- Exploring beta amyloid cleavage enzyme-1 inhibition and neuroprotective role of benzimidazole analogues as anti-alzheimer agents
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Beta amyloid cleavage enzyme-1 (BACE1) is the key enzyme involved in Aβ peptide formation in Alzheimer's disease pathogenesis. We intend to target this enzyme by exploring benzimidazole analogues against BACE1 as potential anti-Alzheimer agents. Docking studies were performed to determine the hydrogen bond interactions between the designed molecules and the target protein's active site. Research indicates the relationship between oxidative stress and Aβ effect in precipitating neurodegeneration; hence, the series was also studied in vitro to ascertain its neuroprotective role by performing the lipid peroxidation assay. In silico absorption, distribution, metabolism, and excretion studies were undertaken to assess the drug-like suitability of the analogues. To judge the effect of the synthesized analogues on central nervous system (CNS), toxicity and memory model studies were conducted on mice. Thus, overall results showcase analogues 11 and 14 as the most promising ones with the dual role of BACE1 inhibition and neuroprotection, along with memory retention.
- Gurjar, Archana S.,Solanki, Vivek S.,Meshram, Ankita R.,Vishwakarma, Suchita S.
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- Green synthesis of benzimidazole derivatives under ultrasound irradiation using Cu-Schiff base complexes embedded over MCM-41 as efficient and reusable catalysts
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We have synthesized two recoverable catalysts by covalently attaching complexes such as Cu-complex-phen and Cu-complex-bipy on MCM-41 through a greener synthetic route. FT-IR, EDX, SEM and TEM microscopy, XRD analysis, N2 adsorption and desorpt
- Bharathi, M.,Indira, S.,Induja, E.,Mahalakshmi, T.,Shamuga Bharathi, K.,Vinoth, G.
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- Reevaluating the synthesis of 2,5-disubstituted-1H-benzimidazole derivatives by different green activation techniques and their biological activity as antifungal and antimicrobial inhibitor
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A comparative study concerned with the preparation of diversely substituted-1H-benzimidazole under different green activation techniques and conventional methods is reported. Data are collected for infrared, ultrasound, microwave, and simultaneous irradiation with US and IR sources, as this last strategy shows an important improvement. Further, the small library of potentially bioactive benzimidazole 17-76 synthesized was screened as an antifungal and antimicrobial agent. Strong activity against Candida albicans and Staphylococcus aureus was observed. Remarkably, 2-(4-aminophenyl)-5-phenylamino-1H-benzimidazole 63 resulted better than that of reference drugs miconazole with a zone of inhibition up to 42 mm. Likewise, 2-(2-aminophenyl)-1H-benzimidazole 21 showed substantial antimicrobial activity against MRSA strain. When assayed by the microdilution method, this azaheterocyclic compound presented a minimum inhibitory concentration (MIC) ≥ 16.4 μg/100 mL and a bacterial percentage reduction of 96%.
- Penieres-Carrillo, José-Guillermo,Ríos-Guerra, Hulme,Pérez-Flores, Javier,Rodríguez-Molina, Braulio,Torres-Reyes, ángeles,Barrera-Téllez, Francisco,González-Carrillo, Jessica,Moreno-González, Lessly,Martínez-Zaldívar, Alejandro,Nolasco-Fidencio, Juan-Jesús,Matus-Meza, Audifás-Salvador,Luna-Mora, Ricardo-Alfredo
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- Facile and selective synthesis of 2-substituted benzimidazoles catalyzed by FeCl3/Al2O3
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2-Substituted benzimidazoles were synthesized in a single pot from aromatic aldehydes and o-phenylenediamine catalyzed by FeCl3/Al 2O3 in DMF at ambient temperature attained good yields and high selectivity.
- Chen, Guo-Feng,Dong, Xiao-Yun
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- Single Heteroatom Fine-Tuning of the Emissive Properties in Organoboron Complexes with 7-(Azaheteroaryl)indole Systems
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The application of organoboron compounds as light-absorbing or light-emitting species in areas as relevant as organic electronics or biomedicine has motivated the search for new materials which contribute to the progress of those applications. This articl
- Más-Montoya, Miriam,Usea, Laura,Espinosa Ferao, Arturo,Montenegro, María F.,Ramírez De Arellano, Carmen,Tárraga, Alberto,Rodríguez-López, José N.,Curiel, David
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- [Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)]: Synthesis, crystal structure, catalytic activity and DFT study
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Metal-organic hybrid complexes often exhibit large surface area, pore volume, fascinating structures and potential applications including catalytic applications. Hence a new metal-organic hybrid complex [Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)] was synthesized using conventional method. Physico-chemical characterization of the complex was performed with FTIR spectroscopy, single crystal X-ray diffraction, TGA, EPR and FESEM. Single crystal X-ray diffraction study suggests it to be three dimensional with space group P212121 (orthorhombic). The crystal achieves its three-dimensional structure and stability through extensive intermolecular hydrogen bonding. Hirshfeld surface analysis, catalytic activity and DFT study of the complex was also performed. The synthesized complex acts as good catalyst in benzimidazole synthesis with good recyclability as catalyst up to 5th run.
