cas 7035-68-9, N-Ethylbenzimidazole | Articles data

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Preparation and characterization of two bronsted acid ionic liquids
Two Bronsted acid task specific ionic liquids based on the benizimidazolium cation (1-ethylbenzimidazolium tetrafluoroborate {[H-eBim]BF4 (1)} and 1-propylbenzimidazolium tetrafluoroborate {[H-pBim]BF4 (2)}) were synthesized and characterized. The crystal of 1 is in orthorhombic system with space group Pnma, and the unit cell parameters as follows: a = 9.9308(16), b = 6.8813(11), c = 15.345(3) A, V = 1048.6(3) A3, Z = 4, Dc = 1.482 g/cm3. Structure 2 crystallizes in the monoclinic space group P21/c, with unit cell a = 4.9688(14), b = 13.684(4), c = 17.295(5) A, β = 92.090(6)°, V = 1175.2(6) A3, Z = 4, Dc = 1.402 g/cm3. These molecules are stabilized in solid state by various intra and intermolecular hydrogen bonding interactions to give polymeric structures.
Chen, Shuanhu,Wang, Mingtian,Wang, Fei,Yang, Fenrong,Shi, Suqing,Wang, Nani
p. 1027 - 1031
(2011)
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Incorporation of benzimidazolium ionic liquid in proton exchange membranes ABPBI-H3PO4
This paper presents the development of proton exchange membranes (PEM) from the incorporation of poly (2,5-benzimidazole) (ABPBI) in phosphoric acid (H3PO4) and ionic liquid (IL) 1-butyl-3- ethylbenzimidazolium dihydrogen phosphate (BEBzIm-H2PO4). We show structural, physicochemical and electrochemical characterization of synthesized IL and prepared membranes. The addition of IL in composite membranes of ABPBI-H3PO4 increases thermal stability. Also, the conductivity of membranes increases with temperature and the amount of absorbed mixture. Conductivity at a range of 10- 4 S/cm was achieved at 150 C by 50% IL and 50% phosphoric acid impregnation. This conducting composite membrane shows promise for operation in temperature proton exchange membrane fuel cells at working temperatures up to 100 C.
Hernández Carrillo, Rubí,Suarez-Guevara, Jullieth,Torres-González, Luis Carlos,Gómez-Romero, Pedro,Sánchez, Eduardo M.
p. 115 - 120
(2013)
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N-Heterocyclic carbene copper(i), mercury(ii) and silver(i) complexes containing durene linker: Synthesis and structural studies
The dibenzimidazolium salts bis[N-(alkyl)benzimidazoliumylmethyl] durene·2X (1a: alkyl = C2H5, X = Br; 1b: alkyl = C2H5, X = PF6; 1c: alkyl = n-C 3H7, X = Cl; 1d: alkyl = n-Csub
Liu, Qing-Xiang,Chen, Ai-Hui,Zhao, Xiao-Jun,Zang, Yan,Wu, Xiu-Mei,Wang, Xiu-Guang,Guo, Jian-Hua
p. 293 - 305
(2011)
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1D coordination polymers of silver(I) and copper(II) based on bis(N-heterocyclic carbene) ligands: Synthesis and structural studies
The alkyl chain-linked diimidazolium (or dibenzimidazolium) salts, 1,1′-diethyl-4,4′-tetramethylene-diimidazolium-diiodide (L 1H2·I2) and 1,1′-diethyl-3, 3′-trimethylene-dibenzimidazolium-diiodide (L2H 2·I2), and their silver(I) and copper(II) coordination polymers, [L1AgI]n (1) and [L 2Cu2I4]n (2), have been prepared and characterized. Complex 1 is a 1D helical polymer generated by bidentated carbene ligands (L1) and Ag(I) atoms. The 1D polymer of 2 is formed by bidentated carbene ligands (L2) and coplanar quadrilateral Cu 2I2 units. 3D supramolecular frameworks in the crystal packings of 1 and 2 are formed via intermolecular weak interactions, including C-H?π contacts, π-π interactions and C-H?I hydrogen bonds.
Liu, Qing-Xiang,Shi, Meng-Chao,Wang, Zhi-Qiang,Liu, Shu-Wen,Ge, Shu-Sheng,Zang, Yan,Wang, Xiu-Guang,Guo, Jian-Hua
p. 2121 - 2126
(2010)
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Using Methanol as a Formaldehyde Surrogate for Sustainable Synthesis of N-Heterocycles via Manganese-Catalyzed Dehydrogenative Cyclization
The development of an efficient and sustainable synthetic route for formaldehyde production from renewable feedstock, especially in combination with a subsequent transformation to straightforwardly construct valuable chemicals, is highly desirable. Herein, we report a novel manganese-catalyzed dehydrogenative cyclization of methanol as a formaldehyde surrogate with a variety of dinucleophiles for facile synthesis of N-heterocycles. The in situ generated formaldehyde via catalytic methanol dehydrogenation can be selectively trapped by diverse dinucleophiles to avoid several possible side reactions. The utility of this transformation is further highlighted by its successful application to the synthesis of 13C-labeled N-heterocycles using 13CH3OH as a readily accessible 13C-isotope reagent.
Li, Yibiao,Liu, Qiang,Shao, Zhihui,Yuan, Shanshan
supporting information

