58758-09-1

Upstream product

• 615-15-6 2-Methyl-1H-benzimidazole 
• 14371-10-9 (E)-3-phenylpropenal 
• 95-54-5 1,2-diamino-benzene 
• 100-52-7 benzaldehyde 
• 140-10-3 (E)-3-phenylacrylic acid 
• 615-28-1 o-phenylenediamine dihydrochloride 
• 104-55-2 3-phenyl-propenal 
• 74710-09-1 o-phenylenediamine sulphate 
• 89812-50-0 (E)-1,1-bis(methylthio)-5-phenylpenta-1,4-dien-3-one 
• 28144-70-9 anthranilic acid amide 
• 175531-13-2 2-bromomethyl-1-tert-butoxycarbonylbenzimidazole 
• 4392-24-9 Cinnamyl bromide 
• 130964-01-1 N¹-cinnamylbenzene-1,2-diamine 
• 59066-63-6 (E)-1-methyl-2-styryl-1H-benzo[d]imidazole 

Downstream Products

• 2849-93-6 2-benzimidazolecarboxylic acid 
• 59066-63-6 (E)-1-methyl-2-styryl-1H-benzo[d]imidazole 
• 1307837-03-1 (E)-1,3-diallyl-2-styryl-3H-benzo[d]imidazol-1-ium bromide 
• 1849-01-0 1-methyl-2-benzimidazolone 
• 56547-44-5 N-vinyl-2-styrylbenzimidazole 

Relevant academic research and scientific papers

Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon

A one-pot direct synthesis of a wide range of biologically active benzimidazoles through coupling of phenylenediamines and aldehydes catalyzed by a highly recyclable nonnoble cobalt nanocomposite was developed. A broad set of benzimidazoles can be efficiently synthesized in high yields and with good functional-group tolerance under additive- and oxidant-free mild conditions. The catalyst can be easily recycled for successive uses, and the process permits gram-scale syntheses of benzimidazoles.

Sulfonated carbon-encapsulated iron nanoparticles as an efficient magnetic nanocatalyst for highly selective synthesis of benzimidazoles

Surface functionalized carbon-encapsulated iron nanoparticles (CEINs) were found to be a magnetic nanocatalyst for the efficient and highly selective synthesis of benzimidazoles. CEINs were covalently decorated with carboxyl or sulfonyl groups and their catalytic activity was examined. Carboxyl-modified CEINs were obtained via the radical or oxidative treatment, whilst the sulfonated CEINs were obtained using the one-step diazotization approach with sulfanilic acid and isoamyl nitrite. The content of surface acidic groups varied between the obtained materials and was found to be the highest for sulfonyl-modified CEINs. CEINs functionalized with sulfonyl groups were the most efficient and the most selective nanocatalyst for the synthesis of benzimidazoles. Various benzimidazoles were obtained in very high yields (92.5-97.0%). Both metallocene, aliphatic, heterocyclic and aromatic aldehydes substituted with different functional groups were subjected to the synthesis process. The reaction proceeded in a short time, which varied from 25 min to 65 min depending on the aldehyde used. Additionally, the mechanism of the studied catalytic condensation by applying sulfonated CEINs as the catalyst was discussed. Importantly, the developed magnetic nanocatalysts could be easily separated from the reaction mixture using a permanent magnet. The nanocatalysts can be used up to six reaction cycles without any significant loss of their catalytic activity. This work opens up new ways for very efficient and simple synthesis of benzimidazoles-an important class of organic compounds for various biomedical applications.

Benzimidazole compounds having activity against hepatitis B viruses and antibacterial activity, and a synthetic method and application thereof

Benzimidazole compounds having activity against hepatitis B viruses and antibacterial activity, and a synthetic method and application thereof are disclosed. Structures of the compounds are shown as ageneral formula (I) in the description. The synthetic method of the compounds, and the application of the compounds in preparation of medicines against hepatitis B viruses are also disclosed. The compounds have certain anti-HBV activity and antibacterial activity, and the activity against hepatitis B viruses of the compounds is equivalent to that of tenofovir that is a clinical anti-HBV medicine.Antibacterial activity screening shows that the compounds have good suppressing activity for Staphylococcus aureus. In the fields of compound structures, synthetic methods and bioactivity, the compounds have significant scientific significance and application prospects for developing novel anti(hepatitis B) medicines of a novel structure type and antibacterial medicines.

Concentrated solar radiation promoted unconventional greener approach: Solvent-free benign synthesis of functionalized benzimidazoles

Renewable concentrated solar-radiation (CSR) offered a promising en route for the development of practical, highly efficient, scalable, catalyst free and solvent-free clean process leading to the synthesis of functionalized benzimidazoles. Developed protocol has a very good substrate scope, involves mild reaction conditions and products obtained in good to excellent yields. Method presented the observations in which light alone could affect the remarkable changes with more than 85% energy saving and 75% less reaction time in listed organic transformations.