- Brahman, Dhiraj,Chhetri, Sailesh,Kamath, Amarjit,McArdle, Patrick,Sinha, Biswajit
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- 1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles
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In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]
- Kalhor, Mehdi,Zarnegar, Zohre
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p. 519 - 540
(2021/12/03)
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- Application of sulfonic acid fabricated cobalt ferrite nanoparticles as effective magnetic nanocatalyst for green and facile synthesis of benzimidazoles
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This work represents the design and synthesis of efficient sulfonated cobalt ferrite solid acid catalyst. The synthesized solid acid green catalyst was characterized using various techniques viz. FT-IR, powder XRD, SEM, TEM and VSM. The obtained catalyst was used to synthesize biologically significant 2-substituted benzimidazole derivatives by condensation between o-phenylenediamine with various aromatic, aliphatic and heterocyclic aldehydes. High yield (up to 98 %), short reaction time (10?25 min), mild reaction condition, wide functional group tolerance, easy work-up procedure and excellent values of green chemistry metrices such as lower E factor (0.126), high RME value (88.83 %), carbon efficiency (100 %) and high atom economy (AE) value (90.65 %), are some salient features of the present catalytic system. Moreover, the catalyst recovery by simply using an external magnet and catalyst reusability up to 7 times without any significant loss in catalytic efficiency are some additional remarkable features of the current protocol.
- Yadav, Priyanka,Kakati, Praachi,Singh, Preeti,Awasthi, Satish K.
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- Syntheses, characterization, and catalytic potential of novel vanadium and molybdenum Schiff base complexes for the preparation of benzimidazoles, benzoxazoles, and benzothiazoles under thermal and ultrasonic conditions
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A new ONO-tridentate Schiff base ligand (H2L) derived from 3-methoxysalicylaldehyde and nicotinic hydrazide was synthesized and characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, UV–Vis, and powder XRD studies. Then, oxovanadium(V) and dioxomolybdenum(VI) Schiff base complexes, VOL and MoO2L, were also prepared and characterized by different techniques. Moreover, the catalytic activities of both complexes were investigated for the synthesis of benzimidazoles, benzoxazoles, and benzothiazoles under reflux conditions as well as through ultrasonic irradiation. The results revealed several advantages of this procedure, including high product yields, short reaction times, facile work-up procedure, simplicity in operation, eco-friendly reaction conditions, and green aspects by avoiding toxic catalysts and solvents. Graphic abstract: [Figure not available: see fulltext.]
- Kargar, Hadi,Kargar, Khadijeh,Fallah-Mehrjardi, Mehdi,Munawar, Khurram Shahzad
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p. 593 - 605
(2021/06/21)
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- Water extract of onion catalyst: An economical green route for the synthesis of 2-substituted and 1,2-disubstituted benzimidazole derivatives with high selectivity
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An efficient, environmental friendly and substrate controlled method of synthesis of 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 with high selectivity has been achieved from the reaction of o-phenylenediamine 1 and aldehydes 2 in the presence of water extract of onion and selecting suitable reaction medium. This method is widely applicable for variety of aldehydes such as aromatic/aliphatic/heterocyclic aldehydes and 1,2-diamines to afford 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 in good to excellent yields (up to 96%). The developed method of water extract of onion catalysis produced 2-substituted benzimidazoles 3 from aromatic aldehydes having electron-withdrawing groups, whereas aromatic aldehydes bearing electron donating groups selectively furnished 1,2-disubstituted benzimidazole 4 derivatives. The process described here has several advantages of cheap, low energy consumption, commercially available starting materials, operational simplicity and nontoxic catalyst. The use of water extract of onion makes this present methodology green and giving a useful contribution to the existing methods available for the preparation of benzimidazole derivatives. In addition, Hammett correlation of substituent constant (σ) vs percentage (%) yield has been established.
- Kaliyan, Prabakaran,Selvaraj, Loganathan,Muthu, Seenivasa Perumal
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supporting information
p. 340 - 349
(2020/12/01)
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- N-Alkylation of 2-Substituted Benzimidazole Derivatives and Their Evaluation as Antinemic Agents
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Abstract: 2-Substituted benzimidazole derivatives were synthesized by condensation ofo-phenylenediamine with the correspondingsubstituted benzaldehydes and were alkylated at the nitrogen atom usingC3–C10 alkyl bromides in thepresence
- Dhillon, N. K.,Kaur, L.,Utreja, D.
