73008-33-0Relevant academic research and scientific papers
A Magnetic Heterogeneous Biocatalyst Composed of Immobilized Laccase and 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO) for Green One-Pot Cascade Synthesis of 2-Substituted Benzimidazole and Benzoxazole Derivatives under Mild Reaction Conditions
Mogharabi-Manzari, Mehdi,Kiani, Mahshid,Aryanejad, Sima,Imanparast, Somaye,Amini, Mohsen,Faramarzi, Mohammad Ali
, p. 3563 - 3571 (2018)
The design of reusable high-performance heterogeneous catalysts via the immobilization of chemical and biochemical species on magnetic nanoparticles increases the efficiency of catalytic systems by facilitating easy, fast, and clean separation processes. Laccase and 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl were separately immobilized on amine functionalized iron (II, III) oxide nanoparticles with covalent bonding using glutaraldehyde as a coupling reagent. The prepared catalyst was used to synthesize 12 benzoxazole and benzimidazole derivatives. The one-pot, two-step enzymatic aerobic oxidation reaction included the condensation of in situ-produced salicylaldehyde derivatives with aromatic amines, followed by an enzymatic dehydrogenation process. Optimal reaction conditions consisted of a citrate buffer (10 mM, pH 4.5) at 40 °C for an incubation time of 10 h and a heterogeneous catalyst containing immobilized laccase (80 mg, 100 U) and immobilized 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) (40 mg, 2 mol%). The catalyst retained more than 85% of its initial activity after 10 runs. In addition to the potential for reuse without significant losses in performance, eco-friendly attributes of this catalytic system include its high catalytic activity and the ease with which it can be recovered from the reaction mixture using an external magnet. (Figure presented.).
Near-infrared (NIR) luminescent hetero-tetranuclear Zn2Ln 2 (Ln = Nd, Yb or Er) complexes self-assembled from the benzimidazole-based HL and two rigid 4,4′-bipyridine ligands with different spacers
Zhang, Zhao,Feng, Weixu,Su, Peiyang,Liu, Han,Zhang, Yao,Wang, Zheng,Miao, Tiezheng,Lue, Xingqiang,Fan, Daidi,Wong, Wai-Kwok,Jones, Richard A.
, p. 102 - 110 (2013)
(Chemical Equation Presented) Through the self-assembly of the benzimidazole-based ligand HL (HL = 2-(1H-benzo[d]imidazol-2-yl)-6- methoxyphenol) with Zn(OAc)2·2H2O, Ln(NO 3)3·6H2O (Ln = Nd, Yb, Er or
Exciplex formation between a pair of synthesized AIEgens leads to white light generation: A spectroscopic exploration
Bhattacharyya, Arghyadeep,Guchhait, Nikhil
, p. 10671 - 10680 (2020)
Two compounds, namely 2-(1H-benzo[d]imidazol-2-yl)-6-methoxyphenol (BIMP) and (E)-ethyl 2-cyano-3-(pyren-3-yl)acrylate (ECPA), were synthesized and characterized. BIMP portrayed an interesting feature of aggregation promoted enhancement of excited state intramolecular proton transfer (ESIPT) in water. On the other hand, ECPA shows AIE emission in solution. Steady state spectroscopic studies revealed that the BIMP-ECPA ensemble in solution behaves as a white light emitter, where BIMP acts as a donor and ECPA as an acceptor. The mechanism operative behind the observed white light generation was revealed to be exciplex formation between BIMP and ECPA. The current report is the first example of white light generation from two synthesized AIEgens through exciplex formation and hence holds its own merit for a smart choice of synthesized compounds resulting in white light generation. This journal is
2-(3-Methoxy-2-hydroxyphenyl)benzimidazole
Elerman, Yalcin,Kabak, Mehmet
, p. 372 - 374 (1997)
Molecules of the title compound, 2-(1,3-benzimidazol-2-yl)-6-methoxyphenol, C14H12N2O2, are nearly planar, the greatest deviations from the molecular least-squares plane being -0.145 (3) A for C12 and -0.149 (3) A for C14. An intramolecular O - H...N hydrogen bond [O1...N1 2.577 (6) A] is observed.
