- One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles
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It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.
- Guo, Tao,He, Jianghua,Liu, Tianwei,Zhang, Yuetao
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- Benzimidazole compound as well as preparation method and application thereof
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The invention provides a benzimidazole compound as well as a preparation method and application thereof. The structure of the benzimidazole compound is as shown in formula I in the specification. As a bipolar material, the benzimidazole compound provided
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Paragraph 0131-0135
(2021/06/22)
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- A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst
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This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is
- Vasu, Amrutham,Naresh, Mameda,Krishna Sai, Gajula,Divya Rohini, Yennamaneni,Murali, Boosa,Ramulamma, Madasu,Ramunaidu, Addipilli,Narender, Nama
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p. 9439 - 9446
(2021/12/09)
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- 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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- 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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- 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; 0198; 0199
(2020/02/20)
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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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- Method for generating nitrogen-containing heterocyclic ring products by catalyzing lignin and amino-containing compound with acid
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The invention provides a method for generating nitrogen-containing heterocyclic ring products by catalyzing lignin and an amino-containing compound with acid, belonging to the technical field of lignin degradation. According to the invention, lignin and the amino-containing compound are catalyzed by acid to directly generate the nitrogen heterocyclic derivatives in one step, and excellent yield (60-100%) is obtained in degradation of lignin; meanwhile, the method disclosed by the invention has high atom utilization rate; and in traditional degradation of lignin to generate benzaldehyde or benzoic acid, beta-C and gamma-C mostly generate byproducts such as formaldehyde, formic acid or carbon dioxide and cannot be fully utilized, but however, beta-C and gamma-C in lignin can generate nitrogen-containing heterocyclic ring products of the same series together with amino-containing compound raw materials according to the method in the invention, and the method has great application value inthe aspect of medicine.
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Paragraph 0129-0136
(2020/08/06)
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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; 0060
(2019/01/21)
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- Cobalt-Catalyzed Sustainable Synthesis of Benzimidazoles by Redox-Economical Coupling of o-Nitroanilines and Alcohols
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This study reveals cobalt-catalyzed sustainable synthesis of benzimidazoles by redox-economical coupling of o-nitroanilines and alcohols. The major advantage of this report is the use of a commercially available cheap cobalt catalyst to produce a wide variety of 2-substituted benzimidazoles by hydrogen autotransfer without using any additional external redox reagent and costly ligand system. A thorough mechanistic insight of the reaction is proposed by performing a series of control experiments.
- Das, Sanju,Mallick, Samrat,De Sarkar, Suman
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p. 12111 - 12119
(2019/10/02)
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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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- Virtual screening identification and chemical optimization of substituted 2-arylbenzimidazoles as new non-zinc-binding MMP-2 inhibitors
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Matrix metalloproteinases (MMPs) are a large family of zinc-dependent endoproteases known to exert multiple regulatory roles in tumor progression and invasiveness. This encouraged over the years the approach of MMP, and particularly MMP-2, targeting for anticancer treatment. Early generations of MMP inhibitors, based on aspecific zinc binding groups (ZBGs) assembled on (pseudo)peptide scaffolds, have been discontinued due to the clinical emergence of toxicity and further drawbacks, giving the way to inhibitors with alternative zinc-chelator moieties or not binding the catalytic zinc ion. In the present paper, we continue the search for new non-zinc binding MMP-2 inhibitors: exploiting previously identified compounds, a virtual screening (VS) campaign was carried out and led to the identification of a new class of ligands. The structure-activity relationship (SAR) of the benzimidazole scaffold was explored by synthesis of several analogues whose inhibition activity was tested with enzyme inhibition assays. By performing the molecular simplification approach, we disclosed different sets of single-digit micromolar inhibitors of MMP-2, with up to a ten-fold increase in inhibitory activity and ameliorated selectivity towards off-target MMP-8, compared to selected lead compound. Molecular dynamics calculations conducted on complexes of MMP-2 with docked privileged structures confirmed that analyzed inhibitors avoid targeting the zinc ion and dip inside the S1′ pocket. Present results provide a further enrichment of our insights for the design of novel MMP-2 selective inhibitors.
