67273-56-7Relevant academic research and scientific papers
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.
2-ARYLBENZIMIDAZOLES AS PPARGC1A ACTIVATORS FOR TREATING NEURODEGENERATIVE DISEASES
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Paragraph 85; 90, (2020/03/02)
A genus of compounds encompassed by formula (III) and their use is disclosed: Formula (III). The compounds activate Ppargc1a and, as a consequence, are useful for treating a variety of neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), Alzheimer's disease, Parkinson's disease, Huntington's disease, frontotemporal degeneration, dementia with Lewy bodies, motor neuron diseases, and a demyelinating disease.
Nickel catalysed construction of benzazoles: Via hydrogen atom transfer reactions
Adhikari, Debashis,Bains, Amreen K.,Dey, Dhananjay,Kundu, Abhishek,Yadav, Sudha
, p. 6495 - 6500 (2020/11/13)
Herein we report a homogeneous, phosphine free, inexpensive nickel catalyst that forms a wide variety of benzazoles from alcohol and diamines by a reaction sequence of alcohol oxidation, imine formation, ring cyclization and dehydrogenative aromatization. A reversible azo/hydrazo couple, that is part of the ligand architecture steers both the alcohol oxidation and dehydrogenation of the annulated amine under fairly mild reaction conditions. Interestingly, both the alcohol oxidation and amine dehydrogenation steps are directly mediated by hydrogen atom transfer (HAT), which is greatly facilitated by the reduced ligand backbone. The kH/kD for the amine dehydrogenation step, measured at 60 °C is 5.9, fully consistent with HAT as the rate determining factor during this step. This is a unique scenario where two consecutive oxidation steps towards benzazole formation undergo HAT, which has been substantiated via kinetic studies, KIE determination and intermediate isolation. This journal is
Transforming Oxadiazolines through Nitrene Intermediates by Energy Transfer Catalysis: Access to Sulfoximines and Benzimidazoles
Park, Do Dam,Min, Kwan Hong,Kang, Jihee,Hwang, Ho Seong,Soni, Vineet Kumar,Cho, Cheon-Gyu,Cho, Eun Jin
, p. 1130 - 1134 (2020/02/15)
Subtle differences in reaction conditions facilitated unprecedented photocatalytic reactions of oxadiazolines by energy transfer catalysis. A set of compounds, sulfoximines and benzimidazoles, were ingeniously prepared from oxadiazolines via nitrene intermediates by photocatalytic N-O/C-N bond cleavages. The synthesis of sulfoximines was realized through intermolecular N-S bond formation between nitrene intermediates and sulfoxides, whereas benzimidazoles were obtained via intramolecular aromatic substitution of the nitrene to the tethered aryl substituent.
Nanoporous Cu doped ZnS nanoparticles an efficient photo catalyst for the chemoselective synthesis of 2-substituted azoles via C-N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence in visible light
Dandia, Anshu,Bansal, Sarika,Sharma, Ruchi,Kumar Mahawar, Dinesh,Rathore, Kuldeep S.,Lal Meena, Mohan,Parewa, Vijay
, (2019/12/09)
ZnS and Cu:ZnS nanoparticles were prepared by aqueous chemical method and characterized by several analytical tools. Nanoparticles have an average size of about ～ 18 nm and possess highly open mesopores, moderate surface area, and uniform morphology. UV–vis spectra designate that doping of Cu shifted the optical response of the ZnS nanoparticles in to a visible region. These Cu:ZnS nanoparticles were employed as a photocatalyst for chemoselective synthesis of 2-substituted azoles by the reaction of benzyl bromides and 1,2-Diaminobenzene or 2-Mercaptoaniline in visible light. Analogous experiments confirmed that the reaction were proceeds through one pot C–N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence. The enhanced catalytic activity by doping could be attributed to the presence of trapping level generated by copper doping which augments the relaxation time of electron and holes so that they are easily available for the reaction. The method was also applicable for the synthesis of quinazolin-4(3H)-ones.
Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions
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Paragraph 0018; 0022, (2019/01/21)
The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.
Bimetallic Cu-Mn B spinel oxide catalyzed oxidative synthesis of 1,2-disubstituted benzimidazoles from benzyl bromides
Sharma, Rohit,Sofi, Firdoos Ahmad,Rana, Preeti,Bharatam, Prasad V.
supporting information, p. 4013 - 4016 (2019/03/08)
Cu-Mn B (a heterogeneous catalyst) catalyzed synthesis of 1-benzyl-2-phenyl-1H-benzo[d]imidazoles is reported. In this reaction, 2-phenyl-1H-benzo[d]imidazoles are found to be the side products. The reported protocol is simple and highly efficient, tolerates a wide variety of substrates and the products were formed in good to excellent yield.
Method for catalytically synthesizing benzimidazole compound by organic protonic acid under condition of no solvent
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Paragraph 0015; 0029, (2018/11/27)
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
Method for catalytically synthesizing benzimidazole compound in water phase under microwave radiation
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Paragraph 0033; 0049, (2017/07/19)
The invention discloses a method for catalytically synthesizing a benzimidazole compound in a water phase under microwave radiation. The method comprises the following steps: adding a catalytic amount of metal chloride, proline lithium and a substituted 2-halogenated aniline substrate, ammonia water, a benzaldehyde derivative, inorganic alkali and water into a reaction container; putting the reaction container into a microwave reaction instrument to react at certain temperature and under certain power; after certain time, decompressing and concentrating; purifying a product through a column chromatography to obtain the benzimidazole compound, wherein the metal chloride in the step is iron chloride, cobalt chloride, nickel chloride or copper chloride, the inorganic alkali in the step is sodium hydroxide, cesium carbonate, sodium carbonate, potassium hydroxide or potassium phosphate, and reaction temperature of the microwave reaction instrument is 20 DEG C to 200 DEG C. The method for preparing the benzimidazole compound, provided by the invention, is environmental-friendly, is simple and convenient to operate, is safe and cheap and is efficient. Compared with the prior art, the method has the advantages of moderate reaction conditions, simplicity in operation, high yield, safety, low cost and environmental friendliness.
Iron-catalyzed highly efficient aerobic oxidative synthesis of benzimidazoles direct from oximes in water
Yu, Jiatao,Lu, Ming
, p. 471 - 479 (2016/04/26)
This article presents a general and efficient method for aerobic oxidative synthesis of benzimidazoles from oximes catalyzed by Fe(NO3)3·9H2O under air in water. This practical method uses air as an economic and green oxidant, water as a green solvent, and tolerates a wide range of substrates that can afford the target benzimidazoles in moderate to good yields.
