1019-85-8Relevant articles and documents
Preparation, characterization, and application of 1,1′-disulfo-[2,2′-bipyridine]-1,1′-diium chloride ionic liquid as an efficient catalyst for the synthesis of benzimidazole derivatives
Shirini, Farhad,Abedini, Masoumeh,Seddighi, Mohadeseh,Arbosara, Fatemeh Shaabani
, p. 7683 - 7693 (2015)
In this study, 2,2′-bipyridine was treated with chlorosulfonic acid and 1,1′-disulfo-[2,2′-bipyridine]-1,1′-diium chloride, [BiPy](SO3H)2Cl2, as a new ionic liquid catalyst was obtained and characterized with a variety of techniques including IR, 1H, and 13C NMR, Hammett acidity function as well as mass spectra method. After preparation and characterization, this ionic liquid was used as an efficient catalyst for the green and mild synthesis of benzimidazole derivatives. In addition, this reagent is efficiently able to catalyze the preparation of benzimidazole derivatives from the protected derivatives of aldehydes including oximes and semicarbazones. All reactions are performed under mild conditions in excellent yields.
VO(acac)2 catalyzed condensation of o-phenylenediamine with aromatic carboxylic acids/aldehydes under microwave radiation affording benzimidazoles
Dey, Madhudeepa,Deb, Krishnajyoti,Dhar, Siddhartha Sankar
, p. 296 - 299 (2011)
Vanadyl acetylacetonate, VO(acac)2, has been found to be very effective catalyst for synthesis of a variety of benzimidazoles under solvent-free condition. The methodology involves the exposure of a mixture of o-phenylenediamine and a selected aromatic carboxylic acid/aldehyde to microwave radiation without the use of any solvent or supporting agents. The benzimidazoles were obtained in quick time with high yields.
UV-visible light-induced photochemical synthesis of benzimidazoles by coomassie brilliant blue coated on W-ZnO@NH2nanoparticles
Chen, Ruijuan,Jalili, Zahra,Tayebee, Reza
, p. 16359 - 16375 (2021)
Heterogeneous photocatalysts proffer a promising method to actualize eco-friendly and green organic transformations. Herein, a new photochemical-based methodology is disclosed in the preparation of a wide range of benzimidazoles through condensation of o-phenylenediamine with benzyl alcohols in the air under the illumination of an HP mercury lamp in the absence of any oxidizing species catalyzed by a new photocatalyst W-ZnO@NH2-CBB. In this photocatalyst, coomassie brilliant blue (CBB) is heterogenized onto W-ZnO@NH2 to improve the surface characteristics at the molecular level and enhance the photocatalytic activity of both W-ZnO@NH2 and CBB fragments. This unprecedented heterogeneous nanocatalyst is also identified by means of XRD, FT-IR, EDS, TGA-DTG, and SEM. The impact of some influencing parameters on the synthesis route and effects on the catalytic efficacy of W-ZnO@NH2-CBB are also assessed. The appropriate products are attained for both the electron-withdrawing and electron-donating substituents in the utilized aromatic alcohols. Furthermore, preparation of benzimidazoles is demonstrated to occur mainly via a radical mechanism, which shows that reactive species such as ·O2-, OH and h+ would be involved in the photocatalytic process. Stability and reusability studies also warrant good reproducibility of the nanophotocatalyst for at least five runs. Eventually, a hot filtration test proved that the nanohybrid photocatalyst is stable in the reaction medium. Using an inexpensive catalyst, UV-vis light energy and air, as a low cost and plentiful oxidant, puts this methodology in the green chemistry domain and energy-saving organic synthesis strategies. Finally, the anticancer activity of W-ZnO nanoparticles is investigated on MCF7 breast cancer cells by MTT assay. This experiment reveals that the mentioned nanoparticles have significant cytotoxicity towards the selected cell line.
One-pot synthesis of benzoazoles via dehydrogenative coupling of aromatic 1,2-diamines/2-aminothiophenol and alcohols using Pd/Cu-MOF as a recyclable heterogeneous catalyst
Mokhtari, Javad,Hasani Bozcheloei, Abolfazl
, p. 726 - 731 (2018)
In this paper we report an efficient synthetic approach for the preparation of the widespread numbers of benzoazoles via dehydrogenative coupling of 1,2-phenylenediamine or 2-aminothiophenol and benzyl alcohols by Pd/Cu2(BDC)2(DABCO)-MOF as new heterogeneous catalyst under solvent-free condition. The catalyst recycled and reused for four times without loss of catalytic activity. The structures of benzoazoles were corroborated spectroscopically (1H- and 13C NMR, and elemental analysis) and were confirmed by comparison with reference compounds. A plausible mechanism for this type of reaction is proposed.
