16155-95-6

Upstream product

• 2835-98-5 2-Hydroxy-4-methylanilin 
• 104-85-8 para-methylbenzonitrile 
• 16308-16-0 1-(diacetoxyiodo)-4-methylbenzene 
• 10531-80-3 6-methyl-1,3-benzoxazole 
• 104-87-0 4-methyl-benzaldehyde 
• 303793-19-3 N-(2-bromo-4-methylphenyl)-4-methylbenzamide 
• 583-68-6 2-bromo-p-toluidine 
• 874-60-2 4-methyl-benzoyl chloride 
• 106-38-7 para-bromotoluene 
• 36719-51-4 3,3-diethyl-1-(4-methylphenyl)-1-triazene 
• 106-49-0 p-toluidine 
• 71838-16-9 3-bromo-4-iodotoluene 
• 619-55-6 para-methylbenzamide 
• 122-00-9 para-methylacetophenone 

Downstream Products

• 72093-58-4 6-methyl-2-{4-[4-(5-phenyl-[1,2,4]oxadiazol-3-yl)-trans-styryl]-phenyl}-benzooxazole 
• 53349-60-3 6-methyl-2-{4-[trans-2-(2-phenyl-benzofuran-6-yl)-vinyl]-phenyl}-benzooxazole 
• 16253-68-2 2-[4-(trans-2-biphenyl-4-yl-vinyl)-phenyl]-6-methyl-benzooxazole 
• 14016-18-3 6-methyl-2-(4-trans-styryl-phenyl)-benzooxazole 
• 16178-05-5 6-trans-styryl-2-(4-trans-styryl-phenyl)-benzooxazole 
• 37431-00-8 2-{4-[4-(6-methyl-benzooxazol-2-yl)-trans-styryl]-phenyl}-7-phenyl-2,7-dihydro-benzo[1,2-d;3,4-d']bis[1,2,3]triazole 
• 53349-56-7 6-methyl-2-[4-(4-trans-styryl-trans-styryl)-phenyl]-benzooxazole 
• 59098-12-3 6-methyl-2-{4-[2-(5-methyl-2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-benzooxazole 
• 59098-38-3 2-(4-{2-[2-(4-chloro-phenyl)-5-methyl-2H-[1,2,3]triazol-4-yl]-vinyl}-phenyl)-6-methyl-benzooxazole 
• 59136-15-1 2-(4-{2-[2-(4-methoxy-phenyl)-2H-[1,2,3]triazol-4-yl]-vinyl}-phenyl)-6-methyl-benzooxazole 
• 59098-43-0 2-{4-[2-(2,5-diphenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-6-methyl-benzooxazole 
• 59098-49-6 2-(4-{2-[2-(4-chloro-phenyl)-5-phenyl-2H-[1,2,3]triazol-4-yl]-vinyl}-phenyl)-6-methyl-benzooxazole 
• 65203-91-0 2-{4-[4-(5-chloro-2-phenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-6-methyl-benzooxazole 
• 65205-61-0 2-{4-[4-(4-chloro-5-phenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-6-methyl-benzooxazole 

Relevant academic research and scientific papers

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.

Pyrazole-3-carboxylates assisted N-heterocyclic carbene palladium complexes: synthesis, characterization, and catalytic activities towards arylation of azoles with arylsulfonyl hydrazides

Four mononuclear and dinuclear pyrazole-3-carboxylates assisted NHC–Pd complexes have been synthesized and characterized. Notably, the bridge-cleavage reactions of [Pd(μ-Cl)(Cl)(NHC)]2 with 1H-pyrazole-3-carboxylic acid afforded dinuclear complexes [(NHC)Pd(μ-1H-pyrazolato-3-carboxylate)]2, in which the 1H-pyrazolato-3-carboxylate was employed as a N^N^O dianionic chelating and bridging ligand. To further explore the structural features and catalytic properties of the complexes, 1-methyl-1H-pyrazole-3-carboxylic acid was introduced into the coordination with [Pd(μ-Cl)(Cl)(NHC)]2 and the corresponding mononuclear complexes (NHC)PdCl(1-methyl-1H-pyrazole-3-carboxylate) were obtained. The catalytic properties of the complexes in desulfitative arylation of azoles with arylsulfonyl hydrazides were initially investigated.

Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes

A highly efficient palladium-catalyzed arylation of azoles at the C2-position using 1-aryltriazenes as aryl reagents was developed. Azoles including oxazoles, thiazoles, imidazoles, 1,3,4-oxadiazoles, and oxazolines could react with 1-aryltriazenes smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

Mixed N-heterocycles/N-heterocyclic carbene palladium(II) allyl complexes as precatalysts for direct arylation of azoles with aryl bromides

A series of mixed N-heterocycles/N-heterocyclic carbene palladium(II) allyl complexes with general formula [(NHC)Pd(η3-allyl)]2(μ2-N-heterocycles)(BF4)2 were prepared in one pot based on anion metathesis of (NHC)Pd(η3-allyl)Cl complexes and then ligand replacement with N-heterocycles [N-heterocycles = pyrazine (pyz), 4,4′-bipyridine (bpy) and trans-4,4′-bipyridylethylene (bpe)]. The solid-state structures shown dinuclear structures with two palladium(II) centers holding together by bridged N-heterocycles. Initially investigation of the obtained complexes as precatalysts for direct C[sbnd]H bond arylation of azoles with aryl bromides was carried out.