- Agamennone, Mariangela,Caradonna, Alessia,Di Pizio, Antonella,Laghezza, Antonio,Loiodice, Fulvio,Luisi, Grazia,Piemontese, Luca,Tortorella, Paolo
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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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- 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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- Biomass-Derived N-doped Carbon Materials with Silica-Supported Ultrasmall ZnO Nanoparticles: Robust Catalysts for the Green Synthesis of Benzimidazoles
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Ultrasmall ZnO nanoparticles anchored on N-doped carbon materials with a silica support (ZnO/SiO2-NC) were fabricated from chitosan and metal ions by using a one-pot self-assembly strategy and were successfully applied to the synthesis of 2-arylbenzimidazoles under mild conditions. These catalysts showed excellent stability and could be used six times without any loss of conversion and selectivity. The use of silica gel and the biomass chitosan as a source of hydrophilic N-doped carbon materials facilitated the uniform dispersion of the ZnO nanoparticles in methanol and therefore the contact of these nanoparticles with reactants, thus contributing to a high catalytic performance. TEM analysis showed that the ZnO nanoparticles were around 2.55 nm in diameter and uniformly distributed on the support surface. The binding behavior of ZnO and N-doped carbon materials affected the catalytic activity. Interestingly, temperature-programmed NH3 desorption indicated that the interactions between ZnO and N-doped carbon materials might induce the presence of more acidic sites in these catalysts, thus resulting in enhanced activity and hence promoting this transformation.
- Chen, Bo,Zhang, Chan,Niu, Libo,Shi, Xiaozhen,Zhang, Huiling,Lan, Xingwang,Bai, Guoyi
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p. 3481 - 3487
(2018/03/21)
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- Metal-free synthesis of N-containing heterocycles from O-substituted aniline derivatives via 2,4,6-trihydroxybenzoic acid-catalyzed oxidative dehydrogenation of benzylamines under oxygen atmosphere
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A series of N-heterocycles, i.e., benzimidazoles, benzoxazoles, and benzothiazoles, can be conveniently synthesized by the oxidative cyclization of benzylamines with o-substituted aniline derivatives, i.e., o-phenylenediamines, o-aminophenols, and o-aminothiophenols, using 2,4,6-trihydroxybenzoic acid as an organocatalyst under an oxygen atmosphere. This approach provides a mild and efficient tool towards benzimidazoles and benzothiazoles with good yields and a broad substrate scope. The developed synthesis of N-heterocycles might proceed via the oxidative dehydrogenation of benzylamines (ArCH2NH2), generating the corresponding imines (ArCH=NH) as key intermediates.
- Kumazawa, Shun,Uematsu, Akinori,Dong, Chun-Ping,Kodama, Shintaro,Nomoto, Akihiro,Ueshima, Michio,Ogawa, Akiya
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p. 842 - 853
(2019/04/26)
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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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- METHOD FOR THE SYNTHESIS OF BENZAZOLE
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PROBLEM TO BE SOLVED: To obtain a benzazole in a short reaction time with high yields. SOLUTION: A method for the synthesis of a benzazole includes a chemical reaction represented by the chemical reaction formula (1) to occur in subcritical water or supercritical water (X is NR6, O, or S. Y is H, OR7, halogen, or NR8R9. R1 to R9 are a C1-C20 aliphatic or aromatic substituent which may have O, N, S, B, Si, halogen, or P (two or more substituents of R1 to R6 may be coupled together, R8 and R9 may be coupled together, and two or more substituents of R1 to R9 may be the same) or H). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0036; 0041
(2017/09/19)
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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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- Denitrogenative Imidoyl Radical Cyclization: Synthesis of 2-Substituted Benzoimidazoles from 1-Azido-2-isocyanoarenes
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A novel access to 2-substituted benzoimidazoles, through unprecedented denitrogenative imidoyl radical cyclization of 1-azido-2-isocyanoarenes, has been developed. This tandem radical process was initiated by adding a C- or P-centered radical to isocyanide, followed by cycloaddition of the imidoyl radical to the azido group. Then, nitrogen loss and hydrogen abstraction of the resulting aminyl radical from surroundings delivered 2-substituted benzoimidazoles. Carbon radicals generated from another annulation process could also be applied, furnishing various heterocycle linked benzoimidazole derivatives.