Synthesis and fungicidal activity of novel 6H-benzimidazo[1,2-c][1,3]benzoxazin-6-ones
Jiao, Yinchun,Ma, Caixia,Tan, Yuhuan,Tang, Zilong
, p. 581 - 587 (2021/06/16)
[Figure not available: see fulltext.] A series of 6H-benzimidazo[1,2-c][1,3]benzoxazin-6-one derivatives were synthesized in moderate to good yield by reaction of 2-(1H-benzimidazol-2-yl)phenols with triphosgene, and the structures of the target compounds
The ninhydrin core as carbonyl source to access 2-(2′-hydroxyaryl)benzimidazoles exploiting the ortho selectivity of ninhydrin-phenol adducts
Das, Suven,Maity, Suvendu,Ghosh, Prasanta,Dutta, Arpita
, p. 2862 - 2872 (2021/08/13)
Although ninhydrin is an essential analytical tool in biochemical and forensic sciences, for the past several years, it has been employed as efficient building block for diverse organic scaffolds. In the present work, the ortho selectivity of ninhydrin-phenol adducts has been exploited to obtain 2-(2′-hydroxyaryl)benzimidazoles which are well known excited state intramolecular proton transfer (ESIPT) fluorophores. Under acidic condition, 3-(2-hydroxyaroyl)isoindolin-1-one intermediate generated in situ from ninhydrin-phenol adducts was treated with o-phenylenediamine resulting benzimidazole scaffolds via a two-step one pot strategy.
A novel ternary GO@SiO2-HPW nanocomposite as an efficient heterogeneous catalyst for the synthesis of benzazoles in aqueous media
Habibzadeh, Setareh,Firouzzadeh Pasha, Ghasem,Tajbakhsh, Mahmood,Amiri Andi, Nasim,Alaee, Ehsan
, p. 934 - 944 (2019/06/13)
A new solid acid catalyst, consisting of 12-phosphotungstic heteropoly acid (HPW) supported on graphene oxide/silica nanocomposite (GO@SiO2), has been developed via immobilizing HPW onto an amine-functionalized GO/SiO2 surface through coordination interaction (GO@SiO2-HPW). The GO@SiO2-HPW nanocomposite was characterized by Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and powder X-ray diffraction (XRD). The prepared nanocomposite could be dispersed homogeneously in water and further used as a heterogeneous, reusable, and efficient catalyst for the synthesis of benzimidazoles and benzothiazoles by the reaction of 1,2-phenelynediamine or 2-aminothiophenol with different aldehydes.
Experimental and theoretical approving of anomeric based oxidation in the preparation of 2-sbstituted benz-(imida, oxa and othia)-zoles using [2,6-DMPy-NO2]C(NO2)3 as a novel nano molten salt catalyst
Zolfigol, Mohammad Ali,Khazaei, Ardeshir,Alaie, Saied,Baghery, Saeed,Maleki, Farahnaz,Bayat, Yadollah,Asgari, Asiye
, p. 58667 - 58679 (2016/07/06)
The synthesis of 2-sbstituted benz-(imida, oxa and othia)-zole derivatives were occurred in the presence of 2,6-dimethyl-1-nitropyridin-1-ium trinitromethanide [2,6-DMPy-NO2]C(NO2)3via the condensation reaction between 1,2-phenylenediamine or 2-aminophenol or 2-aminothiophenol and corresponding aldehyde at room temperature under solvent-free conditions respectively. [2,6-DMPy-NO2]C(NO2)3 as a nano molten salt (NMS) catalyst was fully characterized by Fourier transform infrared (FT-IR), nuclear magnetic resonance (1H NMR and 13C NMR), mass, thermal gravimetric (TG), derivative thermal gravimetric (DTG), X-ray diffraction patterns (XRD), scanning electron microscopy (SEM) and transmission electron microscopy (TEM) analysis. The described reactions are in close agreement with the green chemistry disciplines and their major advantages are good yields, short reaction time and ease of separation. Our recently new introduced concept entitled "anomeric based oxidation" was proposed for the final step of the described synthesis and it was also approved using theoretical studies.
Benzimidazoles: A new class of carbonic anhydrase inhibitors
Khan, Khalid Mohammed,Khan, Momin,Saleem, Muhammad,Taha, Muhammad,Perveen, Shahnaz,Choudhary, Mohammad Iqbal
, p. 901 - 904 (2013/07/26)
Carbonic anhydrase inhibitory activity of benzimidazole derivatives 1-24 has been evaluated. Compounds 22 (IC50 = 7.47 ± 0.39 μM), 21 (IC50 = 10.31 ± 0.11 μM), 20 (IC50 = 23.1 ± 1.78 μM), 12 (IC50 = 12.16 ± 0.10
One-pot synthesis of benzimidazoles and benzothiazoles in the presence of Fe(HSO4)3 as a new and efficient oxidant
Eshghi, Hossein,Rahimizadeh, Mohammad,Shiri, Ali,Sedaghat, Parisa
experimental part, p. 515 - 518 (2012/04/23)
A series of substituted benzimidazoles and benzothiazoles were prepared through the one-pot reaction of ophenylenediamine and o-aminothiophenol with various aldehydes in the presence of ferric hydrogensulfate both in EtOH and water as solvent. The reactions proceed smoothly in excellent yield, high chemoselectivity and with an easy work-up.