Microwave irradiation synthesis of 2-substituted benzimidazoles using PPA as a catalyst under solvent-free conditions
Lu, Jun,Yang, Bingqin,Bai, Yinjuan
, p. 3703 - 3709 (2002)
An efficient microwave irradiation synthesis of 2-substituted benzimidazoles using polyphosphoric acid (PPA) as a catalyst from organic acid and o-phenylenediamine under solvent-free conditions is described. This method is a good option to obtain the title compounds in a simple and an inexpensive way.
Green and efficient methods for one-pot aerobic oxidative synthesis of benzimidazoles from alcohols with TEMPO-PEG 4000-NHC-Cu(II) complex in water
Wang, Zhao-Gang,Cao, Xiao-Hua,Yang, Yao,Lu, Ming
, p. 1476 - 1483 (2015)
In this article, an amphiphilic catalyst TEMPO-PEG4000-NHC-Cu(II) [2,2,6,6-tetramethylpiperidine-1-oxyl/polyethylene glycol/N-heterocyclic carbene] complex was synthesized and used as a highly efficient catalyst for one-pot aerobic oxidative synthesis of benzimidazoles from alcohols. The reactions were applicable in water with good yields in the presence of catalyst (5 mol%). Moreover, the catalyst was easily recovered from the reaction mixture and reused with almost consistent activity.
Eco-friendly synthesis of benzimidazole derivatives using solid acid scolecite catalyst
Gadekar, Lakshman S.,Arbad, Balasaheb R.,Lande, Machhindra K.
, p. 1053 - 1056 (2010)
A series of benzimidazole derivatives were synthesized expeditiously in good yields by condensation of 1,2-diaminobenzene and aromatic aldehydes in the presence of modified scolecite catalyst. The world wide availability, easy handling and reusability of catalyst, higher yields and shorter reaction times are the advantages of the present method.
Copper-catalyzed intramolecular C-N bond formation: A straightforward synthesis of benzimidazole derivatives in water
Peng, Jinsong,Ye, Min,Zong, Cuijuan,Hu, Fangyun,Feng, Lingtong,Wang, Xiaoyan,Wang, Yufeng,Chen, Chunxia
, p. 716 - 719 (2011)
A straightforward, efficient, and more sustainable copper-catalyzed method has been developed for intramolecular N-arylation providing the benzimidazole ring system. With Cu2O (5 mol %) as the catalyst, DMEDA (10 mol %) as the ligand, and K2CO3 as the base, this protocol was applied to synthesize a small library of benzimidazoles in high yields. Remarkably, the reaction was exclusively carried out in water, rendering the methodology highly valuable from both environmental and economical points of view.
Aerobic oxidative synthesis of 2-arylbenzimidazoles, 2-arylbenzoxazoles, and 2-arylbenzothiazoles from arylmethanols or arylmethylamines catalyzed by Fe(III)/TEMPO under solvent-free conditions
Yu, Jiatao,Shen, Mengnan,Lu, Ming
, p. 771 - 778 (2015)
A simple and efficient aerobic oxidative synthesis of 2-arylbenzimidazoles, 2-arylbenzoxazoles, and 2-arylbenzothiazoles from arylmethanols or arylmethylamines with o-phenylenediamine, o-aminophenol and o-aminothiophenol catalyzed by Fe2(SO4)3/TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxyl) system under solvent-free conditions. This reaction uses air as an environmental and economic oxidant, tolerates a variety of functional groups on the aromatic ring of the benzylic partner, and affords the products in moderate yields.
Highly chemoselective synthesis of benzimidazoles in Sc(OTf)3-catalyzed system
Fan, Liyan,Kong, Lulu,Chen, Wen
, p. 2306 - 2314 (2015)
The present researches elicit a simple, green and efficient method for the synthesis of substituted benzimidazoles through the coupling of o-phenylenediames with aldehydes catalyzed by Sc(OTf)3 in ethanol, which obtains high chemoselectivity and excellent yield of many biologically active 1,2-disubstitued and 2-substituted benzimidazoles respectively and are also environment friendly.
