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

• 119-33-5 4-methyl-2-nitrophenol 
• 104-87-0 4-methyl-benzaldehyde 
• 910470-93-8 (E)-4-methyl-2-((4-methylbenzylidene)amino)phenol 
• 95-84-1 3-amino-4-hydroxytoluene 
• 874-60-2 4-methyl-benzoyl chloride 
• 104-84-7 para-methylbenzylamine 
• 10531-78-9 5-methyl-1,3-benzoxazole 
• 1139705-26-2 4-methylphenyl imidazolesulfonate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 16308-16-0 1-(diacetoxyiodo)-4-methylbenzene 
• 624-31-7 4-tolyl iodide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-88-3 toluene 

Downstream Products

• 10165-24-9 5-methyl-2-(4-trans-styryl-phenyl)-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 
• 65203-90-9 2-{4-[4-(5-chloro-2-phenyl-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 
• 65203-99-8 2-{4-[4-(2,5-diphenyl-2H-[1,2,3]triazol-4-yl)-styryl]-phenyl}-5-methyl-benzooxazole 
• 65204-24-2 2-{4-[4-(4,5-diphenyl-[1,2,3]triazol-2-yl)-styryl]-phenyl}-5-methyl-benzooxazole 
• 72093-85-7 5-methyl-2-{4-[4-(3-phenyl-[1,2,4]oxadiazol-5-yl)-styryl]-phenyl}-benzooxazole 
• 72093-57-3 5-methyl-2-{4-[4-(5-phenyl-[1,2,4]oxadiazol-3-yl)-trans-styryl]-phenyl}-benzooxazole 
• 72093-69-7 2-(4-{4-[5-(4-chloro-phenyl)-[1,2,4]oxadiazol-3-yl]-trans-styryl}-phenyl)-5-methyl-benzooxazole 
• 72093-87-9 2-(4-{4-[3-(4-methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-trans-styryl}-phenyl)-5-methyl-benzooxazole 
• 72093-73-3 2-(4-{4-[5-(4-methoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-trans-styryl}-phenyl)-5-methyl-benzooxazole 
• 53349-52-3 5-methyl-2-{4-[trans-2-(2-phenyl-benzofuran-6-yl)-vinyl]-phenyl}-benzooxazole 
• 16143-16-1 2-[4-(trans-2-biphenyl-4-yl-vinyl)-phenyl]-5-methyl-benzooxazole 
• 53349-46-5 5-methyl-2-[4-(4-trans-styryl-trans-styryl)-phenyl]-benzooxazole 

Relevant academic research and scientific papers

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.

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.

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.

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.

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.

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.

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.

Ni-Catalyzed C?F Bond Functionalization of Unactivated Aryl Fluorides and Corresponding Coupling with Oxazoles

A Ni-catalyzed C?F bond functionalization of unactivated aryl fluorides with oxazoles as coupling partners was developed. Various arylated oxazoles could be obtained in moderate to good yields in the presence of Ni(cod)2/IMes catalytic system.

Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes

A novel and efficient methodology for the arylation of benzoxazoles with aromatic aldehydes catalyzed by deep eutectic solvent has been developed. The reaction smoothly proceeded with a wide range of substrates to give the desired products in high yields within short reaction time. Deep eutectic solvents are easily recovered and reused without significant loss of catalytic activity.