- 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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supporting information
(2022/02/07)
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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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- H2 Activation with Co Nanoparticles Encapsulated in N-Doped Carbon Nanotubes for Green Synthesis of Benzimidazoles
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Co nanoparticles (NPs) encapsulated in N-doped carbon nanotubes (Co@NC900) are systematically investigated as a potential alternative to precious Pt-group catalysts for hydrogenative heterocyclization reactions. Co@NC900 can efficiently catalyze hydrogenative coupling of 2-nitroaniline to benzaldehyde for synthesis of 2-phenyl-1H-benzo[d]imidazole with >99 % yield at ambient temperature in one step. The robust Co@NC900 catalyst can be easily recovered by an external magnetic field after the reaction and readily recycled for at least six times without any evident decrease in activity. Kinetic experiments indicate that Co@NC900-promoted hydrogenation is the rate-determining step with a total apparent activation energy of 41±1 kJ mol?1. Theoretical investigations further reveal that Co@NC900 can activate both H2 and the nitro group of 2-nitroaniline. The observed energy barrier for H2 dissociation is only 2.70 eV in the rate-determining step, owing to the presence of confined Co NPs in Co@NC900. Potential industrial application of the earth-abundant and non-noble transition metal catalysts is also explored for green and efficient synthesis of heterocyclic compounds.
- Lin, Chuncheng,Wan, Weihao,Wei, Xueting,Chen, Jinzhu
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p. 709 - 720
(2020/11/30)
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- Preparation method of 2-substituted benzimidazole compound
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The invention discloses a preparation method of a 2-substituted benzimidazole compound, and belongs to the field of synthesis of benzimidazole compounds. The 2-substituted benzimidazole compound is synthesized in an organic solvent by taking an o-nitroaniline compound, aromatic aldehyde, o-dinitrobenzene and aromatic aldehyde as raw materials and taking Co particles wrapped by a nitrogen-doped carbon material as a catalyst. According to the method, the 2-substituted benzimidazole compound can be prepared at room temperature, the reaction conditions are mild, the yield is as high as 95%, the selectivity is as high as 99%, and the method is economical, environmentally friendly and wide in substrate applicability. The used catalyst is easy to prepare, low in cost and good in reusability, canbe separated by utilizing magnetism, and is convenient to recover, so that the method has a relatively strong industrial application prospect.
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Paragraph 0079-0083
(2021/02/20)
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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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- 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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- Benzimidazoles and benzothiazoles from styrenes and N-vinylimidazole via palladium catalysed oxidative C[dbnd]C and C[sbnd]N bond cleavage
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Herein we report a first, palladium catalyzed, one-pot methodology for the synthesis of pharmacologically important benzimidazoles and benzothiazoles from readily available terminal aromatic olefins. The process involves sequential C[dbnd]C/C[sbnd]N bond cleavage followed by C[sbnd]N/C[sbnd]S bond formation.
- Shaikh, Altab,Ravi, Owk,Pushpa Ragini,Sadhana, Nimma,Reddy Bathula, Surendar
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- Oxidative Cyclization Approach to Benzimidazole Libraries
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An efficient approach to the parallel synthesis of benzimidazoles from anilines is described. Library approaches to vary the N1 and C2 vectors of benzimidazoles are well established; however, C4-C7 variation has traditionally relied on 1,2-dianiline build
- Arnold, Eric P.,Mondal, Prolay K.,Schmitt, Daniel C.
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supporting information
p. 1 - 5
(2020/02/20)
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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; 0194; 0195
(2020/02/20)
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- Transforming Oxadiazolines through Nitrene Intermediates by Energy Transfer Catalysis: Access to Sulfoximines and Benzimidazoles
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Subtle differences in reaction conditions facilitated unprecedented photocatalytic reactions of oxadiazolines by energy transfer catalysis. A set of compounds, sulfoximines and benzimidazoles, were ingeniously prepared from oxadiazolines via nitrene intermediates by photocatalytic N-O/C-N bond cleavages. The synthesis of sulfoximines was realized through intermolecular N-S bond formation between nitrene intermediates and sulfoxides, whereas benzimidazoles were obtained via intramolecular aromatic substitution of the nitrene to the tethered aryl substituent.
- Park, Do Dam,Min, Kwan Hong,Kang, Jihee,Hwang, Ho Seong,Soni, Vineet Kumar,Cho, Cheon-Gyu,Cho, Eun Jin
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p. 1130 - 1134
(2020/02/15)
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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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- Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite under Mild Condition
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Regioselective ring nitration of N-alkyl anilines is reported using tert-butyl nitrite. The reactions proceed efficiently with a wide range of substrates providing synthetically useful N-nitroso N-alkyl nitroanilines in excellent yields which can be easily converted into N-alkyl phenylenediamines and N-alkyl nitroanilines using Zn-AcOH and HCl/MeOH, respectively.
- Chaudhary, Priyanka,Gupta, Surabhi,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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p. 104 - 119
(2019/01/08)
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- Iron-catalyzed one-pot sequential transformations: Synthesis of quinazolinones via oxidative Csp3–H bond activation using a new metal-organic framework as catalyst
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A new mixed-linker iron-based MOF VNU-21 [Fe3(BTC)(EDB)2·12.27H2O] was synthesized via mixed-linker synthetic strategy using 1,3,5-benzenetricarboxylic acid, 4,4′-ethynylenedibenzoic acid, and FeCl2. The VNU-21 was consequently used as a recyclable heterogeneous catalyst in the one-pot synthesis of quinazolinones via two steps under oxygen atmosphere. The synthetic scheme involved iron-catalyzed oxidative Csp3–H bond activation to achieve decarboxylation of phenylacetic acids, and succeeding metal-free oxidative cyclization with 2-aminobenzamides. The VNU-21 was more effective than a series of heterogeneous and homogeneous catalysts. It was possible to reutilize the iron-based framework without a considerable deterioration in catalytic performance. To our best knowledge, this one-pot synthesis of quinazolinones was not previously performed using a recyclable catalyst.