An unexpected role of carbon disulfide: A new and efficient method for the synthesis of 2-substituted benzimidazoles
Gladysz, John A.,Safaei, Hamid Reza,Nouri, Sara
, p. 1539 - 1545 (2014)
A new and efficient methodology for the synthesis of 2-substituted benzimidazoles is described. In this procedure, CS2 unexpectedly facilitated the cyclization reaction between benzene-1,2-diamine and benzenecarbaldehydes in CH2Clsu
Nanoparticle mediated organic synthesis (NAMO-synthesis): CuI-NP catalyzed ligand free amidation of aryl halides
Kumar, Atul,Bishnoi, Ajay Kumar
, p. 41631 - 41635 (2014)
The first CuI-nanoparticle catalyzed ligand free synthesis of N-aryl amides from aryl halides and arylamides/cyclic amides has been developed. This methodology is further extended for the synthesis of nitrogen heterocycles such as benzimidazole, and quinazolinone via intermolecular amidation reaction followed by cyclization. TEM images of the CuI-NP catalyst showed spherical, well-dispersed particles which provide large surface area for reactivity and have good recyclability. This journal is
Efficient aerobic oxidative synthesis of benzimidazoles with Fe(III) based PEG1000 dicationic imidazolium ionic liquid/toluene temperature-dependent biphasic system
Wang, Zhao-Gang,Xia, Yong-Gen,Jin, Yong,Lu, Ming
, p. 103 - 106 (2015)
A green protocol for the synthesis of benzimidazoles with Fe(III) based PEG1000 dicationic imidazolium ionic liquid ([PEG1000mim2][FeCl4]2)/toluene temperature-dependent biphasic system was described. Conformed by IR analysis, FeCl4-is the dominating anion species. It could be seen that aldehydes arylamines and aromatic aldehydes bearing electron-deficient group (-Cl,-Br,-NO2) and electron-rich groups(-OH, -N(CH3)2) on the aromatic rings gave good yields (78-96%). Moreover, the Fe(III) based PEG1000 dicationic imidazolium ionic liquid could be recycled and reused without significant loss of catalytic activity after seven runs.
Isocyanurate-based periodic mesoporous organosilica (PMO-ICS): A highly efficient and recoverable nanocatalyst for the one-pot synthesis of substituted imidazoles and benzimidazoles
Dekamin, Mohammad G.,Arefi, Elham,Yaghoubi, Amene
, p. 86982 - 86988 (2016)
Isocyanurate bridging periodic mesoporous organosilica (PMO-ICS) was shown to be a highly active and efficient recyclable catalyst for the three-component synthesis of imidazole derivatives from benzoin, different aldehydes and ammonium acetate under mild reaction conditions in short reaction times and good to excellent yields in EtOH. Also, benzimidazole derivatives were efficiently prepared from o-phenylenediamine and different aldehydes in the presence of PMO-ICS. Moreover, the catalyst was also recovered and reused at least four times without a significant decrease in its activity. The PMO-ICS catalyst was characterized by Fourier transformer infrared (FTIR) spectroscopy, thermogravimetry analysis (TGA), powder X-ray diffraction (XRD) and nitrogen adsorption-desorption isotherm (NADI) techniques as well as field emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM). Compared to the classical methodologies, this method illustrated significant advantages including low loading of the catalyst, avoiding the use of toxic transition metals or reactive reagents for modification of the catalytic activity, short reaction times, high to excellent yields, easy separation and purification of the products, and reusability of the catalyst.
Metallovesicles as smart nanoreactors for green catalytic synthesis of benzimidazole derivatives in water
Kaur, Navneet,Kaur, Simranpreet,Kaur, Gurpreet,Bhalla, Aman,Srinivasan, Sesha,Chaudhary, Ganga Ram
, p. 17306 - 17314 (2019)
Metallovesicles are an emerging class of soft nanomaterials where spherical bilayer membranes, resulting from self-aggregation of amphiphilic metal complexes, amalgamate the advantages of metal specific catalytic properties and small hydrophobic cavities
An efficient and reusable heterogeneous catalyst Animal Bone Meal for facile synthesis of benzimidazoles, benzoxazoles, and benzothiazoles
Riadi, Yassin,Mamouni, Rachid,Azzalou, Rachid,Haddad, Mohammadine El,Routier, Sylvain,Guillaumet, Gérald,Lazar, Sa?d
, p. 3492 - 3495 (2011)
A library of benzimidazoles, benzoxazoles, and benzothiazoles was efficiently synthesized by condensation of o-phenylenediamine, o-aminophenol, and o-aminothiophenol respectively with aromatic aldehydes in the presence of catalytic amounts of Animal Bone Meal (ABM) and Lewis acids doped ABMs. Reactions were conducted under reflux conditions in air. The remarkable features of this new protocol are high conversion, short reaction times, and cleaner reaction profiles, straightforward procedure, and reduction in catalyst toxicity.