(2022/02/23)

Methanol as the C1source: Redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles
We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazoles using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher atom, step, and redox economies and exc
An, Jie,Lai, Zemin,Li, Hengzhao,Peng, Mengqi,Sun, Yanhao,Yan, Zihan,Yang, Ruoyan,Zhang, Yuntong
supporting information
p. 748 - 753
(2022/02/02)

Self-Assembly of Benzimidazole-Derived Tris-NHC Ligands and AgI-Ions to Hexanuclear Organometallic Cages and Their Unusual Transmetalation Chemistry
Multi-ligand self-assembly to attain the AgI-N-heterocyclic carbene (NHC)-built hexanuclear organometallic cages of composition [Ag6(3 a,b)4](PF6)6 from the reaction of benzimidazole-derived tris(azolium) salts [H3-3 a,b](PF6)3 with Ag2O was achieved. The molecular structures of the cages were established by X-ray diffraction studies along with NMR and MS analyses. The existence of a single assembly in solution was supported by diffusion-ordered spectroscopy (DOSY) 1H NMR spectra. Further, transmetalation reactions of these self-assembled complexes, [Ag6(3 a,b)4](PF6)6, with CuI/AuI-ions provided various coinage metal-NHC complexes having diverse molecular compositions, which included the first example of a hexanuclear CuI-dodecacarbene complex, [Cu6(3 b)4](PF6)6.
Nishad, Rajeev C.,Rit, Arnab
supporting information
p. 594 - 599
(2020/12/07)

Iodine(I) and Silver(I) Complexes of Benzoimidazole and Pyridylcarbazole Derivatives
The synthesis of iodine(I) complexes with either benzoimidazole or carbazole-derived sp2 N-containing Lewis bases is described, as well as their corresponding silver(I) complexes. The addition of elemental iodine to the linear two-coordinate Ag
Rissanen, Kari,Siepmann, Marcel,Taipale, Essi,Truong, Khai-Nghi
supporting information
p. 17412 - 17419
(2021/10/19)

Highly efficient one pot synthesis of benzimidazoles from 2-nitroaniline and PhSiH3 as reducing agent catalyzed by Pd/C as a heterogeneous catalyst
This work reports an efficient route for the synthesis of benzimidazole from o-nitroaniline in the presence of carbon dioxide atmosphere, PhSiH3 as a reducing agent catalyzed by Pd/C as a catalyst. Benzimidazoles have become the focus of organic chemists, as benzimidazole is an important intermediate in medicinal chemistry. We have developed more efficient route for the synthesis benzimidazole and various substituted benzimidazoles have been synthesized in good to excellent yield. The TBD (1,5,7-Triazabicyclo [4.4.0] dec-5-ene) is selected as a base as it promotes the CO2 insertion. Benzimidazoles were synthesized through reduction of nitro group followed by cyclization of amine using CO2 as a carbon source. Moreover, the Pd/C catalyst can be recycled up to five recycle run without significant changes in the yield of the product.
Phatake, Vishal V.,Bhanage, Bhalchandra M.
(2021/03/15)

Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical
A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to a broad range of benzimidazole and deuterated benzimidazole products in generally high yields with good tolerance of various synthetically and pharmaceutically useful functionalities. The mechanistic studies reveal that both single electron transfer and energy transfer probably occur in the initial step and a sulfinyl radical intermediate is involved in the key desulfurization process.
Deng, Guo-Jun,Fu, Mei,Huang, Huawen,Ji, Xiaochen,Li, Yongtong
supporting information
p. 5594 - 5598
(2020/09/21)