I2/TBHP promoted oxidative C–N bond formation at room temperature: Divergent access of 2-substituted benzimidazoles involving ring distortion

A new ‘one pot’ tandem synthesis of 2-substituted benzimidazoles has been developed from 2-aminobenzyl alcohol/2-aminobenzamide and different coupling partners (nitriles, aldehydes and 1,3-diketones) via iodine and TBHP promoted oxidative ring contraction. The present strategy involves sequential C–N bond formation, cyclization, subsequent ring contraction and dehydrogenation to afford various medicinally important benzimidazole derivatives in moderate to good yields. This operationally simple synthetic approach proceeds at room temperature under base-free condition, broadly applicable to a wide array of nitriles and aldehydes bearing oxidation prone functional groups and noteworthy to mention that various acyclic 1,3-diketones undergo selective C–C bond cleavage leading to 2-alkyl benzimidazoles under mild condition.

Diphosphorus tetraiodide (P2I4): An efficient catalyst for synthesis of 2-Aryl-1,3-benzazoles via cyclocondensation of o-Amino/Mercaptan/Hydroxy anilines with aryl acids

An efficient and versatile approach for the synthesis of 2-substituted 1,3-benzazoles has been developed via diphosphorus tetraiodide (P2I4) catalyzed condensation reaction of ortho-substituted anilines (–NH2, –SH and –OH) with various aromatic acids to give benzimidazoles, benzothiazoles and benzoxazoles in excellent yields. Additionally, the synthetic approach reported herein has advantages such as mild reaction conditions, broad substrate scopes as well as simple one-pot operation, common for all the three 1,3-benzazoles, which makes this strategy highly attractive.

Enantioselective aza Michael-type addition to alkenyl benzimidazoles catalyzed by a chiral phosphoric acid

Highly enantioselective Michael-type addition (MTA) reactions between N-protected alkenyl benzimidazoles and either pyrazoles or indazoles as nitrogen nucleophiles are accomplished for the first time using chiral phosphoric acid catalyst. Theoretical studies elucidated the reaction pathway and the origin of the stereochemical outcomes, where the catalyst substituent and the N-protecting group of benzimidazole contributed to the resulting high enantioselectivity. Heterocycle squared: Highly enantioselective Michael-type addition reactions to alkenyl benzimidazoles with pyrazoles and indazoles as nitrogen nucleophiles are accomplished using a chiral phosphoric acid catalyst. Theoretical studies elucidated the reaction pathway and the origin of the stereochemical outcome. The catalyst substituent and the N-protecting group (PG) of the benzimidazole contribute to the resulting high enantioselectivity.

POCl3-mediated synthesis of 2-substituted benzimidazolyl-coumarin, benzimidazolyl-indole, and styrylbenzimidazole derivatives

2-Substituted benzimidazolyl heterocycles and styrylbenzimidazoles have been synthesized by the reaction of substituted o-phenylenediamine with different heterocyclic carboxylic acids and cinnamic acid respectively in the presence of POCl3as a

An efficient one-pot two catalyst system in the construction of 2-substituted benzimidazoles: Synthesis of benzimidazo[1,2-c]quinazolines

The benzimidazole core is a common moiety in a large number of natural products and pharmacologically active small molecules. The synthesis of novel benzimidazole derivatives remains a main focus in medicinal research. In continuation of the efforts towards Ce(iii) catalysts for organic transformations, we observed for the first time the activity of the iodide ion and copper cation in activating CeCl3·7H2O in the selective formation of prototypical 2-substituted benzimidazoles. The one-pot CeCl3·7H2O-CuI catalytic system procedure includes the cyclo-dehydrogenation of aniline Schiff's bases, generated in situ from the condensation of 1,2-phenylenediamine and aldehydes, followed by the oxidation with iodine, which works as a hydrogen sponge. Mild reaction conditions, good to excellent yields, and clean reactions make the procedure a useful contribution to the synthesis of biologically active fused heterocycles containing benzimidazoquinazolines.

Significant facilitation of metal-free aerobic oxidative cyclization of imines with water in synthesis of benzimidazoles

A simple, convenient, and environmentally benign protocol for the synthesis of benzimidazoles from ortho-phenylenediamines and aldehydes via aerobic oxidation was developed in wet organic solvents. Notably, water significantly accelerated this transformation, which allowed us to achieve this important transformation without the assistance of any metal catalysts and other co-oxidants. Mechanistic studies suggested that water acts as the nucleophilic catalyst for this transformation by the conversion of disfavored 5-endo-trig cyclization of imines to favored 5-exo-tet cyclization via tetrahedral intermediates and the subsequent aerobic oxidation of the resulting benzimidazolines affords benzimidazoles.