Preparation method of 2-phenylbenzoxazole compound

The invention relates to a preparation method of a 2-phenylbenzoxazole compound, comprising the following steps: (1) condensation reaction: a 2-amino phenol compound and a benzoyl chloride compound, which are used as raw materials, react in an organic solvent to obtain a condensation reaction solution; and (2) cyclization reaction: as a cyclization catalyst, acid is added into the condensation reaction solution to carry out a cyclization reaction at a certain temperature so as to obtain a cyclization reaction solution; after the reaction, an organic solvent is added for heating refluxing; andcooling filtration or liquid-separation condensation is finally carried out to obtain a 2-phenylbenzoxazole compound. The technology is simple; product post-treatment is simple; environmental pollution is less; the prepared 2-phenylbenzoxazole compound has high product quality and good stability; in addition to general use purpose, the prepared product also can be used for preparation of a high-end luminescent material; and the preparation method is a method suitable for industrial preparation.

A benzoxazole for the arylation method (by machine translation)

The invention relates to a benzoxazole for the arylation method, comprises the following steps: under the protection of the inert gas, the benzoxazole, aryl/heteroaryl tosylates, catalyst nitrogen heterocyclic carbene - palladium complex, alkaline material, reaction solvent, in the 80 - 150 °C reaction 12 - 24 H of the reaction liquid obtained, then processing reaction liquid to obtain product, to obtain 2 - aryl benzoxazole. The invention discloses a benzoxazole for the arylation method development of novel catalytic system, catalyst stability, is easy to obtain, can make the stable, low price of the aryl/heteroaryl tosylates participate in the reaction, reaction operation is simple, low cost, product yield and purity and the like, has good value for research and industrial application produces the scenery. (by machine translation)

Synthesis of N-heterocyclic carbene-PdCl-[(2-Pyridyl)alkyl carboxylate] complexes and their catalytic activities towards arylation of (benzo)oxazoles with aryl bromides

Four well-defined N-heterocyclic carbene-PdCl-[(2-Pyridyl)alkyl carboxylate] complexes have been conveniently synthesized through bridge-cleavage reactions of [Pd(μ-Cl)(Cl)(NHC)]2 with (2-pyridyl)alkyl carboxylic acids [2-(pyridin-2-yl)acetic acid and 3-(pyridin-2-yl)propanoic acid]. The new complexes have been fully characterized by NMR, elemental analysis, HR-MS and X-ray single-crystal diffraction. The catalytic performance of the complexes was screened and the obtained palladium (II) complexes shown effective catalytic activities for direct arylation of (benzo)oxazoles with aryl bromides. Moreover, the 2-(pyridin-2-yl)acetate stabilized NHC–Pd complexes were more efficient than the 3-(pyridin-2-yl)propanoate stabilized NHC–Pd analogues. Further studies exhibited that 2-(pyridin-2-yl)acetate, as ancillary ligand, could easily decarboxylate and transform into 2-methylpyridine in the reaction condition.

Synthesis of benzoxazoles via an iron-catalyzed domino C-N/C-O cross-coupling reaction

An eco-friendly and efficient method has been developed for the synthesis of 2-arylbenzoxazoles via a domino iron-catalyzed C-N/C-O cross-coupling reaction. Some of the issues typically encountered during the synthesis of 2-arylbenzoxazoles in the presence of palladium and copper catalysts, including poor substrate scope and long reaction times have been addressed using this newly developed iron-catalyzed method.

Containing heteroaryl chelating nitrogen heterocyclic cabeen arrowhead compound and its preparation method

The invention belongs to the field of organic compound synthesis and discloses a chelate-type N-heterocyclic carbene palladium compound containing heteroaromatic groups, and a synthetic and immobilization method thereof. The general formula of the compound is represented as follows. In the invention, with a polyfunctional compound amino alcohol as an initial raw material, a cyclization reaction and a condensation reaction are carried out to prepare an imidazole derivative of which an N-substituent group contains hydroxyl groups. The derivative then is subjected to an ionization reaction with a hetero-aromatic hydrocarbon halogenate to obtain a hetero-aromatic and hydroxyl groups di-substituted imidazolium salt. The imidazolium salt is further subjected to a metallization reaction to obtain an NHC-N chelate-type palladium compound. The compound has the activity of a homogeneous-phase N-heterocyclic carbene palladium catalyst, is simple in synthetic method, is high in yield, is easy to separate and is recyclable in catalysis of a C-H activating reaction, is greatly reduced in use cost and has a good application prospect in the field of catalysis.

Iron-catalyzed 2 - benzenes and wicked zuozuo apperception for the synthesis of the new method

The invention discloses a new synthesis method of iron-catalyzed 2-aryl benzoxazoles, which is prepared by directly performing C-N coupling and C-O coupling on benzamide and o-bromoiodobenzene serving as raw materials at a certain temperature in the presence an iron salt, a ligand and an alkali. According to the invention, a biological metal iron is introduced in synthesis of medical skeletons 2-aryl benzoxazoles, thus use of high-toxicity metals like palladium is avoided, and the application range of the method is expanded to substrates containing different substituent groups. The invention also successfully develops a catalyzing system which can have a catalysis effect on C-N and C-O coupling at the same time, and can greatly improve the safety of 2-aryl benzoxazoles in the synthesis process.