Annular N-heterocycle double-carbene palladium coordination compound and preparation method and application thereof
The invention discloses an annular N-heterocycle double-carbene palladium coordination compound and a preparation method and application thereof. 1,4-2(N-ethyl-benzimidazole onium methyl)-2,3,5,6-tetramethylbenzene arene salt is used as a precursor of the annular N-heterocycle double-carbene palladium coordination compound. The synthetic annular N-heterocycle double-carbene palladium coordinationcompound is used as a catalyst and used for catalyzing the cross-coupling reaction of carbon-carbon bonds. The preparation method of the annular N-heterocycle double-carbene palladium coordination compound comprises the steps that under nitrogen protection, 1,4-2(N-ethyl-benzimidazole onium methyl)-2,3,5,6-tetramethylbenzene arene salt and metal compounds are added to a reaction vessel according to a molar ratio of 1:(2-5), an organic solvent is added to the mixture, then reaction is conducted for 12-24 hours under the temperature of 0-100 DEG C, the mixture is filtered and subjected to etherdiffusion, and the annular N-heterocycle double-carbene palladium coordination compound is obtained. The prepared annular N-heterocycle double-carbene palladium coordination compound is mainly appliedto the technical field of catalysts.
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Paragraph 0023; 0026

(2018/04/26)

Bis-benzimidazolium-palladium system catalyzed Suzuki-Miyaura coupling reaction of aryl bromides under mild conditions
Bis-benzimidazolium salts were prepared successfully from commercially available and inexpensive o-phenylenediamine through a series of simple reactions. The bis-NHC-Pd complexes prepared in situ can catalyze Suzuki-Miyaura cross-coupling reaction under very mild conditions in aqueous media with excellent yields. The efficiency of this reaction is demonstrated by its compatibility with a range of functional groups. Di-ortho-substituted biaryls could be accomplished in 89–99% yields. Moreover, the rigorous exclusion of air or moisture is not required in these transformations.
Lin, Yi-Rang,Chiu, Chien-Cheng,Chiu, Huai-Tsu,Lee, Dong-Sheng,Lu, Ta-Jung
(2017/10/05)

Benzoxazole and dioxolane substituted benzimidazole–based N–heterocyclic carbene–silver(I) complexes: Synthesis, structural characterization and in vitro antimicrobial activity
A novel series of 1,3–benzoxazole and 1,3–dioxolane substituted benzimidazole–based N–heterocyclic carbene (NHC) precursors (6a–b and 11a–b) and their corresponding NHC–silver(I) acetate (12a–b and 14a–b) and bis–NHC–silver(I) hexafluorophosphate complexe
Shahini,Achar, Gautam,Budagumpi, Srinivasa,Müller-Bunz, Helge,Tacke, Matthias,Patil, Siddappa A.
p. 1 - 13
(2018/05/23)

Alkylation method for nitrogen-hydrogen containing compounds and application thereof
The invention discloses an alkylation method for nitrogen-hydrogen containing compounds and an application thereof, belonging to the technical field of synthesis of organic compounds. The invention provides a series of methods for a nitrogen alkylation reaction of N-H containing heterocyclic compounds (II) with N,N-dimethylformamide dialkyl acetal as an alkyl source under the condition of no participation of metals, and a product with a hydrogen atom on a nitrogen atom substituted by R1 is obtained. The method provided by the invention has the advantages of highly-efficient reaction, high yield, simple treatment after the reaction, simple and convenient operation, mild reaction conditions, no participation of the metals, high tolerance of functional groups of a reaction substrate, wide range and easy preparation of the substrate, high reaction efficiency after amplification of the reaction, and applicability to large-scale industrial production.
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Paragraph 0042-0044

(2018/10/04)

