10205-84-2

Upstream product

• 52764-31-5 α-(4-methoxyphenyl)-N-(p-tolyl)-nitrone 
• 111270-65-6 N-(2-bromo-4-methyl phenyl)-4-methoxybenzamide 
• 959055-30-2 N-(2-iodo-4-methylphenyl)-4-methoxybenzamide 
• 583-68-6 2-bromo-p-toluidine 
• 100-07-2 4-methoxy-benzoyl chloride 
• 2835-98-5 2-Hydroxy-4-methylanilin 
• 123-11-5 4-methoxy-benzaldehyde 
• 10531-80-3 6-methyl-1,3-benzoxazole 

Downstream Products

• 67563-36-4 6-bromomethyl-2-(4-methoxy-phenyl)-benzooxazole 

Relevant academic research and scientific papers

Synthesis of benzoxazoles by an efficient ullmann-type intramolecular CO bond-forming coupling cyclization with a BINAM-copper(II) catalyst

A wide range of 2-substituted benzoxazoles were synthesized from the corresponding N-(2-iodophenyl)benzamides through intramolecular CO bond formation via Ullmann-type coupling cyclization in the presence of a catalytic amount of an easily available BINAM-copper(II) complex under very mild reaction conditions (82C). Less reactive bromo and chloro analogues of the N-(2-halophenyl)benzamides were also successfully cyclized to produce benzoxazoles, without increasing the catalyst loading. Georg Thieme Verlag Stuttgart · New York.

Synthesis method of Tafamidis and derivative thereof

The invention provides a synthesis method for preparing Tafamidis and a derivative thereof from 6-amino-m-cresol and an aldehyde compound under the action of sodium periodate and potassium permanganate. In the method, the use of an acylation reagent dichlorobenzoyl chloride and an esterification reagent (trimethylsilyl) diazomethane is avoided, and the problem that acyl chloride, a diazonium reagent, a strong acid and strong alkali additive and the like are harmful to the environment is solved; the reaction steps are few, and the total yield is high; methoxy, halogen, trifluoromethyl and the like can be well tolerated; and the iodate and the manganese dioxide after the reaction are insoluble in the reaction solution and can be well recycled, so that the pollution caused by the reaction system is greatly reduced, a more economical and environment-friendly path is provided for synthesis of Tafamidis and the derivative thereof, and the method has a huge application value.

Novel and efficient heterogeneous polymer supported copper catalyst for synthesis of 2-substituted Benzoxazoles from 2-Haloanilides

A novel polymer supported copper complex is prepared by the immobilization of copper iodide on chemically modified polyacrylonitrile and its application in heterogeneous catalysis is described. The catalyst was prepared by easy method via synthetic modification of Polyacrylonitrile (PAN) using ethylene diamine followed by the complexation with CuI. After characterization, this complex was explored as a green and efficient heterogeneous catalyst for the synthesis of 2-benzoxazoles from 2-haloanilides. The reaction was performed without adding additional ligand and the catalyst shows activity over a broad range of substrates with quantitative product yields. The catalyst was easily recovered by simple filtration and reused successfully for further cycle.

Zr and Hf-metal-organic frameworks: Efficient and recyclable heterogeneous catalysts for the synthesis of 2-arylbenzoxazole via ring open pathway acylation reaction

Zirconium- and hafnium-based metal–organic frameworks which constructed by 12-coordinated clusters and 6-coodinated clusters were shown to be highly effective heterogeneous catalysts for the ring opening acylation of benzoxazole to 2-arylbenzoxazole under solvent free conditions. Owning the wide opening spaces structures and inherent formate sites, MOFs based on 6-connected Zr6/Hf6 node were able to identify a significantly enhanced yield in Br?nsted acid catalyzed reactions under conventional heating and microwave irradiation. In addition, the detailed mechanism of active sites of the ring opening acylation reaction was confirmed by employing of density functional theory (DFT) calculations.

Ligand-promoted, copper nanoparticles catalyzed one-pot synthesis of substituted benzoxazoles from 2-bromoanilines and acyl chlorides

A facile, highly efficient, and practical one-pot synthetic strategy for benzoxazoles was developed by using copper nanoparticles as a catalyst with o-bromoanilines and acyl chlorides as starting materials. With the promotion of 1,10-phenanthroline ligand, the copper nanoparticles catalyst showed highly catalytic activity under mild conditions. This methodology is tolerant of a wide variety of functional groups and gives good to excellent yields in most examples. Furthermore, the solid catalyst could be recovered and reused conveniently several times with satisfactory yields.

Direct transition-metal-free intramolecular C-O bond formation: Synthesis of benzoxazole derivatives

A direct base-mediated intramolecular carbon-oxygen bond formation has been developed without a transition-metal catalyst. In the presence of 2.0 equiv of K2CO3 in DMSO at 140 °C, the intramolecular cyclization of o-haloanilides affords benzoxazoles in high yields. A mechanism via an initial formation of a benzyne intermediate followed by nucleophilic addition to form the C-O bond has been proposed.

Reactions of α,N-Diarylnitrones with O-Methyl Diphenylphosphinothioate and Oxidations of N-Alkylidene-2-hydroxyanilines with Silver Oxide. Preparation of Benzoxazoles

Reactions of α,N-diarylnitrones in the presence of O-methyl diphenylphosphinothioate at 150 deg C gave 2-arylbenzoxazoles (3) in fairly good yields.Oxidation of N-alkylidene-2-hydroxyanilines with silver oxide afforded 2-alkenyl-, 2-alkyl-, or 2-arylbenzoxazoles (7 and 3) in good yields under mild reaction conditions (at room temperature).A plausible mechanism for formation of 3 and 7 has been discussed briefly.