2620-78-2

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InChI:InChI=1/C15H14N2/c1-11-7-9-12(10-8-11)15-16-13-5-3-4-6-14(13)17(15)2/h3-10H,1-2H3

Upstream product

• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 1632-83-3 1-Methylbenzimidazole 
• 5720-05-8 4-methylphenylboronic acid 
• 6832-87-7 2-bromo-N-methylaniline 
• 619-55-6 para-methylbenzamide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 104-87-0 4-methyl-benzaldehyde 
• 80252-45-5 N-methyl-N-phenyl-4-methylphenylamidine 
• 106-49-0 p-toluidine 
• 36719-51-4 3,3-diethyl-1-(4-methylphenyl)-1-triazene 
• 104-93-8 p-methylanizole 
• 41468-10-4 α-hydroxy-α-toluenesulfonate 
• 1849-02-1 2-chloro-1-methyl-benzimidazole 
• 4294-57-9 para-methylphenylmagnesium bromide 

Downstream Products

• 68874-21-5 1,3-dimethyl-2-(4-methylphenyl)-1H-benzimidazolium iodide 

Relevant academic research and scientific papers

Electrochemical Synthesis of Benzimidazoles via Dehydrogenative Cyclization of Amidines

The development of efficient and sustainable methodologies for the synthesis of N-heterocycles is a constant focus of organic synthesis. Herein an electrochemical method is reported for the synthesis of benzimidazoles through dehydrogenative cyclization of easily available N-aryl amidines. The reactions were conducted under simple constant current conditions in an undivided cell without need for catalysts, chemical oxidants, or additives, and produced H2 as the only theoretical byproduct.

Pyrazole-3-carboxylates assisted N-heterocyclic carbene palladium complexes: synthesis, characterization, and catalytic activities towards arylation of azoles with arylsulfonyl hydrazides

Four mononuclear and dinuclear pyrazole-3-carboxylates assisted NHC–Pd complexes have been synthesized and characterized. Notably, the bridge-cleavage reactions of [Pd(μ-Cl)(Cl)(NHC)]2 with 1H-pyrazole-3-carboxylic acid afforded dinuclear complexes [(NHC)Pd(μ-1H-pyrazolato-3-carboxylate)]2, in which the 1H-pyrazolato-3-carboxylate was employed as a N^N^O dianionic chelating and bridging ligand. To further explore the structural features and catalytic properties of the complexes, 1-methyl-1H-pyrazole-3-carboxylic acid was introduced into the coordination with [Pd(μ-Cl)(Cl)(NHC)]2 and the corresponding mononuclear complexes (NHC)PdCl(1-methyl-1H-pyrazole-3-carboxylate) were obtained. The catalytic properties of the complexes in desulfitative arylation of azoles with arylsulfonyl hydrazides were initially investigated.

Photoinduced Heterogeneous C?H Arylation by a Reusable Hybrid Copper Catalyst

Heterogeneous copper catalysis enabled photoinduced C?H arylations under exceedingly mild conditions at room temperature. The versatile hybrid copper catalyst provided step-economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS analysis of the hybrid copper catalyst, among others, supported its outstanding stability and reusability.

Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes

A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

Nickel-Catalyzed Heteroarenes Cross Coupling via Tandem C-H/C-O Activation

Inert aryl methyl ethers as coupling components via C-O activation have been established with a Ni catalyst for C-H activation of heteroarene. The key to simultaneous C-H/C-O bond activation is the use of sterically demanding o-tolylMgBr. The protocol is effective for a wide scope of substrates including naphthyl methyl ethers, anisoles, and a variety of other heteroarene derivatives. Detailed mechanistic studies indicated that the C-O cleavage is assisted via synergistic effect of nickel and Grignard reagent in this C-H/C-O reaction, which is supported by DFT calculation. At this stage, single-electron transfer can be ruled out as a main operative process for this tandem strategy.