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p. 961 - 967
(2021/08/09)
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- TEMPO supported amine functionalized magnetic titania: a magnetically recyclable catalyst for the aerobic oxidative synthesis of heterocyclic compounds
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Abstract: The present protocol uncover a new strategy to synthesize highly efficient solid TEMPO based catalyst in which 4-oxo-TEMPO was covalently tethered to the surface of amine functionalized magnetic titania. The chemical nature and structure of the
- Sharma, Sukanya,Choudhary, Anu,Sharma, Shally,Shamim, Tahira,Paul, Satya
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- A Novel Synthesis of 2-Arylbenzimidazole and 2-Arylbenzothiazole Derivatives by MnO2/MOF-199
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The main objective of this research is to develop efficient and environmentally benign heterogeneous catalysts for synthesis of 2-arylbenzimidazole and 2-arylbenzothiazoles derivatives by MnO2/MOF-199. For this purpose, a heterogeneous MnO2/MOF-199 catalyst was prepared by the solvothermal method, and the prepared catalyst was characterised by various techniques such as X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), BET, IR, thermogravimetric-differential thermogravimetric (TG-DTG), and temperature-programmed desorption with ammonia (NH3-TPD) analysis. The solid catalyst, with a MnO2/MOF-199 loading of 9 %, demonstrated a high catalytic activity in the synthesis of 1,2-arylbenzimidazole and 1,2-arylbenzothiazole derivatives and the catalyst could be reused for at least 5 cycles under mild conditions.
- Amouhadi, Elham,Fazaeli, Razieh,Aliyan, Hamid
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p. 495 - 502
(2021/02/09)
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- Highly Potent and Selective Butyrylcholinesterase Inhibitors for Cognitive Improvement and Neuroprotection
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Butyrylcholinesterase (BChE) has been considered as a potential therapeutic target for Alzheimer's disease (AD) because of its compensation capacity to hydrolyze acetylcholine (ACh) and its close association with Aβ deposit. Here, we identified S06-1011 (hBChE IC50 = 16 nM) and S06-1031 (hBChE IC50 = 25 nM) as highly effective and selective BChE inhibitors, which were proved to be safe and long-acting. Candidate compounds exhibited neuroprotective effects and the ability to improve cognition in scopolamine- and Aβ1-42 peptide-induced cognitive deficit models. The best candidate S06-1011 increased the level of ghrelin, a substrate of BChE, which can function as improving the mental mood appetite. The weight gain of the S06-1011-treated group remarkably increased. Hence, BChE inhibition not only plays a protective role against dementia but also exerts a great effect on treating and nursing care.
- Li, Qi,Chen, Ying,Xing, Shuaishuai,Liao, Qinghong,Xiong, Baichen,Wang, Yuanyuan,Lu, Weixuan,He, Siyu,Feng, Feng,Liu, Wenyuan,Chen, Yao,Sun, Haopeng
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p. 6856 - 6876
(2021/05/29)
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- UV-visible light-induced photochemical synthesis of benzimidazoles by coomassie brilliant blue coated on W-ZnO@NH2nanoparticles
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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.
- Chen, Ruijuan,Jalili, Zahra,Tayebee, Reza
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p. 16359 - 16375
(2021/05/19)
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- Cu-Mn Bimetallic Complex Immobilized on Magnetic NPs as an Efficient Catalyst for Domino One-Pot Preparation of Benzimidazole and Biginelli Reactions from Alcohols
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An efficient magnetically recyclable bimetallic catalyst by anchoring copper and manganese complexes on the Fe3O4 NPs was prepared and named as Fe3O4@Cu-Mn. It was founded as a powerful catalyst for the domino one-pot oxidative benzimidazole and Biginelli reactions from benzyl alcohols as a green protocol in the presence of air, under solvent-free and mild conditions. Fe3O4@Cu-Mn NPs were well characterized by FT-IR, XRD, FE-SEM, TEM, VSM, TGA, EDX, DLS, and ICP analyses. The optimum range of parameters such as time, temperature, amount of catalyst, and solvent were investigated for the domino one-pot benzimidazole and Biginelli reactions to find the optimum reaction conditions. The catalyst was compatible with a variety of benzyl alcohols, which provides favorable products with good to high yields for all of derivatives. Hot filtration and Hg poisoning tests from the nanocatalyst revealed the stability, low metal leaching and heterogeneous nature of the catalyst. To prove the synergistic and cooperative effect of the catalytic system, the various homologues of the catalyst were prepared and then applied to a model reaction separately. Finally, the catalyst could be filtered from the reaction mixture simply, and reused for five consecutive cycles with a minimum loss in catalytic activity and performance. Graphic Abstract: A new magnetically recyclable Cu/Mn bimetallic catalyst has been developed for domino one-pot oxidation-condensation of benzimidazole and Biginelli reactions from alcohols. [Figure not available: see fulltext.]
- Nasseri, Mohammad Ali,Rezazadeh, Zinat,Kazemnejadi, Milad,Allahresani, Ali
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p. 1049 - 1067
(2020/09/11)
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- Synthesis of benzimidazoles by two methods (C–H functionalization and condensation reaction) catalyzed by α-zirconium hydrogen phosphate-based nanocatalyst
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In this report, two heterogeneous nanocatalysts based on α-zirconium hydrogen phosphate were applied. These heterogeneous catalysts have demonstrated the promising catalytic activity for the synthesis of 2-substituted benzimidazoles in two different methods. One of these reactions is the functionalization of the C–H bond and the formation of C–N bond, and the other reaction involves the condensation reaction between aldehydes and 1,2-phenylenediamine. The activity of both catalysts was compared in two methods, and the superior catalyst was introduced. The prepared catalysts are easily separated from the reaction mixture by centrifugation and reused several times without significant loss of activity.