- Li, Dengke,Mao, Tingting,Huang, Jinbo,Zhu, Qiang
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supporting information
p. 3223 - 3226
(2017/06/23)
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- Copper-Catalyzed Double C-N Bond Formation for the Synthesis of Diverse Benzimidazoles from N -Alkyl-2-iodoaniline and Sodium Azide
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An efficient approach to the synthesis of benzimidazole derivatives has been achieved by copper-catalyzed double C-N bonds formation of N-alkyl-2-iodoaniline and sodium azide. The reaction was supposed to proceed through copper-catalyzed tandem reaction of SNAr reaction, aerobic oxidation of C(sp3)-H bond and intramolecular C-N bond formation sequence. Structurally diverse 2-aryl, alkenyl and alkyl benzoimidazole derivatives were assembled by this methodology.
- Chen, Zhengkai,Li, Hongli,Cao, Gangjian,Xu, Jianfeng,Miao, Maozhong,Ren, Hongjun
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supporting information
p. 504 - 508
(2017/02/24)
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- Catalytic Oxidative Coupling of Primary Amines under Air: A Flexible Route to Benzimidazole Derivatives
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Benzimidazoles are of fundamental importance in chemistry and biology, and the development of efficient, environmentally benign methods for their preparation remains a key challenge for organic chemists. In a biomimetic approach inspired by copper amine oxidases, we disclose herein the scope and factors influencing the success of the cooperative action of CuBr2 as electron-transfer mediator and a topaquinone-like substrate-selective catalyst in the oxidative cyclocondensation of primary amines with o-aminoanilines. This one-pot atom-economic multistep process, which works under green conditions with ambient air as the terminal oxidant, low loadings of catalyst, and equimolar amounts of commercially available amine substrates, is particularly suitable for the preparation of 1,2-disubstituted benzimidazoles. Furthermore, it allows the functionalization of nonactivated primary aliphatic amines, which are known to be challenging substrates for non-enzymatic catalytic aerobic systems.
- Nguyen, Khac Minh Huy,Largeron, Martine
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p. 1025 - 1032
(2016/03/01)
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- Decarboxylative Coupling of α-Keto Acids with ortho-Phenylenediamines Promoted by an Electrochemical Method in Aqueous Media
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An electrochemical method for the decarboxylative coupling of α-keto acids with ortho-phenylenediamines was developed. The reaction proceeded smoothly in aqueous solution under air and metal catalyst-free conditions to afford 2-substituted benzimidazoles in good yields. Benzothiazoles could also be synthesized by this protocol. (Figure presented.) .
- Wang, Hai-Bin,Huang, Jing-Mei
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supporting information
p. 1975 - 1981
(2016/07/06)
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- Rapid production of benzazole derivatives by a high-pressure and high-temperature water microflow chemical process
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A high-pressure and high-temperature (HPHT) water microflow chemical process was utilized for the synthesis of benzazole derivatives. The current approach enables the extremely rapid production of various 2-arylbenzazoles including benzimidazoles, benzoxazoles, and benzthiazole in excellent yields.
- Nagao,Ishizaka,Kawanami
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supporting information
p. 3494 - 3498
(2016/07/06)
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- Electrochemical Synthesis of Benzazoles from Alcohols and o-Substituted Anilines with a Catalytic Amount of CoII Salt
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An electrochemical synthesis of benzazoles directly from alcohols and o-substituted anilines has been developed. The reaction conditions have been optimized by varying the composition of the electrolyte and the metal salt used as catalyst. The cyclization proceeds smoothly with a catalytic amount of a cobalt salt under air at room temperature to afford 2-substituted benzimidazoles, benzothiazoles, and benzoxazoles in good to excellent yields with a wide substrate scope.
- Lai, Yin-Long,Ye, Jian-Shan,Huang, Jing-Mei
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supporting information
p. 5425 - 5429
(2016/04/09)
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- An efficient route for the synthesis of benzimidazoles via a hydrogen-transfer strategy between o-nitroanilines and alcohols
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[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) has been used as an efficient catalyst for the synthesis of 2-substituted benzimidazoles via a hydrogen-transfer strategy. Various 2-substituted benzimidazoles were synthesized in good to excellent yields (up to 97%). The reaction shows good functional group tolerance. And no additional additive, oxidant, or reductant was required for the reaction.