Synthesis, characterization and anti-proliferative activity of propylene linked bis-benzimidazolium salts and their respective dinuclear Silver(I)-N-heterocyclic carbene complexes
A new series of propylene linked bis-benzimidazolium salts, 1–4 were reacted with Ag2O to facilitate the formation of their respective dinuclear Ag(I)-N-heterocyclic carbene (NHC) complexes, 5–8 respectively. All compounds were fully characterized by elemental analyses, 1H NMR, 13C NMR and FTIR spectroscopy techniques. The molecular structures of compounds 1 and 6 were elucidated through single crystal X-ray diffraction analyses. Both salts and complexes were tested for anti-cancer potential against breast cancer (MCF-7) cell line. The IC50 values are in the range of 7?±?1–18?±?3?μM show that the complexes 5–8 possess moderate antiproliferative effect while their respective salts 1–4 are found to be inactive against MCF-7?cell line.
Hussaini, Sunusi Y.,Haque, Rosenani A.,Asekunowo, Patrick O.,Abdul Majid,Taleb Agha,Razali, Mohd. R.
p. 56 - 62
(2017/04/21)

Synthesis, structural investigation and antibacterial studies of non–symmetrically p–nitrobenzyl substituted benzimidazole N–heterocyclic carbene–silver(I) complexes
Several new non–symmetrically p–nitrobenzyl substituted benzimidazole–based mono–N–heterocyclic carbene (NHC)–silver(I) acetate (7a–e) and bis–NHC–silver(I) hexafluorophosphate complexes (8a–e) were synthesized by combination of 1–ethyl/1–propyl/1–butyl/1–pentyl/1–hexyl–3–(4–nitrobenzyl)benzimidazolium hexafluorophosphate salts (6a–e) with silver(I) acetate and silver(I) oxide in methanol and acetonitrile, respectively, in good yields. All the benzimidazolium hexafluorophosphate salts (6a–e) and their corresponding NHC–silver(I) complexes (7a–e and 8a–e) were structurally characterized by 1H, 13C NMR, ATR–IR spectrometry and elemental analysis. The solid–state structures of bis–NHC–silver(I) hexafluorophosphate complexes (8c) and (8e) were determined by single crystal X–ray diffraction method. Preliminary in vitro antibacterial potential of all the compounds (6a–e, 7a–e and 8a–e) were studied against six standard bacterial strains; two Gram–positive (Staphylococcus aureus and Bacillus subtilis) and four Gram–negative bacterial species (Escherichia coli, Pseudomonas aeruginosa, Shigella sonnei, and Salmonella typhi) by Kirby–Bauer's disc diffusion method and their Minimum Inhibitory Concentration (MIC) was determined by broth macrodilution method. All the NHC–silver(I) complexes (7a–e and 8a–e) exhibited moderate to high antibacterial activities with MIC ranging between 16.0 and 128.0?μg/mL, whereas benzimidazolium hexafluorophosphate salts (6a–e) demonstrated poor antibacterial potentials.
Shahini,Achar, Gautam,Budagumpi, Srinivasa,Tacke, Matthias,Patil, Siddappa A.
p. 432 - 441
(2017/07/10)

Self-supported N-heterocyclic carbenes and their use as organocatalysts
The study of N-heterocyclic carbenes (NHCs) as organocatalysts has proliferated in recent years, and they have been found to be useful in a variety of reactions. In an attempt to further expand their utility and to study their recyclability, we designed and synthesized a series of self-supported NHCs in which the catalytic carbene groups form part of a densely functionalized polymer backbone, and studied them as organocatalysts. Of the self-Supported NHCs examined, a benzimidazole derived polymer with flexible linkers connecting the catalytic groups was found to be the most efficient organocatalyst in a model benzoin condensation reaction, and thus it was used in a variety of such reactions, including some involving catalyst recycling. Furthermore, it was also used to catalyze a set of redox esterification reactions involving conjugated unsaturated aldehydes. In all of these reactions the catalyst afforded good yield of the desired product and its polymeric nature facilitated product purification.
Ma, Shuang,Toy, Patrick H.
(2016/08/30)

Benzimidazole-based silver(I)-N-heterocyclic carbene complexes as anti-bacterials: Synthesis, crystal structures and nucleic acids interaction studies
A series of new benzimidazolium salts as N-heterocyclic carbene (NHC) precursors has been synthesized. Reactions of these salts with Ag2O with varying metal-to-salt ratio facilitate the formation of a series of new binuclear and mononuclear Ag(I)-NHC complexes. All compounds were characterized using physicochemical and spectroscopic techniques. Single-crystal X-ray diffraction study reveals a binuclear structure for one of the complexes and a mononuclear one for two others. These complexes exist as cationic Ag(I)-NHC complexes with the chelation of carbene carbons to the silver centre in an almost linear manner. The compounds were screened for their anti-bacterial activities against Staphylococcus aureus (ATCC 12600) as a Gram-positive bacterium and Escherichia coli (ATCC 25922) as a Gram-negative bacterium. The results show that both bacteria appear markedly inhibited. Furthermore, the results suggest the possibility of steric variation as a modulation of the anti-bacterial activities. The nuclease activities of the compounds were assessed using gel electrophoresis and the results indicate that these complexes can cleave or degrade DNA and RNA via a non-oxidative mechanism.
Asekunowo, Patrick O.,Haque, Rosenani A.,Razali, Mohd. R.,Budagumpi, Srinivasa
p. 126 - 137
(2015/03/30)

