16155-94-5

Usage

InChI:InChI=1/C15H13NO/c1-10-3-6-12(7-4-10)15-16-13-9-11(2)5-8-14(13)17-15/h3-9H,1-2H3

Upstream product

• 99-94-5 p-Toluic acid 
• 95-84-1 3-amino-4-hydroxytoluene 
• 10531-78-9 5-methyl-1,3-benzoxazole 
• 106-43-4 para-chlorotoluene 
• 106-49-0 p-toluidine 
• 36719-51-4 3,3-diethyl-1-(4-methylphenyl)-1-triazene 
• 766-97-2 4-n-methylphenylacetylene 
• 14939-05-0 1-phenyl-3-(4-methylphenyl)prop-2-yn-1-one 
• 106-38-7 para-bromotoluene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 352-32-9 p-fluorotoluene 
• 132680-48-9 O-4-methylphenyl N,N-diethylcarbamate 
• 17177-63-8 4-tolyl mesylate 
• 16156-59-5 phenyl methanesulfonate 

Downstream Products

• 59098-37-2 2-(4-{2-[2-(4-chloro-phenyl)-5-methyl-2H-[1,2,3]triazol-4-yl]-vinyl}-phenyl)-5-methyl-benzooxazole 
• 59098-29-2 2-(4-{2-[2-(4-methoxy-phenyl)-2H-[1,2,3]triazol-4-yl]-vinyl}-phenyl)-5-methyl-benzooxazole 
• 59098-42-9 2-{4-[2-(2,5-diphenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-5-methyl-benzooxazole 
• 65204-24-2 2-{4-[4-(4,5-diphenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-5-methyl-benzooxazole 
• 65203-99-8 2-{4-[4-(2,5-diphenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-5-methyl-benzooxazole 
• 65204-15-1 2-{4-[4-(4-chloro-5-phenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-5-methyl-benzooxazole 
• 65203-90-9 2-{4-[4-(5-chloro-2-phenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-5-methyl-benzooxazole 
• 59098-48-5 2-(4-{2-[2-(4-chloro-phenyl)-5-phenyl-2H-[1,2,3]triazol-4-yl]-vinyl}-phenyl)-5-methyl-benzooxazole 
• 59098-11-2 5-methyl-2-{4-[2-(5-methyl-2-phenyl-2H-[1,2,3]triazol-4-yl)-vinyl]-phenyl}-benzooxazole 
• 10165-24-9 5-methyl-2-(4-trans-styryl-phenyl)-benzooxazole 
• 71943-94-7 2-(4-{4-[4,5-dichloro-1-(4-chloro-phenyl)-1H-pyrazol-3-yl]-styryl}-phenyl)-5-methyl-benzooxazole 
• 71943-80-1 2-(4-{4-[1-(4-chloro-phenyl)-1H-pyrazol-3-yl]-styryl}-phenyl)-5-methyl-benzooxazole 
• 71943-86-7 2-{4-[4-(4-chloro-1-phenyl-1H-pyrazol-3-yl)-styryl]-phenyl}-5-methyl-benzooxazole 
• 71943-72-1 5-methyl-2-{4-[4-(1-phenyl-1H-pyrazol-3-yl)-styryl]-phenyl}-benzooxazole 

Relevant academic research and scientific papers

Stable Pd(0) Complexes with Ferrocene Bisphosphanes Bearing Phosphatrioxaadamantyl Substituents Efficiently Catalyze Selective C-H Arylation of Benzoxazoles by Aryl Chlorides

Versatile applications and unique performance of 1,1’-bis(diphenylphosphanyl)ferrocene (dppf) in coordination chemistry and catalysis prompted the search for its analogs. This contribution describes the synthesis of the first donor-unsymmetric dppf congeners bearing bulky and rigid 1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantyl (CgP) donor groups, viz. Ph2PfcPCg (1) and Ph2PfcCH2PCg (2; fc=ferrocene-1,1’-diyl). Bis-phosphanes 1 and 2 were converted into air-stable Pd(0) complexes, [Pd(ma)(L^L)] (L^L=1 and 2; ma=maleic anhydride). Together with [Pd(ma)(dppf)], these complexes were applied as catalysts in Pd-catalyzed C?H arylation of benzoxazoles with aryl chlorides in n-butanol as an environmentally benign solvent. Among all catalysts tested in this study, complex [Pd(ma)(2)] performed the best, providing a high-yield and selective synthesis of 2-arylbenzoxazoles from a range of the generally less reactive chloroarenes at low catalyst loading (typically 1 mol.%). Under similar conditions, the structurally related heterocycles (e. g., 1-methylbenzimidazole and benzothiazole) did not react.

Dowex 50W: A green mild reusable catalyst for the synthesis of 2-aryl benzoxazole derivatives in aqueous medium

In this work simple efficient, one pot and environmentally friendly method was developed for the synthesis of 2-Aryl-1H-benzoxazole derivatives at 80oC using ortho-aminophenol and various aldehydes. It has been found that Dowex 50W is an effective catalyst to prepare moderate to high yield of a variety of benzoxazole derivatives through a clean and simple process. Aqueous medium, green methodology, rapid reaction, reusability of heterogeneous catalyst are the great advantages of this protocol.

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.

Photoinduced Heterogeneous C?H Arylation by a Reusable Hybrid Copper Catalyst

Heterogeneous copper catalysis enabled photoinduced C?H arylations under exceedingly mild conditions at room temperature. The versatile hybrid copper catalyst provided step-economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS analysis of the hybrid copper catalyst, among others, supported its outstanding stability and reusability.

Sulfur/DABCO Promoted Reductive Coupling/Annulation Cascade Reaction between o -Hydroxy/Amino Nitrobenzenes and Benzaldehydes

Sulfur/DABCO was found to be an efficient reagent in promoting- the reductive coupling/annulation of o -nitrophenols or o -nitroanilines with benzaldehydes. This method represents a simple, straightforward, and green approach to the construction of benz-oxazoles and benzimidazoles.

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 the copper-catalyzed hydroamination of alkynones with 2-aminophenols

We describe herein the synthetic method to benzoxazole derivatives via the copper-catalyzed hydroamination of alkynones with 2-aminophenols. The method produced a wide variety of functionalized benzoxazole derivatives in good yields. Preliminary mechanistic experiments revealed that the reaction would proceed through the copper-catalyzed hydroamination of alkynones and the sequential intramolecular cyclization of β-iminoketones/elimination of acetophenone promoted by the copper catalyst.

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.

(N-heterocyclic carbene)PdCl(N-heterocyclic carboxylate) complexes: Synthesis and catalytic activities towards arylation of benzoxazoles with aryl halides

A series of N-heterocyclic carboxylate-stabilized N-heterocyclic carbene palladium complexes have been synthesized and fully characterized. The solid-state structures indicate that each of the palladium centers is coordinated by an N-heterocyclic carbene, a chloride and a bidentate N,O-donor N-heterocyclic carboxylate ligand. The catalytic performance of the complexes was screened and the results revealed that the complexes exhibit moderate to high catalytic activities for the direct C─H bond arylation of benzoxazoles with aryl bromides.