- Hajipour, Abdol R.,Zakery, Saedeh,Khorsandi, Zahra
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p. 1919 - 1931
(2020/05/28)
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- Amide-imine conjugate involving gallic acid and naphthalene for nano-molar detection, enrichment and cancer cell imaging of La3+: Studies on the catalytic activity of the La3+complex
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A single crystal X-ray structurally characterized amide-imine conjugate (GAN) derived from gallic acid and naphthalene selectively recognizes La3+ ions via TURN ON fluorescence through ESIPT and CHEF mechanisms. GAN can detect as low as 23.93 × 10-9 M La3+ ions and image intracellular La3+ ions in live HeLa and SiHa cells under a fluorescence microscope in a time- and concentration dependent manner. The corresponding [La(iii)-GAN] complex is established as an efficient catalyst for the synthesis of benzimidazole derivatives from o-phenylenediamine and substituted benzaldehydes. Moreover, GAN is very useful for enrichment of La3+ in ethyl acetate medium. This journal is
- Shaikh, Ahad,Ghosh, Milan,Mukherjee, Pallabi,Ghosh, Avijit,Molla, Rostam Ali,Ta, Sabyasachi,Das, Debasis
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supporting information
p. 13501 - 13506
(2020/08/28)
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- A facile and efficient synthesis of benzimidazole as potential anticancer agents
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Abstract: This study reports a simple process to synthesize and separate of 2-(substituted-phenyl) benzimidazole derivatives with high yield and efficiency. Specifically, by reacting ortho-phenylenediamines with benzaldehydes using sodium metabisulphite a
- Hoang, Thi-Kim-Dung,Huynh, Thi-Kim-Chi,Nguyen, Thanh-Danh,Nguyen, Thi-Hong-An,Tran, Ngoc-Hoang-Son
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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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- Catalytic activity of Co(II) Salen&at;KCC-1 on the synthesis of 2,4,5-triphenyl-1H-imidazoles and benzimidazoles
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The synthesis, reactions and biological properties of imidazoles and benzimidazole make up the bulk of the ring chemistry. In this study, the reaction between different types of aromatic aldehydes and ammonium acetate with diphenylethanedione, in ethanol solvent, using the Co(II) Salen complex&at;KCC-1 catalyst which is produced from Co (II) complex which is supported onto the KCC-1 was studied. The results showed that the products were synthesized in good to excellent yields. The products were identified with IR and NMR spectroscopy. Also, the catalyst was identified by FT-IR, TGA, TEM, and XRD. Finally, the catalyst was reused several times without lack of catalytic activity.
- Ali Nasseri, Mohammad,Allahresani, Ali,Naghdi, Elaheh
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- Hypervalent iodine promoted: Ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates
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The mild and efficient palladium-catalyzed ortho C(sp2)-H diversification of (NH)-free 2-substituted benzimidazole, quinazoline, and imidazopyridine is reported using hypervalent iodine as the key reagent. Acetoxy, aryl, iodide and nitro functi
- Saha, Moumita,Das, Asish R.
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supporting information
p. 941 - 955
(2020/02/15)
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- Selective photocatalytic oxidation of aromatic alcohols to aldehydes with air by magnetic WO3ZnO/Fe3O4.: In situ photochemical synthesis of 2-substituted benzimidazoles
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Recently, visible light-driven organic photochemical synthesis has been a pioneering field of interest from academic and industrial associations due to its unique features of green and sustainable chemistry. Herein, WO3ZnO/Fe3O4 was synthesized, characterized, and used as an efficient magnetic photocatalyst in the preparation of a range of 2-substituted benzimidazoles via the condensation of benzyl alcohol and o-phenylenediamine in ethanol at room temperature for the first time. The key feature of this work is focused on the in situ photocatalytic oxidation of benzyl alcohols to benzaldehydes under atmospheric air and in the absence of any further oxidant. This new heterogeneous nanophotocatalyst was characterized via XRD, FT-IR, VSM and SEM. Short reaction time, cost-effectiveness, broad substrate scope, easy work-up by an external magnet, and excellent product yield are the major advantages of the present methodology. A number of effective experimental parameters were also fully investigated to clear broadness and generality of the protocol. This journal is
- Esmaeili, Effat,Li, Bozhi,Maleki, Behrooz,Namaghi, Mina S.,Tayebee, Reza
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p. 40725 - 40738
(2020/11/23)
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- Microwave use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds method
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The invention discloses a microwave the use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds, in the aqueous phase under microwave conditions adding benzoic amidine compound under alkaline condition [...] into benzimidazole reaction, invention an environment-friendly, the operation is simple, cheap and safe, efficient process for preparing benzimidazole method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection; .