Cation does matter: How cationic structure affects the dissolution of cellulose in ionic liquids
As a kind of promising solvents, ionic liquids (ILs) have been used to dissolve cellulose and great progress has been made in recent years. However, the dissolution mechanism, especially the role of cations of ILs in the dissolution of cellulose, is still in debate. In this work, 13 kinds of ILs with a fixed anion [CH3COO]- but varied cationic backbones and alkyl chains have been prepared and characterized. The solubilities of cellulose in these ILs were measured at different temperatures. This allowed us to systematically study the effect of cationic structures on the cellulose dissolution at a given temperature. In order to investigate the dissolution mechanism, Kamlet-Taft parameters of these ILs in the temperature range from 25 to 65 °C and 13C NMR spectra of 1-benzyl-3-methylimidazolium acetate ([phC1mim][CH3COO]) + cellulose systems at 90 °C were also determined. It was found that acidic protons on the heterocyclic rings of the cations are essential for the dissolution of cellulose in the ILs, but the van der Waals interaction of cation with cellulose is not important. These protons may form C-H...O hydrogen bonds with hydroxyl and ether oxygen of cellulose to increase cellulose solubility. Cations of the ILs may also decrease cellulose solubility by strong interaction with anions or steric hindrance effect of large size group in their alkyl chains. These interactions together with strong O-H...O hydrogen bonds between the anion and hydroxyl protons of cellulose resulted in the disruption of the inter- and intra-molecular hydrogen bonds and thus effective dissolution of cellulose.
Lu, Benlian,Xu, Airong,Wang, Jianji
p. 1326 - 1335
(2014/03/21)

Carboxyl-functionalized ionic liquids based on Benzimidazolium cation: Study of Hammett values and catalytic activity towards one-pot synthesis of 1-amidoalkyl naphthols
A series of new carboxyl-functionalized benzimidazolium based ionic liquids (CFBILs) were synthesized and characterized by FT-IR, NMR and HR-MS (EI). Catalytic activities of CFBILs were evaluated towards the solvent free, one-pot synthesis of 1-amidoalkyl
Muskawar, Prashant Narayan,Senthil Kumar,Bhagat, Pundlik Rambhau
p. 112 - 117
(2013/11/19)

A general method for the preparation of N-heterocyclic carbene-silver(I) complexes in water
A new synthetic method leading to N-heterocyclic carbene-silver(I) complexes [(R2-NHC)2Ag]+ [AgX2] - is developed by using benzimidazolium compounds, NaOH (as a base), silver salts and water (as the reaction medium). Single-crystal X-ray structure revealed that compound 1 comprises a linear [Ag-(Et2-Bimy) 2]+ cation and a linear [AgBr2]- anion. These two ions are linked through an AgI-AgI association and staggered at an angle of 90.3.
Saif, Muhammad Jawwad,Flower, Kevin R.
p. 113 - 118
(2013/08/24)

