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

Upstream product

• 325803-72-3 4-methyl-N-(4-methyl-2-nitrophenyl)benzamide 
• 104-87-0 4-methyl-benzaldehyde 
• 23244-46-4 3-phenyl-4-[1-p-tolyl-meth-(Z)-ylidene]-4H-isoxazol-5-one 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 25755-82-2 3-(4-methylphenyl)isoxazol-5(4H)-one 
• 89-62-3 4-methyl-2-nitroaniline 
• 874-60-2 4-methyl-benzoyl chloride 
• 1224442-21-0 4-methyl-N-(5-methyl-2-nitrophenyl)benzene carboximidamide 
• 16979-20-7 N-(4-methylbenzylidene)-4-methylaniline 
• 57387-51-6 N-3-methylphenyl-4-methylbenzaldimine 
• 106-49-0 p-toluidine 
• 108-44-1 1-amino-3-methylbenzene 
• 589-18-4 4-Methylbenzyl alcohol 
• 83392-35-2 methyl 3-(4-methylphenyl)-3-oxopropanedithioate 

Relevant academic research and scientific papers

Synthesis and evaluation of 2-aryl-1H-benzo[d]imidazole derivatives as potential microtubule targeting agents

Microtubule targeting agents (MTAs) are the potential drug candidates for anticancer drug discovery. Disrupting the microtubule formation or inhibiting the de-polymerization process by a synthetic molecule can lead to an excellent anticancer drug candidat

Transition-Metal-Free Transfer Hydrogenative Cascade Reaction of Nitroarenes with Amines/Alcohols: Redox-Economical Access to Benzimidazoles

This report describes an efficient transition-metal-free process toward the transfer hydrogenative cascade reaction between nitroarenes and amines or alcohols. The developed redox-economical approach was realized using a combination of KOtBu and Et3SiH as reagents, which allows the synthesis of benzimidazole derivatives via σ-bond metathesis. The reaction conditions hold well over a wide range of substrates embedded with diverse functional groups to deliver the desired products in good to excellent yields. The mechanistic proposal has been depicted on the basis of a series of control experiments, mass spectroscopic evidence which is well supported by density functional theory (DFT) calculations with a feasible energy profile.

Copper-Mediated Diamination of Arylboronic Acids for the Synthesis of 2-Aryl Benzimidazoles Using Trimethylsilyl Azide as the Amino Sources with Aldehydes

A direct and versatile copper-mediated three-component reaction of arylboronic acids, trimethylsilyl azide and aldehydes for the synthesis of benzimidazoles is reported. The reaction is well tolerated by a wide range of substituted aromatic aldehydes and aromatic boronic acids to produce the corresponding benzimidazoles in moderate to high yields. Mechanism investigations demonstrated that copper-promoted Chan-Evans-Lam coupling, C?H amination, and oxidative cycloaddition are involved in the tandem processes. (Figure presented.).

Bimetallic Cu-Mn B spinel oxide catalyzed oxidative synthesis of 1,2-disubstituted benzimidazoles from benzyl bromides

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.

Aerobic {Mo72V30} nanocluster-catalysed heterogeneous one-pot tandem synthesis of benzimidazoles

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.

Sulfonic-acid-functionalized activated carbon made from tea leaves as green catalyst for synthesis of 2-substituted benzimidazole and benzothiazole

Abstract: A simple and efficient procedure for synthesis of 2-substituted benzimidazole and benzothiazole has been developed by using sulfonic-acid-functionalized activated carbon as heterogeneous catalyst. The activated material was prepared from matured tea leaf in presence of phosphoric acid as activating agent. The final catalyst was prepared by anchoring –SO3H group on the surface of the activated carbon. The catalyst could be easily recovered and reused for more than three catalytic cycles without significant loss in catalytic activity. The catalytic performance of the catalyst was found to be superior to that of a similar catalyst prepared from montmorillonite K10. Graphical Abstract: [Figure not available: see fulltext.].

A Tandem Aerobic Photocatalytic Synthesis of Benzimidazoles by Cobalt Ascorbic Acid Complex Coated on TiO2 Nanoparticles Under Visible Light

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.].

Selective Synthesis of 2-Substituted and 1,2-Disubstituted Benzimidazoles Directly from Aromatic Diamines and Alcohols Catalyzed by Molecularly Defined Nonphosphine Manganese(I) Complex

Herein, we present a selective synthesis of 2-substituted and 1,2-disubstituted benzimidazoles by acceptorless dehydrogenative coupling of aromatic diamine with primary alcohols. The reaction is catalyzed by a phosphine-free tridentate NNS ligand-derived manganese(I) complex.

Eco-friendly highly efficient solvent free synthesis of benzimidazole derivatives over sulfonic acid functionalized graphene oxide in ambient condition

Abstract: Sulfonated graphene oxide (GO-HSO3) heterogeneous catalyst was prepared at molecular level and characterized by using various modern analytic and spectroscopic methods. Using prepared heterogeneous catalyst GO-HSO3, benzimidazole synthesis was carried out by means of reacting diamine and aldehyde at room temperature in solvent free condition. The catalyst GO-HSO3 showed tremendous catalytic activity in selective synthesis of benzimidazole, as a result 100?% conversion of reactants and up to 89.0?% yield of respective benzimidazole was achieved using 0.1?mg of catalyst in very short reaction duration. The GO-HSO3 catalyst was separated from the reaction mixture by simple filtration process at the end of reaction and reused for six successive cycles without noteworthy loss of catalytic activity and selectivity. Key advantageous of this protocol is high yield, low cost, and easy work-up procedure as well as short reaction time and solvent free condition. The present method is found eco-friendly, highly efficient, solvent free, high yielding, and clean method for the synthesis benzimidazole derivatives at room temperature. Graphical Abstract: [Figure not available: see fulltext.]

Br?nsted acid-catalyzed metal-free one-pot synthesis of benzimidazoles via [4+1] heteroannulation of ortho-phenylenediamines with β-oxodithioesters

An operationally simple and user-friendly one-pot domino protocol for the synthesis of 2-aryl/hetaryl benzimidazoles has been devised from easily available and inexpensive 1,2-phenylenediamines and β-oxodithioesters. The strategic [4+1] heteroannulation i