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Paragraph 0043
(2019/03/28)
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- Aerobic {Mo72V30} nanocluster-catalysed heterogeneous one-pot tandem synthesis of benzimidazoles
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A novel heterogeneous one-pot protocol is developed for tandem aerobic synthesis of benzimidazoles through dehydrogenative coupling of primary benzylic alcohols and aromatic diamines co-catalysed by Keplerate-type {Mo72V30} polyoxometalate and N-hydroxyphthalimide (NHPI). The catalytic system also works well for the synthesis of benzimidazoles using benzaldehydes, as commonly used starting materials, in the absence of NHPI. The high activity of the solid nanocluster provides standard conditions avoiding current limitations of oxidation methods including high catalyst loadings. The spectral results and leaching experiments revealed that the nanocapsule preserved its structural integrity after being reused in consecutive runs.
- Khoshyan, Ashkan,Pourtahmasb, Mehrdad,Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
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- Synthesis of new TCH/Ni-based nanocomposite supported on SBA-15 and its catalytic application for preparation of benzimidazole and perimidine derivatives
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A stable nickel-decorated SBA-15 nanocomposite (Ni/TCH@SBA-15) was synthesized through surface modification of silica nanoparticles with 3-chloropropyltriethoxysilane (CPTES) and thiocarbohydrazide (TCH) followed by metal–ligand coordination with Ni (II). The structure of this organometallic nanocomposite was characterized by Fourier transform-infrared, field emission-scanning electron microscopy, EDAX, transmission electron microscopy, atomic absorption spectroscopy and N2 adsorption–desorption (Brunauer–Emmett–Teller) techniques. The catalytic performance of Ni/TCH@SBA-15 (NNTS-15) was determined for the synthesis of 2-aryl-substituted benzimidazoles and 2,3-dihydroperimidines. The excellent yields within shorter reaction times, simplicity of catalytic methods, non-toxicity and clean reactions, mild reaction conditions and easy work-up procedure are the important merits of these synthetic protocols. Moreover, the Ni (II) bonded to the SBA-15 surface was stable under the catalytic reaction conditions resulting in its efficient recycling and reuse.
- Kalhor, Mehdi,Rezaee-Baroonaghi, Fahimeh,Dadras, Akbar,Zarnegar, Zohre
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- A nanoscopic icosahedral {Mo72Fe30} cluster catalyzes the aerobic synthesis of benzimidazoles
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In this study, the catalytic efficiency of amorphous {Mo72Fe30} nanocapsules as a safe Keplerate polyoxometalate in organic synthesis was exploited. The easy-made solid catalyst exhibited high efficiency using a very low dosage (0.02
- Garazhian, Zohreh,Rezaeifard, Abdolreza,Jafarpour, Maasoumeh
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p. 34854 - 34861
(2019/11/14)
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- Organocatalytic Green Approach Towards the Fabrication of Fused Benzo N,N-containing Heterocycles Facilitated by Ultrasonic Irradiation
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The development of a metal-free protocol for transformations in organic synthesis offers a significant potential environmental benefit. This article reports the exploration of meglumine, a nontoxic and biodegradable amino sugar, as an organocatalyst for the synthesis of biologically active 1H-dibenzo[b,e][1,4]diazepin-1-ones, highly regioselective benzimidazole derivatives and derivatives of quinoxalines. Operational simplicity, mild reaction conditions, shorter reaction times, and use of green solvents are the highlights of this protocol. The advantage of ultrasonic irradiation has been significantly explored for the synthesis of the aforesaid compounds. Furthermore, the multifaceted use of o-phenylenediamine has also been accentuated in the study.
- Nongrum, Ridaphun,Kharmawlong, George Kupar,Rani, Jims World Star,Rahman, Noimur,Dutta, Arup,Nongkhlaw, Rishanlang
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- Design, synthesis, antifungal activity and 3D-QSAR study of novel pyrazole carboxamide and niacinamide derivatives containing benzimidazole moiety
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A series of novel pyrazole carboxamide and niacinamide derivatives containing a benzimidazole moiety were designed and synthesized as antifungal candidate agents. All target compounds were characterized by FTIR, 1H NMR, 13C NMR, HRMS and elemental analysis techniques. The structure of compound T1 was further confirmed by single crystal X-ray diffraction analysis. The antifungal activities of the target compounds were evaluated in vitro against four phytopathogenic fungi (namely Botrytis cinerea, Rhizoctonia solani, Fusarium graminearum and Alternaria solani) by the mycelium growth inhibition method. The bioassay results indicated that some of the compounds exhibited good antifungal activity against B. cinerea at 100 μg ML?1 compared to other three fungi. In order to better explore the structure-activity relationship (SAR), the EC50 values of target compounds against B. cinerea were measured and assessed. Subsequently, a 3D quantitative structure-activity relationship (3D-QSAR) study was carried out using the comparative molecular field analysis (CoMFA) technique based on the inhibitory activities of tested compounds against B. cinerea. Molecular modelling results revealed fine predictive ability with cross-validated q2 and non-cross-validated r2 values of 0.578 and 0.850, respectively.