Properties of alkylbenzimidazoles for CO2 and SO2 capture and comparisons to ionic liquids
To date, few reports have been concerned with the physical properties of the liquid phases of imidazoles and benzimidazolespotential starting materials for a great number of ionic liquids. Prior research has indicated that alkylimidazole solvents exhibit different, and potentially advantageous physical properties, when compared to corresponding imidazolium-based ionic liquids. Given that even the most fundamental physical properties of alkylimidazole solvents have only recently been reported, there is still a lack of data for other relevant imidazole derivatives, including benzimidazoles. In this work, we have synthesized a series of eight 1-n-alkylbenzimidazoles, with chain lengths ranging from ethyl to dodecyl, all of which exist as neat liquids at ambient temperature. Their densities and viscosities have been determined as functions of both temperature and molecular weight. Alkylbenzimidazoles have been found to exhibit viscosities that are more similar to imidazolium-based ILs than alkylimidazoles, owed to a large contribution to viscosity from the presence of a fused ring system. Solubilities of CO2 and SO2, two species of concern in the emission of coal-fired power generation, were determined for selected alkylbenzimidazoles to understand what effects a fused ring system might have on gas solubility. For both gases, alkylbenzimidazoles were determined to experience physical, non-chemically reactive, interactions. The solubility of CO2 in alkylbenzimidazoles is 10%-30% less than observed for corresponding ILs and alkylimidazoles. 1-butylbenzimidazole was found to readily absorb at least 0.333 gram SO2 per gram at low pressure and ambient temperature, which could be readily desorbed under an N2 flush, a behavior more similar to imidazolium-based ILs than alkylimidazoles. Thus, we find that as solvents for gas separations, benzimidazoles share characteristics with both ILs and alkylimidazoles. Science China Press and Springer-Verlag Berlin Heidelberg 2012.
Shannon, Matthew S.,Hindman, Michelle S.,Danielsen, Scott P.O.,Tedstone, Jason M.,Gilmore, Ricky D.,Bara, Jason E.
p. 1638 - 1647
(2012/10/30)

Synthesis and characterization of ortho-Xylyl linked bis-benzimidazolium salts
A number of N-alkylbenzimidazoles were synthesized by reactions of benzimidazole with alkyl halides (i-prBr, BuCl, BzCl, HeptBr, EtBr, PrBr). The subsequent treatment of the resulting N-alkylzoles with 1,2-bis(bromomethylene) benzene afforded corresponding bisbenzimidazolium salts. All the compounds were characterized by spectroscopic techniques (NMR and FT-IR) and microanalysis.
Haque, Rosenani A.,Iqbal, Muhammad Adnan
scheme or table
p. 2625 - 2628
(2012/08/27)

Indole RSK inhibitors. Part 2: Optimization of cell potency and kinase selectivity
A series of inhibitors for the 90 kDa ribosomal S6 kinase (RSK) based on an 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide scaffold were optimized for cellular potency and kinase selectivity. This led to the identification of compound 24, BIX 02565, an attractive candidate for use in vitro and in vivo to explore the role of RSK as a target for the treatment heart failure.
Kirrane, Thomas M.,Boyer, Stephen J.,Burke, Jennifer,Guo, Xin,Snow, Roger J.,Soleymanzadeh, Lida,Swinamer, Alan,Zhang, Yunlong,Madwed, Jeffery B.,Kashem, Mohammed,Kugler, Stanley,O'Neill, Margaret M.
p. 738 - 742
(2012/03/11)

Mercury (II), copper (II) and silver (I) complexes with ether or diether functionalized bis-NHC ligands: Synthesis and structural studies
The oligoether-linked dibenzimidazolium (or diimidazolium) salts, bis[2-(3-ethylbenzimidazolium-1-yl)ethyl]ether diiodide (1), bis[2-(3- nbutylbenzimidazolium-1-yl)ethyl]ether diiodide (2), 1,1′-[1,2-ethanediyl-bis(oxy-1,2-ethanediyl)]-bis(3-benzylbenzimidazolium- 1-yl) diiodide (3), 1,1′-[1,2-ethanediyl-bis(oxy-1,2-ethanediyl)]-bis(3- ethylbenzimidazolium-1-yl) di-hexafluorophosphate (4), 1,1′-[1,2- ethanediyl-bis(oxy-1,2-ethanediyl)]-bis(3-benzylimidazolium-1-yl) diiodide (5), and their five mercury(ii), copper(ii) and silver(i) complexes with ether or diether linkers mercury-{C,C′-bis[2-(3-ethylimidazolin-2-yliden-1-yl) ethyl]ether} tetraiodomercurate (7), copper-{C,C′-bis[2-(3- nbutylimidazolin-2-yliden-1-yl)ethyl]ether} tetraiodomercurate (8), mercury-{C,C′-1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] -bis(3-benzylbenzimidazolin-2-yliden-1-yl)} triiodomercurate acetate (9), silver-{C,C′-1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] -bis(3-ethylbenzimidazolin-2-yliden-1-yl)} hexafluorophosphate (10) and mercury-{C,C′-1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)] -bis(3-benzylimidazolin-2-yliden-1-yl)} tetraiodomercurate (11), as well as one anionic complex bis[2-(3-nbutylbenzimidazolium-1-yl)ethyl]ether di-μ-iodo-bis(diiodomercurate) (6) were prepared and characterized. Each of N-heterocyclic carbene metal complexes 7-11 possesses a macrometallocycle, respectively, formed by one metal atom and one bidentate chelate carbene ligand. In the crystal packing of complexes 6-11, 2D supramolecular layers are formed via intermolecular weak interactions, including π-π interactions, hydrogen bonds, C-H...π contacts and weak Hg...I bonds.
Liu, Qing-Xiang,Yu, Jie,Zhao, Xiao-Jun,Liu, Shu-Weng,Yang, Xiao-Qiong,Li, Kang-Ying,Wang, Xiu-Guang
experimental part
p. 4086 - 4096
(2012/05/07)

