77791-12-9

Upstream product

• 17646-94-5 benzoic acid-(2-hydroxy-4-methoxy-anilide) 
• 77791-10-7 N-(2-chloro-4-methoxyphenyl)benzamide 
• 98-88-4 benzoyl chloride 
• 704-14-3 3-methoxy-6-nitro-phenol 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 845266-67-3 2-[imino(phenyl)methyl]-5-methoxyphenol 
• 131-57-7 Benzophenone-3 
• 40925-70-0 2-amino-5-methoxyphenol 
• 108-88-3 toluene 
• 150-19-6 O-methylresorcine 
• 3848-27-9 benzaldehyde oxime benzoyl ester 
• 10365-98-7 3-methoxyphenylboronic acid 
• 51942-54-2 3-phenyl-4,4-dimethyl-5-oxo-2-isoxazoline 
• 932-90-1 Benzaldoxime 

Relevant academic research and scientific papers

Cu-Catalyzed Synthesis of Benzoxazole with Phenol and Cyclic Oxime

A Cu-catalyzed straightforward synthesis of benzoxazoles from free phenols and cyclic oxime esters is reported. The mild reaction conditions tolerate various electron-withdrawing and electron-donating functional groups on both substrates, affording benzoxazoles in moderate to good yields. With this protocol, large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps are demonstrated. A catalytic mechanism, which includes Cu-catalyzed amination via inner-sphere electron transfer and consequent annulation, is proposed.

Oxidative cyclization and synthesis of benzoxazole derivatives and hydrolytic phosphatase activity studies on dinuclear diphenoxo-bridged zinc(II)complexes

Diphenoxo bridged dinuclear zinc complexes, [Zn2(Phimp)2(Cl)2] (1) (PhimpH = (E)-2-((2-phenyl-2-(pyridin-2-yl)hydrazono)methyl)phenol), [Zn2(Me-Phimp)2(Cl)2] (2) (Me-PhimpH = (E)-4-methyl-2-((2-phenyl-2-(pyridin-2-yl)hydrazono)methyl)phenol), [Zn2(OMe-Phimp)2(Cl)2] (3) (OMe-PhimpH = (E)-4-methoxy-2-((2-phenyl-2-(pyridin-2-yl)hydrazono)methyl)phenol), were synthesized and spectroscopically characterized. The molecular structure of 2 was determined using X-ray crystallography. DFT and TD-DFT calculations were performed to optimize the molecular geometry, interpret the spectroscopic results and investigate the contribution of the ligands to the redox properties of the complexes. Phenoxyl radical complexes were generated in solution via chemical oxidation using ceric ammonium nitrate (CAN) and the redox properties were examined through cyclic voltammetric measurements. The hydrolysis of para-nitrophenylphosphate (PNPP) by all the dinuclear zinc complexes was investigated to mimic phosphatase activity. Catalytic oxidative cyclization by these complexes and synthesis of benzoxazole derivatives was investigated.

Iodine Promoted One-Pot Synthesis of 2-Aryl Benzoxazoles from Amidoximes via Oxidative Cyclization and Ring Contraction

A molecular I2-promoted one-pot synthesis of 2-aryl benzoxazoles has been developed by using amidoximes rather than the limited 2-aminophenols or 2-haloamides as substrates. The amidoxime substrates provided unique and efficient strategies for converting readily available aniline and benzaldehyde precursors into valuable chemicals. This transformation proceeded smoothly under transition-metal-free conditions through a sequential oxidative cyclization and ring contraction, and provided a potential route for introducing certain groups at any site of the scaffold.

Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions

The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.

Electrochemical synthesis of benzoxazoles from anilides-a new approach to employ amidyl radical intermediates

A novel electrochemical method for the synthesis of benzoxazoles from readily available anilides is reported. Various functionalities are tolerated and good yields can be achieved. By employing common electrode materials and a simple constant current protocol, this method is an attractive new alternative to conventional pathways.

Iron-catalyzed synthesis of benzoxazoles by oxidative coupling/cyclization of phenol derivatives with benzoyl aldehyde oximes

An iron-catalyzed oxidative coupling/cyclization reaction for the synthesis of benzoxazoles at room temperature is reported. This reaction was enabled by an inexpensive iron(iii) catalyst by treating readily available phenol derivatives with benzoyl aldehyde oximes. Mechanistic studies show that benzoyl aldehyde oxime is not only used as a substrate, but also serves as an ancillary ligand to support the iron salt in the promotion of the transformation.

Base-Free Selective O-Arylation and Sequential [3,3]-Rearrangement of Amidoximes with Diaryliodonium Salts: Synthesis of 2-Substituted Benzoxazoles

A variety of functionalized 2-substituted benzoxazoles can be prepared in good yields from amidoximes and diaryliodonium salts by selective O-arylation and sequential [3,3]-rearrangement under metal-free conditions. O-arylation of amidoximes was promoted by 3 ? molecule sieves in the absence of a base and a sequential TFA-mediated [3,3]-rearrangement was used to synthesize 2-substituted benzoxazoles. Both of the O-aryl products and rearrangement products were compatible with a broad range of sensitive functional groups such as ester, aldehyde, nitro, vinyl, amine, and amide groups in addition to halides. A bidentate N-ligand with double benzoxazoles was prepared at gram-scale in two steps. (Figure presented.).

Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement

A Beckmann-type rearrangement of o-hydroxy and o-aminoaryl N-H ketimines has been developed to prepare benzoxazoles and N-Ts benzimidazoles, respectively. The ketimine derivatives were easily prepared by condensation of ammonia with the corresponding ketones and (diacetoxyiodo)benzene was found to act as an efficient oxidant to trigger the [1,2]-aryl migration towards the formation of the desired heterocycles. Depending on the substitution pattern, the results revealed another mechanistic pathway through which benzisoxazoles or 1H-indazoles could be formed. The Beckmann-type rearrangement strategy was applied to the synthesis of benzimidazole-containing biorelevant targets such as chlormidazole and clemizole.

Organocatalytic syntheses of benzoxazoles and benzothiazoles using aryl iodide and oxone via C-H functionalization and C-O/S bond formation

An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.