- Li, Xiaotong,Hu, Renhe,Tong, Yao,Pan, Qiang,Miao, Dazhuang,Han, Shiqing
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supporting information
p. 4645 - 4649
(2016/09/23)
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- An electroluminescent compound and an electroluminescent device comprising the same
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The present invention relates to an organic light emitting compound applied to an organic light emitting device. The organic light emitting compound: is represented by chemical formula 1; includes one or more substituted bodies represented by structural formula 1 or structural formula 2; and is capable of realizing an organic light emitting device having excellent luminous properties such as driving voltage, luminance, a long life and the like in the case of being applied as a phosphorescent host compound in a hole transporting functional layer or an emissive layer.COPYRIGHT KIPO 2016
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Paragraph 0201; 0202; 0243; 0244
(2016/10/07)
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- Sodium sulfide: A sustainable solution for unbalanced redox condensation reaction between o -nitroanilines and alcohols catalyzed by an iron-sulfur system
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Unbalanced redox condensation reaction between o-nitroanilines and alcohols, leading to benzimidazole and quinoxaline heterocycles can be efficiently promoted and catalyzed by sodium sulfide (40 mol%) in combination with iron(III) chloride hexahydrate (1 mol%). Beside the role as a precursor for the iron-sulfur (Fe/S) catalyst formation, hydrated sodium sulfide was shown to be an excellent noncompetitive, multi-electron reducing agent.
- Nguyen, Thanh Binh,Ermolenko, Ludmila,Al-Mourabit, Ali
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p. 1741 - 1748
(2015/06/16)
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- An ammonium molybdate deposited amorphous silica coated iron oxide magnetic core-shell nanocomposite for the efficient synthesis of 2-benzimidazoles using hydrogen peroxide
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An ammonium molybdate deposited amorphous silica coated iron oxide (Fe 3O4@SiO2) magnetic core-shell nanocomposite was prepared and tested in the application to the synthesis of 2-benzimidazoles from aromatic aldehydes and o-phenylenediamines using hydrogen peroxide as an oxidant at room temperature. It was found that the yields were fundamentally influenced by the nature and position of the substituents on the phenyl ring. Brunauer-Emmett-Teller (BET) analysis, X-ray diffraction (XRD), transmission electron microscopy (TEM), energy-dispersive X-ray (EDX), and X-ray photoelectron spectroscopy (XPS) confirmed that the active ammonium molybdate species are highly dispersed on the surface of the Fe3O 4@SiO2 magnetic core-shell nanocomposite, accounting for its good activity. A method was eventually developed for the synthesis of 2-benzimidazoles highlighting the good activity and easily recyclable nature of this magnetic catalyst. This journal is the Partner Organisations 2014.
- Bai, Guoyi,Lan, Xingwang,Liu, Xiaofang,Liu, Chen,Shi, Lingjuan,Chen, Qingzhi,Chen, Guofeng
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p. 3160 - 3168
(2014/06/10)
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- Aerobic photooxidative synthesis of benzimidazoles from aromatic aldehydes and diamines using catalytic amounts of magnesium iodide
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This Letter proposes a safe, mild, and environmentally benign method for the synthesis of benzimidazoles from aromatic aldehydes and diamines by aerobic photooxidation using irradiation with visible light, a catalytic amount of magnesium iodide, which serves as both a Lewis acid and an oxidant, and molecular oxygen as the terminal oxidant.
- Nagasawa, Yoshitomo,Matsusaki, Yoko,Hotta, Toshiyuki,Nobuta, Tomoya,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
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p. 6543 - 6546
(2015/01/08)
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- Synthesis of benzimidazoles by potassium tert-butoxide-promoted intermolecular cyclization reaction of 2-iodoanilines with nitriles
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The synthesis of benzimidazoles by intermolecular cyclization reaction of 2-iodoanilines with nitriles has been developed. These reactions proceeded without the aid of any transition metals or ligands and just using KOBu t as the base. A variety of substituted benzimidazole derivatives can be synthesized by the approach.