Ring-expanded N-heterocyclic carbenes as ligands in iron-catalysed cross-coupling reactions of arylmagnesium reagents and aryl chlorides

The structure-activity relationship of expanded-ring N-heterocyclic carbenes (NHCs) in the iron-catalysed Kumada aryl-aryl coupling reaction was explored. This was achieved by comparing the catalytic performance of Fe-NHC catalysts generated in situ containing NHCs that differ in steric bulk. In particular, the influences of ring sizes (5-8) and N-aryl substituents were explored in terms of spectroscopic and structural features, which affect their %Vbur values. The three best performing ligands were found on a diagonal of a 5 × 4 structural matrix revealing an optimal steric bulk and significant influences of subtle steric variations on the catalytic activities.

Microwave assisted synthesis and potent antimicrobial activity of some novel 1,3-dialkyl-2-arylbenzimidazolium salts

Background: Benzimidazolium salts include biologically active benzimidazole ring. Some benzimidazolium salts and their metal complexes, containing different groups, showed remarkable antibacterial, antifungal and antitumor effects. Most of these studies are generally related with the 2-unsubstituted derivatives of benzimidazolium salts which named as N-heterocyclic carbenes (NHCs). To enhance the efficacy of the benzimidazoles in the biological systems, it is very important to overcome the insolubility problem. For this reason and previously indicated structural importance of the benzimidazolium salts, 1,3-dialkyl halide salts of the 2-arylbenzimidazoles, are of focus in this work. To the best of our knowledge, this is the first report that describes the microwave assisted synthesis and antimicrobial activity of 2-arylsubstituted benzimidazolium salts. Methods: A series of novel 1,3-dialkyl-2-arylbenzimidazolium salts (8-28) were synthesized via the N-alkylation of 1-methyl-2-arylbenzimidazole derivatives (1-7) with alkyl halides under microwave conditions by using small amount of DMF. The results were also compared with conventional heating under reflux. Structures of the products were confirmed by using 1H-NMR, 13C-NMR, FTIR spectroscopic techniques. All of the synthesized compounds were screened for their in vitro antimicrobial activities using microbroth tube dilution and disc diffusion methods. Results: Considering the reactions repeated by classical heating, it was determined that the reaction times were decreased from 3-6 hours to 5-35 minutes under microwave. Additionally, yields have increased from 4-71 % to 64-96 % ranges. Considering the whole antimicrobial activity studies, MIC values of newly synthesized benzimidazolium salts 8-28 (1.95->1500 μg/ml) are remarkably smaller than parent benzimidazoles 1-7 (62.5->1500 μg/ml) on the studied microorganisms. Conclusion: The microwave method is advantageous regarding the usage of mild conditions and small amounts of solvent, easy purification and achieving high yields in short times. The antimicrobial activity studies demonstrate that newly synthesized salts (8-28) are effective mostly on grampositives and eukaryotic microorganisms. Compounds 16, 18, 19, 24, 25 and 27 were found to be the most effective inhibitors of growth in both gram-positive bacteria and eukaryotes. Thus, the synthesized compounds in this study may aid the treatment of fungal and bacterial diseases. The results of this study are of great significance in the areas of synthetic organic chemistry, microbiology, pharmaceutical chemistry and chemical catalysis.

Catalytic Oxidative Coupling of Primary Amines under Air: A Flexible Route to Benzimidazole Derivatives

Benzimidazoles are of fundamental importance in chemistry and biology, and the development of efficient, environmentally benign methods for their preparation remains a key challenge for organic chemists. In a biomimetic approach inspired by copper amine oxidases, we disclose herein the scope and factors influencing the success of the cooperative action of CuBr2 as electron-transfer mediator and a topaquinone-like substrate-selective catalyst in the oxidative cyclocondensation of primary amines with o-aminoanilines. This one-pot atom-economic multistep process, which works under green conditions with ambient air as the terminal oxidant, low loadings of catalyst, and equimolar amounts of commercially available amine substrates, is particularly suitable for the preparation of 1,2-disubstituted benzimidazoles. Furthermore, it allows the functionalization of nonactivated primary aliphatic amines, which are known to be challenging substrates for non-enzymatic catalytic aerobic systems.

Synthesis of 2-substituted benzimidazoles and benzothiazoles using Ag2CO3/Celite as an efficient solid catalyst

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.

Nanoparticle mediated organic synthesis (NAMO-synthesis): CuI-NP catalyzed ligand free amidation of aryl halides

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