Mild and general one-pot reduction and cyclization of aromatic and heteroaromatic 2-nitroamines to bicyclic 2 H -imidazoles
A one-pot procedure for the conversion of aromatic and heteroaromatic 2-nitroamines into bicyclic 2H-benzimidazoles is described. The procedure employs formic acid, iron powder, and an additive such as NH4Cl to reduce the nitro group and effect the imidazole cyclization with high-yielding conversions generally within one to two hours. The compatibility with a wide range of functionality demonstrates the general utility of this procedure.
Hanan, Emily J.,Chan, Bryan K.,Estrada, Anthony A.,Shore, Daniel G.,Lyssikatos, Joseph P.
experimental part
p. 2759 - 2764
(2010/12/25)

New mercury(II) and silver(I) complexes containing NHC metallacrown ethers with the π-π stacking interactions
The oligoether-linked bis-benzimidazolium salt 1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)]bis[(3-secbutyl)benzimidazolium-1-yl]iodide (H2L1 · I2), 1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)]bis[(3-ethyl)benzimidazolium-1-yl]iodide (H2L2 · I2) and 1,1′-[1,2-ethanediylbis(oxy-1,2-ethanediyl)]bis[(3-secbutyl)benzimidazolium-1-yl]hexafluorophosphate (H2L1 · (PF6)2) and their three new mercury(II) and silver(I) complexes containing NHC metallacrown ethers, HgL1 · (Hg2 · I6) (1), HgL2 · I2 (2) and AgL1 · PF6 (3) were prepared and characterized. In the packing diagrams of H2L2 · I2, 1, 2 and 3 benzimidazole ring head-to-tail π-π stacking interactions are observed.
Liu, Qing-Xiang,Zhao, Xiao-Jun,Wu, Xiu-Mei,Guo, Jian-Hua,Wang, Xiu-Guang
p. 5671 - 5679
(2008/03/18)

Benzimidazole and indole derivatives as CRF receptor modulators
Benzimidazole and indole derivatives that act as selective modulators of CRF 1 receptors are provided. These compounds are useful in the treatment of a number of CNS and periphereal disorders, particularly stress, anxiety, depression, cardiovascular disorders, and eating disorders. Methods of treatment of such disorders and well as packaged pharmaceutical compositions are also provided. Compounds of the invention are also useful as probes for the localization of CRF receptors and as standards in assays for CRF receptor binding. Methods of using the compounds in receptor localization studies are given.
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(2008/06/13)