Synthesis of 2-substituted benzimidazoles and benzothiazoles using Ag2CO3/Celite as an efficient solid catalyst
Soleimani, Ebrahim,Khodaei, Mohammad Mehdi,Yazdani, Hossein,Saei, Parisa,Zavar Reza, Javad
, p. 1281 - 1285 (2015)
An efficient and simple approach for the synthesis of 2-substituted benzimidazoles and benzothiazoles through a coupling of 1,2-phenylenediamines and 2-aminothiophenols with variety of aryl aldehydes in ethanol at 70 °C using Ag2CO3/Celite as solid catalyst is described. The procedure features short reaction time, excellent yields and simple workup.
Synthesis of benzimidazoles by copper-catalyzed aerobic oxidative domino reaction of 1,2-diaminoarenes and arylmethyl halides
Qiu, Dezhi,Wei, Haidong,Zhou, Lihong,Zeng, Qingle
, p. 109 - 112 (2014)
Arylmethyl halides are readily synthesized via halogenation from the basic raw materials, even in green processes. They are used to replace their downstream products to prepare medicinally important 2-aryl benzimidazoles. CuBr-catalyzed synthesis of 2-aryl benzimidazoles from arylmethyl halides and 1,2-diaminoarenes via a one-pot domino reaction is developed. This new synthetic method is simple, practical and cost saving, and tolerates wide functional groups. A mechanism of CuBr-catalyzed aerobic oxidative domino reaction via a one-pot four-step process is proposed.
Zirconocene catalyzed synthesis of 2-substituted benzimidazole derivatives
Karhale, Shrikrishna,Patil, Kiran,Bhenki, Chandrakant,Rashinkar, Gajanan,Helavi, Vasant
, p. 7257 - 7268 (2016)
Abstract: Zirconocene dichloride (Cp2ZrCl2) in the presence of ethanol is found to be a highly efficient catalyst for the one-pot synthesis of structurally diverse 2-substituted benzimidazole derivatives by reaction of o-phenylenedia
Redox-Neutral Photocatalytic Radical Cascade Cyclization for the Synthesis of CH2CN/CF2COOEt/CF3-Containing Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5 H)-One Derivatives
Liu, Liang,Yang, De-Yong,He, Yan-Hong,Guan, Zhi
, p. 11892 - 11901 (2020)
A novel method for the synthesis of benzo[4,5]imidazo[2,1-A]isoquinolin derivatives via visible-light-induced radical cascade cyclization is described. By using N-methacryloyl-2-phenylbenzoimidazoles and diverse radical precursors, various benzo[4,5]imidazo[2,1-A]isoquinolin derivatives containing CH2CN/CF2COOEt/CF3 can be formed in good to excellent yields under mild reaction conditions. This method exhibits good functional group tolerance and a wide range of substrate scope.
Ytterbium perfluorooctanesulfonates catalyzed synthesis of benzimidazole derivatives in fluorous solvents
Shen, Ming-Gui,Cai, Chun
, p. 232 - 235 (2007)
Catalytic condensation of o-phenylenediamine and aldehydes was accomplished using rare earth(III)perfluorooctane sulfonates (RE(OPf)3), RE = Sc, Y, La ～ Lu) as catalysts in fluorous solvents. Ytterbium perfluorooctanesulfonates (Yb(OPf)3) catalyzes the high-efficient synthesis of benzimidazole derivatives in fluorous solvents. By simple separation, fluorous phase containing only catalyst can be reused several times.
Construction of Benzimidazoles and Benzoxazoles through the Molybdenum-Mediated Carbonylation of Aryl Halides
Kebede, Eshetu,Tadikonda, Ramu,Nakka, Mangarao,Inkollu, Bhargavi,Vidavalur, Siddaiah
, p. 5929 - 5933 (2015)
The facile and efficient one-pot construction of benzimidazoles and benzoxazoles through the Mo(CO)6-mediated carbonylation of aryl halides was examined. In the process, Mo(CO)6 acted as a convenient and safe solid source of carbon monoxide. A wide range of substrates were tolerated to provide the corresponding products in fair to good yields without the need of gaseous CO or palladium catalysts. The facile and efficient one-pot construction of benzimidazoles and benzoxazoles is described. The reaction proceeds through Mo(CO)6-mediated carbonylation of aryl halides, in which Mo(CO)6 acts as a convenient and safe solid source of carbon monoxide.