- Xiang, Shi-Kai,Tan, Wen,Zhang, Dong-Xue,Tian, Xian-Li,Feng, Chun,Wang, Bi-Qin,Zhao, Ke-Qing,Hu, Ping,Yang, Hua
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supporting information
p. 7271 - 7275
(2013/10/22)
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- C-H cycloamination of N-aryl-2-aminopyridines and N-arylamidines catalyzed by an in situ generated hypervalent iodine(iii) reagent
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A metal-free synthesis of diversified pyrido[1,2-a]benzimidazoles and 1H-benzo[d]imidazoles from N-aryl-2-aminopyridines and N-arylamidines has been developed. The C-H cycloamination reaction was catalyzed by hypervalent iodine(iii) species generated in situ from iodobenzene (catalytic) and peracetic acid (stoichiometric). The reaction proceeded smoothly at ambient temperature to provide the corresponding N-heterocycles in good to excellent yields.
- He, Yimiao,Huang, Jinbo,Liang, Dongdong,Liu, Lanying,Zhu, Qiang
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p. 7352 - 7354
(2013/09/23)
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- Cobalt- and iron-catalyzed redox condensation of o-substituted nitrobenzenes with alkylamines: A step- and redox-economical synthesis of diazaheterocycles
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A wide variety of functionalized 2-aryl benzimidazoles can be prepared by a solvent-free cobalt- or iron-catalyzed redox condensation of 2-nitroanilines and benzylamines. The cascade including benzylamine oxidation, nitro reduction, condensation, and aromatization occurs without any added reducing or oxidizing agent. The method can be extended to other alkylamines as reducing components or 2-nitrobenzamides as oxidizing components when using an iron/sulfur catalyst to afford various diazaheterocycles.
- Nguyen, Thanh Binh,Bescont, Julie Le,Ermolenko, Ludmila,Al-Mourabit, Ali
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supporting information
p. 6218 - 6221
(2014/01/17)
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- Cu(I)-catalyzed synthesis of 2-substituted benzimidazoles from 2-iodoanilines and amides
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A novel and efficient approach to the synthesis of 2-substituted benzimidazoles has been developed via CuI/DMEDA-catalyzed coupling reaction and post-cyclization with glacial acetic acid from readily available 2-iodoanilines and amides. This method is suitable for the construction of a variety of benzimidazoles in moderate to good yields under short reaction times. A novel and efficient approach to the synthesis of 2-substituted benzimidazoles has been developed via CuI/DMEDA-catalyzed coupling reaction and post-cyclization with glacial acetic acid from readily available 2-iodoanilines and amides. This method is suitable for the construction of a variety of benzimidazoles in moderate to good yields under short reaction times. Copyright
- Yuan, Hua,Chen, Yongxin,Song, Jinli,Chen, Chunxia,Chen, Baohua
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supporting information
p. 1247 - 1249
(2013/11/06)
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- Selective autoxidation of benzylamines: Application to the synthesis of some nitrogen heterocycles
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A green and remarkably simple synthesis of nitrogen heterocycles from benzylamines and anilines o-substituted by a cyclizable group has been developed based on selective uncatalyzed autoxidation of benzylamines.
- Nguyen, Thanh Binh,Ermolenko, Ludmila,Al-Mourabit, Ali
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supporting information
p. 2713 - 2717
(2013/10/08)
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- CINNOLINE DERIVATIVES AS AS BTK INHIBITORS
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Disclosed are compounds of Formula 1, and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, and R5 are defined in the specification. The compounds are inhibitors of Bruton's tyrosine
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Paragraph 0489-0490
(2013/10/21)
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- Iron-catalyzed one-pot synthesis of benzimidazoles from 2-nitroanilines and benzylic alcohols
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The iron-catalyzed heterocyclizations from 2-nitroanilines and benzylic alcohols to form benzimidazoles using hydrogen transfer reaction were investigated in this study. In the presence of dppf in toluene at 150 °C, various benzimidazoles were obtained in moderate to good yields within 24 h. The reaction was proposed to proceed via a cascade of alcohol oxidation, nitro reduction, condensation, and dehydrogenation.