- Si, Wei-Jie,Wang, Xiao-Bin,Chen, Min,Wang, Meng-Qi,Lu, Ai-Min,Yang, Chun-Long
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p. 3000 - 3010
(2019/02/17)
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- Synthesis and characterization of a new poly(N–heterocyclic carbene Cu complex) immobilized on nano–silica, (CuII–NHCs)n@nSiO2, and its application as an efficient and reusable catalyst in the synthesis of benzimidazoles,
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The present study describes the synthesis and characterization of a new poly(N–heterocyclic carbene Cu complex) immobilized on nano silica, (CuII–NHCs)n@nSiO2. The (CuII–NHCs)n@nSiO2 dendri
- Khajehzadeh, Mostafa,Moghadam, Majid,Jamehbozorgi, Saeed
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p. 173 - 189
(2018/10/21)
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- Synthesis, antimicrobial evaluation and molecular docking of some potential 2,6-disubstituted 1h-benzimidazoles; non-classical antifolates
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Background: Dihydrofolate reductase is one of the important enzymes for thymidylate and purine synthesis in micro-organisms. A large number of drugs have been designed to inhibit microbial DHFR but over the period of time, some drugs have developed resist
- Harer, Sunil,Bhatia, Manish,Kawade, Vikram
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p. 813 - 832
(2019/11/02)
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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; 0032
(2018/11/27)
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- Synthesis of graphene oxide supported copper–cobalt ferrite material functionalized by arginine amino acid as a new high–performance catalyst
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A novel Cu0.5Co0.5Fe2O4@Arg–GO catalytic system was successfully prepared by immobilization of copper substituted cobalt ferrite nanoparticles on arginine–grafted graphene oxide nanosheets, in which ferrite moiety acts as an oxidation catalyst and arginine has the role of base catalyst. Also, arginine amino acid was used to modify the surface of graphene oxide nanosheets which the prepared support can improve dispersion and uniform loading of nanoparticles. The prepared nanocomposite was characterized by flame atomic absorption spectroscopy (FAAS), inductively coupled plasma optical emission spectrometer (ICP–OES), energy dispersive spectroscopy (EDS), Fourier transform infrared spectroscopy (FT–IR), ultraviolet–visible spectroscopy (UV–vis), Raman spectroscopy, thermogravimetric analysis (TGA), x–ray diffraction (XRD), scanning electron microscopy (SEM), and transmission electron microscopy (TEM) analysis. The prepared Cu0.5Co0.5Fe2O4@Arg–GO nanocomposite was used as an efficient catalyst for one–pot tandem oxidative synthesis of 2–phenylbenzimidazole derivatives in good yields.
- Ghadari, Rahim,Namazi, Hassan,Aghazadeh, Mohammad
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- Preparation of 2-Arylbenzimidazole derivatives using CuO nanoparticles /H2O2 system
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CuO nanoparticles were prepared in watery lemon juice media and were characterized by XRD, FE-SEM, DLS, TGA and BET analysis. The as-prepared catalyst was efficient and recyclable for a high yielding, and practical method for the synthesis of 2-arylbenzimidazoles via cyclo-condensation reaction of 1,2-benzenediamine and aldehydes using copper oxide (CuO) nanoparticles is reported. Solvents and solvent-free effects on the reaction were investigated. Solvent plays a significant role in the reaction, and best results were achieved in solvent-free condition at 80°C. All reactions were completed in short reaction times (20–120?min) with 76–97% yields.
- Fazlinia, Abbas,Sheikh, Setareh
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p. 126 - 130
(2018/02/06)
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- A modern and practical laccase-catalysed route suitable for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
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Heterocyclic aromatic compounds containing an imine (C═N) bond such as benzimidazoles and benzothiazoles are important active pharmaceutical ingredients. The synthesis of 2-aryl-1H-benzimidazoles and 2-arylbenzothiazoles in good to excellent yields was ac
- Maphupha, Mudzuli,Juma, Wanyama P.,De Koning, Charles B.,Brady, Dean
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p. 39496 - 39510
(2018/12/13)
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- A Tandem Aerobic Photocatalytic Synthesis of Benzimidazoles by Cobalt Ascorbic Acid Complex Coated on TiO2 Nanoparticles Under Visible Light
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Abstract: In this study, we developed methods for the one pot environmentally benign synthesis of benzimidazoles by cobalt ascorbic acid complex coated on TiO2 nanoparticles via aerobic photooxidative cyclization reactions. Easy work-up procedure, reusability of the catalyst and scalable to the multi-mole scale, which is valuable for an industrial process make these catalytic systems highly attractive. Also, the combination of photocatalytic and catalytic reactions presented here may help to develop a new strategy towards the development of photocatalysis-based organic synthesis. Graphical Abstract: [Figure not available: see fulltext.].
- Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
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- One-pot, green approach synthesis of 2-aryl substituted benzimidazole derivatives catalyzed by water extract of papaya bark ash
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A simple, green, rapid and environmentally benign route has been developed for the synthesis of 2-substituted benzimidazoles by the reaction of substituted o-phenylenediamine with different substituted benzoyl chloride using water extract of papaya bark ash (WEPBA) as a green catalyst at room temperature. This method provides several added advantages of being completely green, economic, giving high yields and minimizing use of hazardous solvents. Further, the separated product does not required any kind of chromatographic purification.