A one-pot synthesis of benzimidazoles via aerobic oxidative condensation of benzyl alcohols with o-phenylenediamines catalyzed by [MIMPs]+Cl-/NaNO2/TEMPO
Geng, Zhenzhen,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan
, p. 557 - 565 (2020)
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.
Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles
Bahrami, Kiumars,Khodaei, Mohammad M.,Nejati, Akbar
, p. 1237 - 1241 (2010)
A practical and convenient synthetic method has been developed for the facile synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles. The method described has the benefits of operational simplicity, excellent yields, and high chemoselectivity. The Royal Society of Chemistry 2010.
Synthesis, bioevaluation and docking studies of some 2-phenyl-1H-benzimidazole derivatives as anthelminthic agents against the nematode Teladorsagia circumcincta
Escala, Nerea,Valderas-García, Elora,Bardón, María álvarez,Gómez de Agüero, Verónica Castilla,Escarcena, Ricardo,López-Pérez, José Luis,Rojo-Vázquez, Francisco A.,San Feliciano, Arturo,Bala?a-Fouce, Rafael,Martínez-Valladares, María,Olmo, Esther del
, (2020)
Gastrointestinal nematode infections are the main diseases in herds of small ruminants. Resistance to the main established drugs has become a worldwide problem. The purpose of this study is to obtain and evaluate the in vitro ovicidal and larvicidal activity of some 2-phenylbenzimidazole derivatives on susceptible and resistant strains of Teladorsagia circumcincta. Compounds were prepared by known procedures from substituted o-phenylenediamines and arylaldehydes or intermediate sodium 1-hydroxyphenylmethanesulfonate derivatives. Egg Hatch Test (EHT), Larval Mortality Test (LMT) and Larval Migration Inhibition Test (LMIT) were used in the initial screening of compounds at 50 μM concentration, and EC50 values were determined for the most potent compounds. Cytotoxicity evaluation of compounds was conducted on human Caco-2 and HepG2 cell lines to calculate their Selectivity Indexes (SI). At 50 μM concentration, nine out of twenty-four compounds displayed more than 98% ovicidal activity on a susceptible strain, and four of them showed more than 86% on one resistant strain. The most potent ovicidal benzimidazole (BZ) 3 showed EC50 = 6.30 μM, for the susceptible strain, while BZ 2 showed the lowest EC50 value of 14.5 μM for the resistant strain. Docking studies of most potent compounds in a modelled Teladorsagia tubulin indicated an inverted orientation for BZ 1 in the colchicine binding site, probably due to its fair interaction with glutamic acid at codon 198, which could justify its inactivity against the resistant strain of T. circumcincta.
An Unexpected Formation of 2-Arylbenzimidazoles from α,α-Diiodo-α’-acetoxyketones and o-Phenylenediamines
Sadhukhan, Santu,Mondal, Swagata,Baire, Beeraiah
, (2022/03/01)
An unusual reactivity of the α,α-diiodo-α’-acetoxyketones with o-phenylenediamines is reported through the formation of 2-arylbenzimidazoles. A systematic study through a series of fruitful control experiments and isolation of key intermediates unravelled the unprecedented domino mechanism. This process involves a stepwise two-carbon fragmentation pathway through domino and sequential amidation–aziridination–decarbonylation–I2-mediated aminative cyclization–oxidation reactions. This strategy employs no additives like oxidant, metal catalyst, bases, and represents yet another novel reactivity profile of the building blocks α,α-diiodo-α’-acetoxyketones.
Ruthenium(II)-catalyzed synthesis of 2-arylbenzimidazole and 2-arylbenzothiazole in water
Singh, Keisham S.,Joy, Francis,Devi, Prabha
, p. 181 - 190 (2020/11/26)
Benzimidazoles/benzothiazoles are heterocyclic compounds which contain a five membered heteroatom and a benzene ring. They constitute a crucial structural unit of numerous bioactive compounds and natural products. Since the compounds containing benzimidaz
