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Upstream product

• 54367-80-5 7-chloro-3-p-tolyl-2⁽⁴⁾H-benzo[1,2,4]oxadiazine 
• 835-71-2 2-(4-methylphenyl)-1,3-benzoxazole 
• 99-94-5 p-Toluic acid 
• 95-55-6 2-amino-phenol 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 33667-89-9 N-(4-chlorophenyl)-4-methylbenzamide 
• 31928-44-6 2-bromo-4-chloroiodobenzene 
• 619-55-6 para-methylbenzamide 
• 36719-51-4 3,3-diethyl-1-(4-methylphenyl)-1-triazene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 104-87-0 4-methyl-benzaldehyde 
• 28443-50-7 2-amino-5-chlorophenol 

Relevant academic research and scientific papers

Copper-catalysed intramolecular O-arylation: A simple and efficient method for benzoxazole synthesis

A wide range of 2-substituted benzoxazoles can be efficiently synthesized from N-(2-iodo-/bromo-phenyl)benzamides, and even the less reactive N-(2-chlorophenyl)benzamides, via Cu-catalysed intramolecular coupling cyclization reactions using methyl 2-methoxybenzoate as the ligand under mild reaction conditions. In addition, the benzoxazoles can be easily prepared from the primary amides coupling with o-dihalobenzenes in a single step. This journal is

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.

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.

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.

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.

Mesoporous poly(melamine-formaldehyde): A green and recyclable heterogeneous organocatalyst for the synthesis of benzoxazoles and benzothiazoles using dioxygen as oxidant

A simple, highly efficient, and sustainable strategy for the synthesis of benzoxazole and benzothiazole derivatives was developed by using inexpensive, green, readily available, and recyclable mesoporous poly(melamine-formaldehyde) as a green, heterogeneous organocatalyst. The corresponding substituted benzoxazoles and benzothiazoles were obtained in good to excellent yields by aerobic oxidation of o-substituted aminobenzenes with various aldehydes under dioxygen atmosphere. The catalyst can be completely recovered through simple filtration to be reused more than six times without significant loss of catalytic activity.

Magnetically recoverable and reusable CuFe2O4 nanoparticle-catalyzed synthesis of benzoxazoles, benzothiazoles and benzimidazoles using dioxygen as oxidant

A green and efficient strategy for the synthesis of benzoxazoles, benzothiazoles and benzimidazoles has been developed by using inexpensive, readily available, dioxygen-stable and recyclable CuFe2O4 as the nanocatalyst, and o-substituted aminobenzene and various aldehydes as the starting materials. The CuFe2O4 nanoparticles are dioxygen insensitive and easily recoverable with an external magnet from the reaction medium. The catalyst can be reused ten times without significant loss of catalytic activity. This journal is the Partner Organisations 2014.

A highly efficient palladium-catalyzed desulfitative arylation of azoles with sodium arylsulfinates

A highly efficient palladium-catalyzed direct desulfitative arylation of azoles at C2-position has been developed using sodium arylsulfinates as aryl sources. Azoles including benzoxazoles, benzothiazoles, oxazoles, thiazoles, and 1,3,4-oxadiazoles reacted with sodium arylsulfinates smoothly to generate the corresponding products in good to excellent yields, and various substitution patterns were tolerated toward the reaction.

Chlorination and ortho-acetoxylation of 2-arylbenzoxazoles

Efficient and facile catalytic protocols for chlorination and ligand-directed ortho-acetoxylation of 2-arylbenzoxazoles have been developed. The chlorination is not a ligand-directed ortho-functionalization, but an electrophilic substitution process in the benzo ring of the benzoxazole moiety. Meanwhile, the acetoxylation exhibited high regioselectivity for the substrates containing a meta-substituent and occurred at the less sterically hindered ortho-C-H bond of the directing group. The Royal Society of Chemistry 2011.