37069-08-2

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Benzooxazol-2-yl-phenyl)-ethanone is used as a key intermediate in the synthesis of pharmaceuticals for its potential anti-inflammatory and anti-cancer properties. It contributes to the development of new drugs that can help in the treatment of various diseases.
Used in Agrochemical Industry:
In the agrochemical industry, 1-(4-Benzooxazol-2-yl-phenyl)-ethanone is used as a building block for the creation of new agrochemicals. Its synthesis capabilities allow for the development of innovative products that can enhance crop protection and yield.
Used in Specialty Chemicals:
1-(4-Benzooxazol-2-yl-phenyl)-ethanone is utilized as a crucial component in the production of specialty chemicals. Its unique properties enable the creation of tailored chemical products for specific applications, such as dyes, pigments, and additives.
Used in Material Science:
1-(4-BENZOOXAZOL-2-YL-PHENYL)-ETHANONE is also used as a component in the development of new materials and polymers. Its integration into the field of material science allows for the creation of advanced materials with improved properties, such as enhanced strength, durability, or chemical resistance.
Overall, 1-(4-Benzooxazol-2-yl-phenyl)-ethanone is a versatile chemical compound with a wide range of applications across different industries, including pharmaceuticals, agrochemicals, specialty chemicals, and material science. Its potential biological activities and its role in the synthesis of various organic compounds make it a valuable asset in the ongoing research and development efforts in these fields.

Upstream product

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Relevant academic research and scientific papers

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling

Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper–aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.

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.

Direct C—H Bond Activation of Benzoxazole and Benzothiazole with Aryl Bromides Catalyzed by Palladium(II)-N-heterocyclic Carbene Complexes

Herein, we report that a series of novel palladium(II)-NHC complexes (NHC=N-heterocyclic carbene) were synthesized. The structures of all novel complexes were characterized by 1H NMR, 13C NMR, FT-IR spectroscopy and elemental analysis techniques. These palladium(II)-NHC complexes were tested as efficient catalysts in the direct C—H bond activation of benzoxazole and benzothiazole with aryl bromides in the presence of 1 mol% catalyst loading at 150 °C for 4 h. Under the given conditions, various aryl bromides were successfully applied as the arylating reagents to achieve the 2-arylbenzoxazoles and 2-arylbenzothiazoles in acceptable to high yields.

BTK INHIBITOR

Provided are a series of BTK inhibitors, and specifically disclosed are a compound, pharmaceutically acceptable salt thereof, tautomer thereof or prodrug thereof represented by formula (I), (II), (III) or (IV).

High-Throughput Screening Protocol for the Coupling Reactions of Aryl Halides Using a Colorimetric Chemosensor for Halide Ions

Mercury complex of 4-(2-pyridylazo)resorcinol (PAR-2Hg2+), a halide-ion chemosensor, was prepared and its efficiency as a tool for high-throughput screening (HTS) of transition-metal-catalyzed coupling reactions was investigated. It showed a high selectivity for halide ions. When the PAR-2Hg2+ complex was used in the Suzuki coupling reaction and C-H activated coupling reaction with aryl bromides, the quantitative and qualitative conversions of aryl halides were obtained from the reaction mixture color change.

Ligand-free direct C-arylation of heterocycles with aryl halides over a metal-organic framework Cu2(BPDC)2(BPY) as an efficient and robust heterogeneous catalyst

A crystalline porous metal-organic framework Cu2(BPDC) 2(BPY) was synthesized and characterized by X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), atomic absorption spectrophotometry (AAS), hydrogen temperature-programmed reduction (H2-TPR), and nitrogen physisorption measurements. The Cu2(BPDC)2(BPY) exhibited high catalytic activity in direct CH arylation reactions between heterocyles and aryl halides. The Cu 2(BPDC)2(BPY)-catalyzed CH arylation reaction could proceed to higher conversion than that of the reaction using Cu 3(BTC)2, Cu(BDC), Cu(BPDC), and Cu2(BDC) 2(BPY) as catalyst. Furthermore, under our conditions, the Cu 2(BPDC)2(BPY) also exhibited significantly higher activity than that of common copper salts, including Cu(NO3)2, CuCl, CuCl2, and CuI. Excellent reusability of the Cu-MOF in the direct heterocycle CH arylation reaction was achieved.

Palladium-catalyzed desulfitative C-arylation of a benzo[d]oxazole C-H bond with arene sulfonyl chlorides

A palladium-catalyzed direct desulfitative C-arylation of a benzo[d]oxazole C-H bond with arene sulfonyl chlorides is described. The procedure tolerates halo, cyano, nitro, trifluoromethyl, acetyl and acetylamino groups on the phenyl ring of sulfonyl chlorides, providing the arylation products in moderate to good yields. It represents a practical and attractive alternative for the synthesis of 2-aryl benzoxazoles.

Direct transition-metal-free intramolecular C-O bond formation: Synthesis of benzoxazole derivatives

A direct base-mediated intramolecular carbon-oxygen bond formation has been developed without a transition-metal catalyst. In the presence of 2.0 equiv of K2CO3 in DMSO at 140 °C, the intramolecular cyclization of o-haloanilides affords benzoxazoles in high yields. A mechanism via an initial formation of a benzyne intermediate followed by nucleophilic addition to form the C-O bond has been proposed.

Carbonates: Eco-friendly solvents for palladium-catalysed direct arylation of heteroaromatics

The palladium-catalysed direct 2-, 4- or 5-arylation of a wide range of heteroaromatics with aryl halides proceed in moderate to good yields using the eco-friendly solvents carbonates. The best yields were obtained using benzoxazole or thiazole derivatives. The arylation of furan, thiophene, pyrrole, imidazole or isoxazole derivatives was found to require a more elevated reaction temperature. The Royal Society of Chemistry 2010.

Direct arylation of oxazole and benzoxazole with aryl or heteroaryl halides using a palladium-diphosphine catalyst

Through the use of PdCl(dppb)(C3H5) as a catalyst, a range of aryl bromides and chlorides undergoes coupling via C-H bond activation/functionalization reaction with oxazole or benzoxazole in good yields. This air-stable catalyst can be used at low loadings with several substrates. Surprisingly, better results in terms of substrate/catalyst ratio were obtained in several cases using electron-excessive aryl bromides than with the electron-deficient ones. This seems to be mainly due to the relatively low thermal stability of some of the 2-arylbenzoxazoles formed with electron-deficient aryl halides. With these substrates, in order to obtain higher yields of product, the reactions had to be performed at a lower temperature (100-120 °C) using a larger amount of catalyst. On the other hand, in the presence of the most stable products, the reactions were performed at 150 °C using as little as 0.2 mol% catalyst. Arylation of benzoxazole with heteroaryl bromides also gave the coupling products in moderate to high yields using 0.2-5 mol% catalyst. With this catalyst, electron-deficient aryl chloride such as 4-chlorobenzonitrile, 4-chloroacetophenone or 2-chloronitrobenzene have also been used successfully.