- Li, Gang,Wang, Jin,Yuan, Baokun,Zhang, Dongfeng,Lin, Ziyun,Li, Peng,Huang, Haihong
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supporting information
p. 6934 - 6936
(2019/04/10)
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- Aqueous synthesis of 1-H-2-substituted benzimidazoles via transition-metal-free intramolecular amination of aryl iodides
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A straightforward method has been developed for the synthesis of the benzimidazole ring system through a carbon-nitrogen cross-coupling reaction. In the presence of 2.0 equiv. of K2CO3 in water at 100 °C for 30 h, the intramolecular cyclization of N-(2-iodoaryl)benzamidine provides benzimidazole derivatives in moderate to high yields. Remarkably, the procedure occurs exclusively in water and doesn't require the use of any additional reagent/catalyst, rendering the methodology highly valuable from both environmental and economical points of view.
- Chen, Chunxia,Chen, Chen,Li, Bin,Tao, Jingwei,Peng, Jinsong
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p. 12506 - 12520
(2013/02/22)
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- Synthesis of benzimidazoles by PIDA-promoted direct C(sp2)-H imidation of N-arylamidines
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A metal-free synthesis of diversified benzimidazoles from N-arylamidines through a phenyliodine(III) diacetate (PIDA) promoted intramolecular direct C(sp2)-H imidation has been developed. The reaction proceeds smoothly at 0 °C or ambient temperature to provide the desired products in good to excellent yields. The synthesis of 2-alkyl- or 2-alkyl-fused benzimidazoles, which are generally inaccessible by similar Pd- or Cu-catalyzed approaches, can also be achieved. Copyright
- Huang, Jinbo,He, Yimiao,Wang, Yong,Zhu, Qiang
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supporting information
p. 13964 - 13967
(2013/01/15)
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- Indium-mediated one-pot benzimidazole synthesis from 2-nitroanilines or 1,2-dinitroarenes with orthoesters
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One-pot reduction-triggered heterocyclizations from 2-nitroanilines or 1,2-dinitroarenes to benzimidazoles were investigated in this study. In the presence of indium/AcOH in ethyl acetate at reflux, reaction of 2-nitroanilines or 1,2-dinitroarenes with R-C(OMe)3 (R=Me, Ph) produced excellent yields of the corresponding benzimidazoles within 30 min to 6 h depending on the substituents of the starting materials. Indium-mediated heterocyclization of 2-nitroanilines to benzimidazole was faster and had better yields than 1,2-dinitroarenes to benzimidazole under similar reaction conditions.
- Kim, Jaeho,Kim, Jihye,Lee, Hyunseung,Lee, Byung Min,Kim, Byeong Hyo
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experimental part
p. 8027 - 8033
(2011/11/06)
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- PROTEIN KINASE INHIBITORS
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Compounds that inhibit protein kinases, compositions containing the compounds and methods of treating diseases using the compounds are disclosed.
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Page/Page column 41
(2010/11/28)
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- A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant
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Direct one-step synthesis of various benzimidazoles from phenylenediamines and aldehydes is described using air as the oxidant. The salient features of this method include a simple procedure, mild conditions, no coupling agents or commercial oxidants/additives used, no waste produced (only by-product being water), easy purification, and high generality.
- Lin, Songnian,Yang, Lihu
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p. 4315 - 4319
(2007/10/03)
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- Syntheses of condensed imidazoles by lead tetraacetate oxidation of amidines
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2-Phenylbenzimidazoles, 2-benzylbenzimidazoles, 2-phenyl-1H-naphtholimidazole, and 2-benzyl-1H-naphtholimidazole have been synthesized in excellent yields (77-98percent) by lead tetraacetate oxidation of suitable N-arylbenzimides, N-arylphenylacetamidines, N-α-naphthylbenzimidine, and N-α-naphthylphenylacetamidine respectively.The mechanism of nitrene insertation and intramolecular competitive nitrene insertation leading to these heterocycles has also been discussed.
- Chaudhury, S.,Debroy, A.,Mahajan, M.P.
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p. 1122 - 1126
(2007/10/02)
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