06/10)
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- Synthesis of benzimidazoles by copper-catalyzed aerobic oxidative domino reaction of 1,2-diaminoarenes and arylmethyl halides
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Arylmethyl halides are readily synthesized via halogenation from the basic raw materials, even in green processes. They are used to replace their downstream products to prepare medicinally important 2-aryl benzimidazoles. CuBr-catalyzed synthesis of 2-aryl benzimidazoles from arylmethyl halides and 1,2-diaminoarenes via a one-pot domino reaction is developed. This new synthetic method is simple, practical and cost saving, and tolerates wide functional groups. A mechanism of CuBr-catalyzed aerobic oxidative domino reaction via a one-pot four-step process is proposed.
- Qiu, Dezhi,Wei, Haidong,Zhou, Lihong,Zeng, Qingle
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p. 109 - 112
(2014/02/14)
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- Benzoyl methyl phosphates as efficient reagents in the one-pot tandem approach for the synthesis of 2-phenylbenzimidazoles in water
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A novel and efficient method for the environmentally benign, catalyst- and auxiliary-free synthesis of 2-phenylbenzimidazoles in water is developed. Benzoyl methyl phosphates play important roles as biomimetic acylating agents for the one-pot tandem approach without additional catalysts.
- Hikawa, Hidemasa,Imani, Maki,Suzuki, Hideharu,Yokoyama, Yuusaku,Azumaya, Isao
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p. 3768 - 3773
(2014/01/06)
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- Benzimidazoles: A new class of carbonic anhydrase inhibitors
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Carbonic anhydrase inhibitory activity of benzimidazole derivatives 1-24 has been evaluated. Compounds 22 (IC50 = 7.47 ± 0.39 μM), 21 (IC50 = 10.31 ± 0.11 μM), 20 (IC50 = 23.1 ± 1.78 μM), 12 (IC50 = 12.16 ± 0.10
- Khan, Khalid Mohammed,Khan, Momin,Saleem, Muhammad,Taha, Muhammad,Perveen, Shahnaz,Choudhary, Mohammad Iqbal
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p. 901 - 904
(2013/07/26)
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- A green synthesis of benzimidazoles
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Various 2-substituted benzimidazole derivatives in moderate to good yield have been prepared in a one-pot reaction by condensation of o-phenylenediamine and an aldehyde in the presence of ammonium chloride as a catalyst at 80-90°C. The reaction is green and economically viable.
- Kathirvelan,Yuvaraj,Babu,Nagarajan, Arasampattu S.,Reddy, Boreddy S.R.
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p. 1152 - 1156
(2013/09/24)
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- Combined Pd/C and montmorillonite catalysis for one-pot synthesis of benzimidazoles
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A series of nineteen benzimidazoles were prepared from ortho-nitroanilines by one-pot transfer hydrogenation, condensation, and dehydrogenation enabled by the concurrent use of two heterogeneous catalysts: montmorillonite-K10 and Pd/C. This strategy was further employed to accomplish a five-step, three-component synthesis of an antifungal benzimidazoquinazoline by using a simple one-pot procedure.
- Weires, Nicholas A.,Boster, Jared,Magolan, Jakob
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supporting information
p. 6508 - 6512
(2013/01/15)
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- Synthesis and β-glucuronidase inhibitory potential of benzimidazole derivatives
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Benzimidazole derivatives 1-24 have been synthesized and their in vitro β-glucuronidase inhibitory activitiy was evaluated. Compounds 15 (IC 50 = 6.33 ± 0.40 μM), 7 (IC50 = 22.0 ± 0.33 μM), 2 (IC50 = 23.1 ± 1.78 μM), 17 (I
- Khan, Khalid Mohammed,Khan, Momin,Ambreen, Nida,Rahim, Fazal,Naureen, Shagufta,Perveen, Shahnaz,Choudhary, M. Iqbal,Voelterc, Wolfgang
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body text
p. 421 - 427
(2012/09/05)
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- Citronellyl benzimidazoles
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Citronellyl benzimidazoles, e.g., (±) 1-(3,7-dimethyl-6-octen-1-yl)-2-phenylbenzimidazole, are prepared by reacting an alkali metal salt of a 2-phenylbenzimidazole with citronellyl halide and are useful as hypolipidemic agents.
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