23982-82-3

Upstream product

• 80165-57-7 2-(4-methylbenzylidene)-1-benzyl-1-phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 62-53-3 aniline 
• 2829-25-6 4-methylbenzaldehyde phenylhydrazone 
• 5729-06-6 N-benzyl-2-nitroaniline 
• 104-87-0 4-methyl-benzaldehyde 
• 100-39-0 benzyl bromide 
• 5822-13-9 N-benzyl-1,2-phenylenediamine 
• 1493-27-2 ortho-nitrofluorobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 100-46-9 benzylamine 
• 4981-92-4 1-benzylbenzimidazole 
• 106-43-4 para-chlorotoluene 
• 76464-99-8 N-benzyl-2-iodoaniline 

Relevant academic research and scientific papers

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.

Design, synthesis, characterization, and in vitro cytotoxic activity evaluation of 1,2-disubstituted benzimidazole compounds

A series of 2-p-tolyl-1H-benzo[d]imidazole derivatives were synthesized and characterized. For finding an effective anticancer drug, which could be used in future generations, the developed heterocyclic compounds were screened in the human epithelial breast adenocarcinoma cell line (MCF-7) and human liver epithelial hepatocellular carcinoma cell line (HepG2) using the MTT assay method. Two positive control drugs were used for comparison with the compounds. The substituents on the 1- and 2-positions of the benzimidazole core had an important effect on the antiproliferation of cancerous cells. According to the results obtained, a compound, namely, 1-(4-methylbenzyl)-2-p-tolyl-1H-benzo[d]imidazole, which has electron donating groups (CH3) in the para position of a phenyl ring, showed higher cytotoxic activities compared to other compounds towards liver and breast cell lines. The compounds were found to have more cytotoxicity in HepG2 rather than MCF-7.

Intramolecular C(sp3)–H Imination towards Benzimidazoles Using Tetrabutylammonium Iodide and tBuOOH

Development of sustainable and economically viable methods is challenging but desired in organic synthesis. Herein, intramolecular C(sp3)–H imination between a free amine group and N-methylene group is established using TBAI (20 mol %)-TBHP (3.0 equiv.) in DMSO which is found to be an inexpensive replacement of PhI-mCPBA in HFIP.

Synthesis of 1,2-disubstituted benzimidazoles through DDQ-oxidized intramolecular dehydrogenative coupling of N,N′-dialkyl o-phenylenediamines

The synthetic methodology of 1,2-disubstituted benzimidazoles has been developed, which starts from N,N′-dialkyl o-phenylenediamines via intramolecular dehydrogenative coupling under the oxidation of DDQ with mild conditions. Through detailed optimization of reaction conditions, only DDQ was found essential without any additives to reach to the highest yield of 99%. In the cases of linear aliphatic substituents, the synthesis of 1-alkyl-2-phenylbenzimidazoles showed high selectivities and their structures were identified by 2D NMR COSY correlation analysis. A plausible mechanism was proposed to interpret the observed reactivities and selectivities.

Benzimidazole compound with endothelial lipase inhibition effect and application of benzimidazole compound

The invention discloses a benzimidazole compound with an endothelial lipase inhibition effect and application of the benzimidazole compound, and belongs to the technical field of medicines. The benzimidazole compound has an excellent inhibition effect on endothelial lipase, can effectively treating atherosclerosis and sequelae thereof, such as coronary heart disease, and also promotes treatment onmetabolic syndrome and sequelae thereof, such as diabetes. The benzimidazole compound provided by the invention has good solubility in an aqueous medium, also has good biological activity and metabolic stability, and shows advantages in the aspect of serum stability.

An intramolecular C(sp3)-H imination using PhI-m CPBA

Herein, a highly exothermic primary amine-polyvalent iodine reaction has been used successfully for selective functionalization of acidic C(sp3)-H groups for a dehydrogenative C-H imination reaction by 4H elimination. Overall, C(sp3)-H imination at 1,5 distances was readily done via organocatalysis using PhI (10 mol%)-mCPBA under ambient conditions.