- To, Tuong A.,Vo, Yen H.,Nguyen, Hue T.T.,Ha, Phuong T.M.,Doan, Son H.,Doan, Tan L.H.,Li, Shuang,Le, Ha V.,Tu, Thach N.,Phan, Nam T.S.
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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.
- -
-
Paragraph 0018; 0058
(2019/01/21)
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- Metal-free selective synthesis of 2-substituted benzimidazoles catalyzed by Br?nsted acidic ionic liquid: Convenient access to one-pot synthesis of N-alkylated 1,2-disubstituted benzimidazoles
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A novel efficient method for the selective synthesis of 2-substituted benzimidazoles is described through condensation reaction of o-phenylenediamines with a wide rang of aliphatic, aromatic and heteroaromatic aldehyde substrates using Br?nsted acidic ionic liquid as a reusable catalyst under metal-free conditions at ambient temperature. Notably, Dodecylimidazolium hydrogen sulfate ([DodecIm][HSO4]) is the most efficient catalyst for good to excellent yields of the corresponding products (up to 98%). Subsequently, this protocol was successfully applied for the preparation of N-alkylated 1,2-disubstituted benzimidazoles in high to excellent yields via sequential one-pot reaction. In addition, catalysts are recycled at least four times without significant loss in activity.
- Senapak, Warapong,Saeeng, Rungnapha,Jaratjaroonphong, Jaray,Promarak, Vinich,Sirion, Uthaiwan
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p. 3543 - 3552
(2019/05/29)
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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; 0060
(2018/11/27)
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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 0067
(2017/07/19)
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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; 0044
(2017/09/19)
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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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- 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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- 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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- [Fe(F20TPP)Cl]-catalyzed amination with arylamines and {[Fe(F20TPP)(NAr)](PhI=NAr)}+. Intermediate assessed by high-resolution ESI-MS and DFT calculations
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Amination of C-H bonds catalyzed by transition metal complexes via nitrene/imide insertion is an appealing strategy for C-N bond formation, and the use of iminoiodinanes, or their in situ generated forms from 'PhI-(OAc)2 + primary amides (such as sulfonamides, sulfamates, and carbamates)', as nitrogen sources for the amination reaction has been well documented. In this work, a 'metal catalyst + PhI(OAc)2 + primary arylamines' amination protocol has been developed using [Fe(F20TPP)Cl] (H2F20TPP = meso-tetrakis(pentafluorophenyl)porphyrin) as a catalyst. This catalytic method is applicable for both intra- and intermolecular amination of sp2 and sp3 C-H bonds (> 27 examples), affording the amination products, including natural products such as rutaecarpine, in moderate-to-good yields. ESI-MS analysis and DFT calculations lend support for the involvement of {[Fe(F20TPP)(NC6H4-p-NO2)](PhI=NC6H4-p-NO2)}+. intermediate in the catalysis.
- Liu, Yungen,Chen, Guo-Qiang,Tse, Chun-Wai,Guan, Xianguo,Xu, Zheng-Jiang,Huang, Jie-Sheng,Che, Chi-Ming
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supporting information
p. 100 - 105
(2015/02/19)
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- Synthesis of benzimidazoles by Cu2O-catalyzed cascade reactions between o-haloaniline and amidine hydrochlorides
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An efficient Cu2O-catalyzed method for the synthesis of benzimidazole derivatives from amidine hydrochlorides and o-haloaniline has been developed. The cascade C-N coupling and intramolecular transamination reaction provided benzimidazole deriv
- Qu, Yanyang,Pan, Lei,Wu, Zhiqing,Zhou, Xiangge
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supporting information
p. 1717 - 1719
(2013/03/13)
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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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- 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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- Copper-catalyzed synthesis of benzazoles via aerobic oxidative condensation of o-amino/mercaptan/hydroxyanilines with benzylamines
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A simple and efficient method for the synthesis of benzazoles via Cu-catalyzed aerobic oxidative condensation of o-amino/mercaptan/hydroxyanilines with benzylamines was developed.
- Xiao, Tiebo,Xiong, Shengwei,Xie, Yang,Dong, Xichang,Zhou, Lei
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p. 15592 - 15595
(2013/09/12)
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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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- 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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- Assembly of substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2- ones via CuI/L-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates
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(Chemical Equation Presented) CuI/L-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates affords the aryl amination products at room temperature, which undergo in situ additive cyclization under acidic conditions or heating to give substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones, respectively. A wide range of functional groups including ketone, nitro, iodo, bromo, and ester are tolerated under these reaction conditions, providing these heterocycles with great diversity.
- Diao, Xiaoqiong,Wang, Yuji,Jiang, Yongwen,Ma, Dawei
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experimental part
p. 7974 - 7977
(2010/02/28)
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- Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides
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(Chemical Equation Presented) The identity of the ortho-substituent of an aryl azide influences its reactivity toward transition metals. Substitution of a vinyl group with an imine disables rhodium(II)-mediated C-H amination and triggers a Lewis acid mechanism catalyzed by iron(II) bromide to facilitate benzimidazole formation.
- Shen, Meihua,Driver, Tom G.
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supporting information; experimental part
p. 3367 - 3370
(2009/05/27)
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