- Kantharaju,Hiremath, Prashant B.
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p. 1634 - 1638
(2018/06/12)
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- Synthesis of 2-aryl-1H-benzimidazoles and 2-aryl-1H-perimidines using arylidene Meldrum’s acid as a source of the aryl group and oxidant
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Arylidene Meldrum’s acid is employed as a source of the aryl group and oxidant for the synthesis of 2-aryl-1H–benzimidazoles by a condensation reaction with 1,2-phenylenediamine in refluxing ethanol with good to high yields. Arylidene Meldrum’s acids were
- Mehrabi, Hossein,Najafian-Ashrafi, Faezeh,Esfandiarpour, Zeinab,Ranjbar-Karimi, Reza
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p. 125 - 128
(2018/04/20)
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- Facile and efficient aerobic one-pot synthesis of benzimidazoles using Ce(NO3)3·6H2O as promoter
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A series of 2-substituted benzimidazoles was synthesized under aerobic conditions, by simply heating 1,2-diaminobenzene and aldehydes in DMF at 80 °C, employing Ce(NO3)3·6H2O as promoter and atmospheric air as an efficient oxidant. The procedure afforded the products from good to excellent yields. Furthermore, this new economic and eco-friendly protocol avoids the use of toxic metal catalysts, as well as additional bases and oxidants.
- Martins, Guilherme M.,Puccinelli, Thiago,Gariani, Rogério A.,Xavier, Fernando R.,Silveira, Claudio C.,Mendes, Samuel R.
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supporting information
p. 1969 - 1972
(2017/04/27)
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- In water–ultrasound-promoted synthesis of tetraketones and 2-substituted-1H-benzimidazoles catalyzed by BiOCl nanoparticles
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A highly efficient, green protocol has been developed for the synthesis of various structurally diverse 2,2′-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 2-substituted-1H-benzimidazole derivatives. The reaction was performed in water under ultrasound irradiation, using BiOCl nanoparticles as a catalyst. The nanocatalyst was found to be reusable for seven subsequent reactions without much loss in activity. Simple methodology with short reaction times and mild reaction conditions with easy work-up procedure are the salient features of this method.
- Sapkal, Bharatkumar M.,Labhane, Prakash K.,Satam, Jitendra R.
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p. 4967 - 4979
(2017/07/22)
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- Efficient preparation of acidic ionic liquid-functionalized reduced graphene oxide and its catalytic performance in synthesis of benzimidazole derivatives
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Abstract: This article reports an efficient method with a simple workup for the facile synthesis of benzimidazole derivatives using an acidic ionic liquid covalently supported on graphene sheets. The catalyst was efficiently synthesized and characterized
- Hanoon,Kowsari,Abdouss,Zandi,Ghasemi
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p. 1751 - 1766
(2017/02/15)
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- Direct conversion of alkyl halides into benzimidazoles using pyridine-N-oxide and 1,2-diaminobenzenes
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Benzimidazole heterocycles were obtained from halogenated compounds and aromatic 1,2-diamines. A mild oxidizing reagent such as pyridine N-oxide (PyO) is required to produce the benzimidazole core. The method is solvent free and provides products without the need for chromatography. Good yields, moderate reaction temperature, fast reaction rates are important advantages of this procedure. {figure presented}.
- Bratulescu, George
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- Nickel-substituted cobalt ferrite nanoparticles supported on arginine-modified graphene oxide nanosheets: Synthesis and catalytic activity
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The amino acid arginine was used to modify the surface of graphene oxide nanosheets and then nickel-substituted cobalt ferrite nanoparticles were supported on those arginine-grafted graphene oxide nanosheets (Ni0.5Co0.5Fe2O4@Arg–GO). The prepared Ni0.5Co0.5Fe2O4@Arg–GO was characterized using flame atomic absorption spectroscopy, inductively coupled plasma optical emission spectrometry, energy-dispersive spectroscopy, Fourier transform infrared spectroscopy, ultraviolet–visible spectroscopy, Raman spectroscopy, X-ray diffraction, thermogravimetric analysis, scanning electron microscopy and transmission electron microscopy. The application of Ni0.5Co0.5Fe2O4@Arg–GO as a catalyst was examined in a one-pot tandem oxidative cyclization of primary alcohols with o-phenylenediamine to benzimidazoles under aerobic oxidation conditions. The results showed that 2-phenylbenzimidazole derivatives were successfully achieved using Ni0.5Co0.5Fe2O4@Arg–GO nanocomposite catalyst via the one-pot tandem oxidative cyclization strategy.
- Ghadari, Rahim,Namazi, Hassan,Aghazadeh, Mohammad
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- Isocyanurate-based periodic mesoporous organosilica (PMO-ICS): A highly efficient and recoverable nanocatalyst for the one-pot synthesis of substituted imidazoles and benzimidazoles
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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.
