30384-79-3

Upstream product

• 771-97-1 2,3-Diaminonaphthalene 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 873-67-6 benzonitrile oxide 
• 109670-70-4 2-methyl-4-phenyl-3H-naphtho[2,3-b][1,4]diazepine 
• 7732-18-5 water 
• 86255-33-6 N-(3-aminonaphthyl)benzamide oxime 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 65-85-0 benzoic acid 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 31378-03-7 1-phenyl-2-tosylethanone 
• 100-39-0 benzyl bromide 
• 1608149-20-7 N²-benzylnaphthalene-2,3-diamine 

Relevant academic research and scientific papers

Anti-BVDV activity evaluation of naphthoimidazole derivatives compared with parental imidazoquinoline compounds

Background: Pestivirus genus includes animal pathogens which are involved in economic impact for the livestock industry. Among others, Bovine Viral Diarrhoea Virus (BVDV) establish a persistent infection in cattle causing a long list of symptoms and a high mortality rate. In the last decades, we synthesised and reported a certain number of anti-BVDV compounds. Methods: In them, imidazoquinoline derivatives turned out as the most active. Their mechanism of actions has been deeply investigated, BVDV RNA-dependent RNA polymerase (RpRd) resulted as target and the way of binding was predicted in silico through three main H-bond interaction with the target. The prediction could be confirmed by target or ligand mutation. The first approach has already been performed and published confirming the in silico prediction. Results: Here, we present how the ligand chemical modification affects the anti-BVDV activity. The designed compounds were synthesised and tested against BVDV as in silico assay negative control. Conclusion: The antiviral results confirmed the predicted mechanism of action, as the newly synthesised compounds resulted not active in the in vitro BVDV infection inhibition.

Reactions of 3-(Polyfluoroalkyl)propane-1,2,3-trione-2-oximes with Diaminoarenes

Novel quinoxaline derivatives have been synthesized via the reaction of 3-trifhioromethyl-1,2,3-propanetrione-2-oximes with 1,2-diaminobenzene or 2,3-diaminonaphthalene: 2-trifluoromethyl-3-aroylquinoxaline and 2-trifluoromethyl-3-aroylbenzo[g]quinoxaline. Under similar conditions, 3-RF-1,2,3-propanetrione-2-oximes [RF = C3F7, H(CF2)4, C4F9, and C6F13] with the same diaminoarenes have given a mixture of the condensation and fragmentation products in different ratios. The structure of (4-methylphenyl)[3-(tri-fluoromethyl)benzo[g]quinoxalin-2-yl]methanone has been elucidated by means of X-ray diffraction analysis.

Metal-free TEMPO-promoted C(sp3)-H amination to afford multisubstituted benzimidazoles

An efficient TEMPO-air/cat. TEMPO-O2 oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp3 C-H and free N-H of readily available N1-benzyl/alkyl-1,2-phenylenediamines.

Synthesis of 2-arylbenzimidazole analogues

Substituted 2-arylbenzimidazoles (4) were easily synthesized in good yields starting from the condensation reaction of 1,2-diaminobenzenes (1) with β-ketosulfones (5) in the presence of boiling HOAc.

Copper-catalyzed synthesis of benzazoles via aerobic oxidative condensation of o-amino/mercaptan/hydroxyanilines with benzylamines

A simple and efficient method for the synthesis of benzazoles via Cu-catalyzed aerobic oxidative condensation of o-amino/mercaptan/hydroxyanilines with benzylamines was developed.

A simple and efficient one step synthesis of benzoxazoles and benzimidazoles from carboxylic acids

Benzoxazoles or benzimidazoles can be rapidly and efficiently synthesized from a variety of carboxylic acids with 2-aminophenols or 1,2-phenylenediamines in one simple step, respectively. The use of commercially available PS-PPh3 resin combined with microwave heating delivered a variety of benzoxazoles and benzimidazoles in high yields and purities.

Microwave-assisted one step high-throughput synthesis of benzimidazoles

One-pot synthesis of benzimidazoles from diamines and carboxylic acids was developed under microwave irradiation condition, which provided a practical and efficient method for high-throughput synthesis of this important class of heterocyclic compounds.

A novel palladium-catalyzed synthesis of 2-arylbenzimidazoles

A new method for the preparation of 2-arylbenzimidazoles based on the palladium-catalyzed carbonylation, coupling, and cyclization of haloaromatics and o-phenylenediamines is described. Reactions were run in DMAc at 145°C for 18 h, under 95 psig CO, with 1.5 mol% PdCl2L2 as catalyst and in the presence of 1.2 equiv of 2,6-lutidine to give 70-98% yield of desired products. This route is tolerant of a variety of functional groups and nicely complements the classical route where the desired benzoic acid derivatives are unavailable. The selection of an appropriate base is crucial for the formation of 2-arylbenzimidazoles. Intermolecular bis-acylation to form bisamides occurs if the base is too strong. Weak bases allow side reactions with amide solvents to occur, leading to substituted benzamides and alkyl benzimidazoles.