Viral polymerase inhibitors
A compound of the formula I: wherein: X is CH or N; Y is O or S; Z is OH, NH2, NMeR3, NHR3; OR3 or 5- or 6-membered heterocycle, having 1 to 4 heteroatoms selected from 0, N and S, said heterocycle being optionally substituted with from 1 to 4 substituents; A is N, COR7 or CR5, wherein R5 is H, halogen, or (C1-6) alkyl and R7 is H or (C1-6 alkyl), with the proviso that X and A are not both N; R6 is H, halogen, (C1-6 alkyl) or OR7, wherein R7 is H or (C1-6 alkyl); R1 is selected from the group consisting of 5- or 6-membered heterocycle having 1 to 4 heteroatoms selected from O, N, and S, phenyl, phenyl(C1-3)alkyl, (C2-6)alkenyl, phenyl(C2-6)alkenyl, (C3-6)cycloalkyl, (C1-6)alkyl, CF3, 9- or 10-membered heterobicycle having 1 to 4 heteroatoms selected from O, N and S, wherein said heterocycle, phenyl, phenyl(C2-6)alkenyl and phenyl(C1-3)alkyl), alkenyl, cycloalkyl, (C1-6)alkyl, and heterobicycle are all optionally substituted with from 1 to 4 substituents R2 is selected from (C1-6)alkyl, (C3-7)cycloalkyl, (C3-7)cycloalkyl(C1-3)alkyl, (C6-10)bicycloalkyl, adamantyl, phenyl, and pyridyl, all of which is optionally substituted with from1 to 4 substituents; R3 is selected from H, (C1-6)alkyl, (C3-6)cycloalkyl, (C36)cycloalkyl(C1-6)alkyl, (C6-10)aryl, (C6-10)aryl(C1-6)alkyl, (C2-6)alkenyl, (C3-6)cycloalkyl(C2-6)alkenyl, (C6-10)aryl(C2-6)alkenyl, N{(C1-6)alkyl}2, NHCOO(C1-6)alkyl(C6-10)aryl, NHCO(C6-10)aryl, (C1-6)alkyl-5- or 10-atom heterocycle, having 1 to 4 heteroatoms selected from O, N and S, and 5- or 10-atom heterocycle having 1 to 4 heteroatoms selected from O, N and S; wherein said alkyl, cycloalkyl, aryl, alkenyl and heterocycle are all optionally substituted with from 1 to 4 substituents; n is zero or 1; or a detectable derivative or salt thereof. The compounds of the invention may be used as inhibitors of hepatitis C virus replication. The invention further provides a method for treating or preventing hepatitis C virus infection.
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(2008/06/13)

METALLATION OF 1-DIALKYLAMINOBENZIMIDAZOLES
In contrast to 1-amino- and 1-alkylaminobenzimidazoles, 1-di-alkylaminobenzimidazoles are metallated by n-butyl-lithium in absolute ether at the 2-position.The subsequent treatment of the lithium derivatives by electrophilic reagents, in which role benzop
Kuz'menko, V. V.,Filatova, I. A.,Pozharskii, A. F.
p. 1009 - 1014
(2007/10/02)

A NEW ROUTE TO N-ALKYL-o-PHENYLENEDIAMINES UTILISING N-ALKYL-2,1,3-BENZOTHIADIAZOLIUM SALTS AND THEIR SELENIUM ANALOGUES
The alkyl quaternary salts of 2,1,3-benzothiadiazole and 2,1,3-benzoselenadiazole undergo facile ring-opening to produce the corresponding N-alkyl-o-phenylenediamines.
Ralph, J. T.
p. 1381 - 1388
(2007/10/02)

REGIOSELECTIVE N-ALKYLATION OF BENZIMIDAZOLE VIA AN ORGANOTIN ROUTE
A simple and efficient method for the exclusive N-alkylation of benzimidazole with functional group compatibility has been achieved.
Soundararajan, R.,Balasubramanian, T.R.
p. 5555 - 5558
(2007/10/02)

REDUCTION OF BENZIMIDAZOLE-2-SULFONIC ACIDS
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Popov, I. I.,Boroshko, S. L.,Tertov, B. A.
p. 224
(2007/10/02)

A New Method for N-Alkylation of Imidazoles and Benzimidazoles
Die N-Alkylierung von Imidazolen und Benzimidazolen in Zwei-Phasen-Systemen (fluessig/fluessig und fluessig/fest) wird beschrieben.
Pilarski, Boguslaw
p. 1078 - 1080
(2007/10/02)

N-Alkylation of Pyrrole, Indole, and Several Other Nitrogen Heterocycles Using Potassium Hydroxide as a Base in the Presence of Polyethylene Glycols or Their Dialkyl Ethers
The alkylation of pyrrole and indole in aqueous potassium hydroxide-organic two-phase systems in the presence of polyethylene glycols (PEG) or their dialkyl ethers (PEG-ether) as phase transfer catalysts (PTC) gave substantial quantities of the C-alkylated and C,N-polyalkylated products as well as the N-alkylated products.This fact is similar to that obtained in the presence of quaternary ammonium salts as PTC.In powdered potassium hydroxide-organic two-phase system, the yields of the N-alkylated products were generally high.Especially, when PEG-ether were employed as solvents, the N-alkylated products were obtained in excellent yields under mild conditions.Imidazole, benzimidazole, carbazole, 2-methylindole, and benzotriazole were similarly N-alkylated in high yields by this method.
Sukata, Kazuaki
p. 280 - 284
(2007/10/02)