- Dekamin, Mohammad G.,Arefi, Elham,Yaghoubi, Amene
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p. 86982 - 86988
(2016/10/19)
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- 1,3,5-Trimethylpyrazolium chloride based ionogel as an efficient and reusable heterogeneous catalyst for the synthesis of benzimidazoles
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A new approach for the synthesis of benzimidazoles using ionogel under solvent-free conditions is reported. Catalytic activity of ionogel was compared with silica coated with ionic liquid (silica-IL) and it was found that ionogel is highly active compared to silica-IL for the synthesis of benzimidazoles. Moreover, ionogel was recyclable for the synthesis of benzimidazoles. [Figure not available: see fulltext.]
- Sharma, Pankaj,Gupta, Monika
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- Nano-Ni(II)/Y Zeolite Catalyzed Synthesis of 2-Aryl- and 2-Alkyl Benzimidazoles Under Solvent-Free Conditions
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Synthesis of some benzimidazole derivatives via condensation reaction of o-phenylenediamine derivatives with aromatic aldehydes or orthoesters under solvent-free conditions over nano-Ni(II)/Y zeolite as a heterogeneous catalyst is reported. Some advantages of this green method are easy purification, environmentally friendly conditions, low catalyst loadings, and nontoxic nature.
- Mobinikhaledi,Zendehdel,Goudarzi,Bardajee, G. Rezanejade
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p. 1526 - 1531
(2016/06/09)
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- Catalytic Performance of Hydrophobic Sulfonated Nanocatalysts CMK-5-SO3H and SBA-15-Ph-PrSO3H for Ecofriendly Synthesis of 2-Substituted Benzimidazoles in Water
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The hydrophobicity of environmentally benign organosulfonic acid-functionalized silica (SBA-15-Ph-PrSO3H) and sulfonic acid-based nanoporous carbon (CMK-5-SO3H) was assessed in relation to the green synthesis of 2-substituted benzimidazoles from aldehydes and benzene-1,2-diamine in open air in an aqueous medium. The results are rationalized in terms of the inclusion of the substrates inside hydrophobic cavities of the catalysts. Furthermore, the more hydrophobic and more water-resistant catalyst CMK-5-SO3H showed superior catalytic activity. Their excellent yields, their use of water as a green solvent, and their recyclability and environmentally friendly nature makes these catalysts important alternatives to classical acid catalysts.
- Zareyee, Daryoush,Rostamian Tuyehdarvary, Sakineh,Allahgholipour, Leila,Hossaini, Zinatossadat,Khalilzadeh, Mohammad A.
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p. 1251 - 1254
(2016/05/10)
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- CuI nanoparticles mediated expeditious synthesis of 2-substituted benzimidazoles using molecular oxygen as the oxidant
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A general and easy method for the synthesis of several 2-substituted benzimidazoles from cyclization of o-diaminobenzenes and various aldehydes using CuI nanoparticles as a heterogeneous catalyst is described. Short reaction times, easy and quick isolation of the products and excellent yields are the main advantages of this procedure. This CuI nanoparticles catalyst system was found to be air/O2 stable and also used for large scale cyclization reaction with recoverable and reusable properties without loss of catalytic activity for upto six cycles.
- Reddy, P. Linga,Arundhathi,Tripathi, Mohit,Rawat, Diwan S.
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p. 53596 - 53601
(2016/06/14)
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- Fe3O4@SiO2/collagen: An efficient magnetic nanocatalyst for the synthesis of benzimidazole and benzothiazole derivatives
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In this project, Fe3O4@SiO2 was synthesized and combined with collagen for the preparation of Fe3O4@SiO2/collagen. It was characterized by FT-IR, 1H NMR, VSM, XRD, EDX, SEM and T
- Ghafuri, Hossein,Esmaili, Elahe,Talebi, Majid
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p. 942 - 950
(2016/08/08)
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- Lewis acidic ionic liquids of crown ether complex cations: Preparation and applications in organic reactions
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A range of Lewis acidic ionic liquids composed of crown ether complex cations were designed, synthesised and characterised by Raman, MS, FT-IR, thermogravimetric differential thermal analysis (TGA-DSC) and elemental analysis. These Lewis acidic ionic liqu
- Liang, Yatao,Wang, Jinyuan,Cheng, Chen,Jing, Huangwang
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p. 93546 - 93550
(2016/10/21)
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- Rapid one pot synthesis of benzoimidazoles using MnO2 nanoparticles supported on silica as efficient oxidant agent under solvent-free conditions
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A novel one-pot and mild synthesis of benzoimidazole derivatives through the reaction of o-Phenylenediamine with aromatic aldehydes in the presence of MnO2 nanoparticles supported on silica as oxidizing agent under grinding conditions. The significant features of the present protocol are; simplicity of procedure, high products yields, purity of products, solvent-free condition, and easily work-up procedure.
- Naeimi, Hossein,Babaei, Zahra
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supporting information
p. 311 - 318
(2015/06/23)
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