One-pot strategy of copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles

A simple, one-pot and copper-catalyzed coupling reaction for the construction of 1,2-disubstituted benzimidazole derivatives is described. A low-cost copper salt and a weak base K3PO4 were utilized in this reaction. A variety of 1,2-disubstituted benzimidazoles were obtained in moderate to excellent yields.

N -heterocyclic carbene-palladium(II)-1-methylimidazole complex-catalyzed direct C-H bond arylation of (Benz)imidazoles with aryl chlorides

(Benz)imidazoles can be efficiently functionalized by (hetero)aryl chlorides via direct C-H bond arylation in the presence of a well-defined NHC-Pd(II)-Im complex. Under the optimal conditions, various activated, unactivated, and deactivated (hetero)aryl chlorides were successfully applied as the arylating reagents to achieve the 2-(hetero)aryl (benz)imidazoles in acceptable to high yields, giving a facile and alternative methodology for the direct C-H bond arylation of (benz)imidazoles.

"All-water" one-pot diverse synthesis of 1,2-disubstituted benzimidazoles: Hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' by water

A new "all-water" tandem arylaminoarylation/arylaminoalkylation- reduction-cyclisation route is reported for one-pot diversity oriented synthesis of regiodefined 1,2-disubstituted benzimidazoles. Water plays a crucial and indispensable role through hydrogen bond driven 'synergistic electrophile-nucleophile dual activation' in the formation of N-mono-aryl/aryl alkyl/alkyl/cycloalkyl o-nitroanilines under metal and base-free conditions to replace the transition metal-based C-N bond formation (aryl amination) chemistry and underlines the origin of regiodefined installation of the diverse selection of aryl, aryl alkyl, and alkyl/cycloalkyl groups as substituents on the benzimidazole scaffold to form the 1,2-disubstituted benzimidazoles. The influence of the hydrogen bond effect of water in promoting the arylaminoarylation reaction under base and metal-free conditions has been realized through observation of inferior yields in D2O compared to that obtained in water during the reaction of o-fluoronitrobenzene with aniline separately performed in water and D2O under similar experimental conditions. Water also provides assistance in promoting the subsequent nitro reduction and in the final cyclocondensation steps. The role of water in promoting the cyclocondensation reaction through hydrogen bonds is realized by the differential product yields during the reaction of mono-N-phenyl-o- phenylenediamine with benzaldehyde performed separately in water and D 2O. The better hydrogen bond donor and hydrogen bond acceptor abilities of water compared to those of the organic solvents are the contributing/deciding factors for making the new water-assisted tandem arylaminoarylation/arylaminoalkylation-reduction-cyclisation strategy for the diversified synthesis of the regiodefined 1,2-disubstituted benzimidazoles effective in an aqueous medium, making it represent a true "all-water chemistry."

"All-water" chemistry of tandem N-alkylation-reduction- condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles

A water-assisted tandem N-alkylation-reduction-condensation process has been devised as a new synthetic route for the one-pot synthesis of N-arylmethyl-2-substituted benzimidazoles. Water plays the crucial and indispensable role through hydrogen bond mediated 'electrophile-nucleophile dual activation' in promoting selective N-monobenzylation of o-nitroanilines as an alternative to the transition metal-based chemistry for C-N bond formation (amination) and forms the basis of disposing the substituents on the benzimidazole moiety in regiodefined manner. Water also exerts a beneficial effect in the condensation of N-monobenzylated o-phenylenediamines with aldehydes. The water-assisted C-N bond formation chemistry led to metal/base-free synthesis of N-monobenzylated o-nitroanilines and N-monobenzylated o-phenylenediamines. The indispensable/advantageous role of water in the various stage of the N-alkylation-reduction-condensation process exemplifies an 'all-water' chemistry for the synthesis of N-arylmethyl-2- substituted benzimidazoles.