2008-07-3

Usage

InChI:InChI=1/C14H11NO/c1-2-6-11(7-3-1)10-14-15-12-8-4-5-9-13(12)16-14/h1-9H,10H2

Upstream product

• 140-29-4 phenylacetonitrile 
• 95-55-6 2-amino-phenol 
• 103-82-2 phenylacetic acid 
• 5442-34-2 ethyl 2-phenylacetimidate hydrochloride 
• 103-80-0 phenylacetyl chloride 
• 60-12-8 2-phenylethanol 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 273-53-0 benzoxazole 
• 884-90-2 benzyl diethyl phosphate 
• 13326-10-8 benzyl methyl carbonate 
• 7436-90-0 2,2-dibromostyrene 
• 108-86-1 bromobenzene 
• 1251919-71-7 sodium 2-(benzo[d]oxazol-2-yl)acetate 
• 24265-30-3 2-nitrophenyl phenylacetate 

Downstream Products

• 77036-86-3 (E)-2-(1,2-diphenylvinyl)benzo[d]oxazole 
• 38285-62-0 3-hydroxy-2,4-diphenyl-benzo[4,5]oxazolo[3,2-a]pyridin-1-one 
• 33442-81-8 6'-methoxy-3-methyl-8'-nitro-3'-phenyl-3H-spiro[benzooxazole-2,2'-chromene] 
• 38285-63-1 2-benzyl-3-hydroxy-4-phenyl-benzo[4,5]oxazolo[3,2-a]pyridin-1-one 
• 33442-79-4 3-methyl-6'-nitro-3'-phenyl-3H-spiro[benzooxazole-2,2'-chromene] 
• 33442-80-7 8'-methoxy-3-methyl-6'-nitro-3'-phenyl-3H-spiro[benzooxazole-2,2'-chromene] 
• 85678-61-1 C₂₉H₂₂N₂O₂ 
• 85678-73-5 2-(3-Benzothiazol-2-yl-1,2-diphenyl-propyl)-benzooxazole 
• 343233-19-2 4-Benzooxazol-2-yl-3-methyl-4-phenyl-butyronitrile 
• 74655-80-4 4-Benzooxazol-2-yl-3,4-diphenyl-butyronitrile 
• 343800-79-3 4-Benzooxazol-2-yl-3,4-diphenyl-butyric acid ethyl ester 
• 343820-50-8 3-(Benzooxazol-2-yl-phenyl-methyl)-cyclohexanone 
• 96549-26-7 N-(di-2-methyl-2-propenyl)phenylmethyl-o-aminophenol 
• 61799-53-9 4-methyl-1-phenyl-4-penten-2-one 

Relevant academic research and scientific papers

Aggregation induced emission (AIE) active β-ketoiminate boron complexes: Synthesis, photophysical and electrochemical properties

New keto-enol tautomeric benzoxazolyl and benzthiazolyl-1,2-diaryl β-ketoiminate based organoboron complexes have been synthesised and their fluorescence properties investigated. Boron complexes are widely known for their fluorescent properties, here we have synthesized organoboron complexes that show bright fluorescence in solid state and hardly any fluoresce in solution. These compounds exhibit aggregation induced emission (AIE) activity. Density functional theory (DFT) was employed for geometry optimisation and molecular orbital distribution computations in the ground state of the molecules. Electrochemical study demonstrates that these molecules possess high electron affinities as compared to the current electroluminescent materials like tris(8-hydroxyquinoli- nato)-aluminium (Alq3) and BODIPY, indicating the prospects of these boron complexes as an cient emitters in the optoelectronics.

Asymmetric Alkyl and Aryl/Azolation of Alkenes via a Single Cu(I) Complex

The copper-catalyzed, highly enantioselective alkyl and aryl/azolation of alkenes is reported. The employment of the chiral carbazole-based bisoxazoline (Cbzbox) ligand is critical to the success of this chemistry. Anionic tridentate ligands improve the reducibility of copper complexes, facilitating alkyl/aryl radical generation and providing good enantiocontrol in the azolation. The three-component coupling reactions feature mild reaction conditions and tolerate broad range of functional groups. This strategy allows straightforward introduction of valuable azole functionalities into a elaborated molecular system through direct C-H functionalization.

Cu-catalyzed Asymmetric Dearomative [3 + 2] Cycloaddition Reaction of Benzazoles with Aminocyclopropanes

The enantioselective dearomative [3 + 2] cycloaddition reaction of benzazoles with aminocyclopropanes has been successfully developed. In the presence of a copper complex, derived from Cu(OTf)2 and bisoxazoline, a series of hydropyrrolo-benzazole derivatives containing quaternary stereogenic centers were obtained in high yields with excellent enantioselectivity. This method could also provide 2-amino cyclopropanes with high enantiomeric purity by an efficient kinetic resolution. In addition, products could be transformed to pyrrolo-benzothiazines and 1,5-benzothiazepines. Chiral compounds are of great significance in many areas given that two corresponding enantiomers could have completely different properties in chiral environments. Therefore, technologies used to produce chiral compounds in their enantiopure form are particularly attractive and highly desirable. Catalytic asymmetric dearomatization reactions have become efficient methods for the construction of chiral fused- or spiro-heterocycles from simple aromatics. Polyheterocyclic structures containing a hydropyrrolo-azole motif are found extensively in natural products and biologically active compounds. Therefore, efficient methods for constructing complex chiral hydropyrrolo-azole compounds will benefit the lead identification in drug discovery. Herein, we report the highly enantioselective construction of hydropyrrolo-benzazoles via copper-catalyzed dearomative [3 + 2] cycloaddition of benzazoles with donor-acceptor aminocyclopropanes. Heterocycles are a very important class of compounds that exist extensively as structural cores in natural products and biologically active molecules. Catalytic asymmetric dearomatization (CADA) is an efficient strategy for the construction of chiral fused- or spiro-heterocycles from simple planar aromatic compounds. Herein, we report the development of enantioselective dearomative [3 + 2] cycloaddition reactions of benzazoles with aminocyclopropanes via kinetic resolution. In the presence of a copper complex, derived from Cu(OTf)2 and bisoxazoline, a series of hydropyrrolo-benzazole derivatives containing quaternary stereogenic centers were obtained in high yields (up to 99%) with excellent enantioselectivity (up to 99% enantiomeric excess [ee]). With the same catalytic system, 2-amino cyclopropane-1,1-dicarboxylates with a high enantiomeric purity (up to 98% ee) were also obtained by an efficient kinetic resolution (s values of up to 95). In addition, the utility of this method was showcased by the facile transformation of products into several important heterocyclic frameworks, including pyrrolo-benzothiazine and 1,5-benzothiazepine.

Break-and-Build Strategy for the Synthesis of 2-Benzoylbenzoxazoles from o-Aminophenols and Acetophenones

Although compounds with a 2-benzoylbenzoxazole motif are biologically relevant, there are only a few methods for synthesizing them, most of which relied on multistep process or required substrates bearing activating groups. Herein, we report an efficient method for the synthesis of such compounds by direct reactions of o-aminophenols with acetophenones promoted by sulfur in DMSO. The reaction was found to proceed via a Willgerodt rearrangement-type benzoxazolation of acetophenones followed by a benzylic oxidation to reinstall the carbonyl function. This method has a broad substrate scope and good tolerance for sensitive functional groups. (Figure presented.).

Elemental Sulfur-Promoted Benzoxazole/Benzothiazole Formation Using a C=C Double Bond as a One-Carbon Donator

An efficient method to assemble diverse benzoxazoles/benzothiazoles in good yields was developed via oxidative cyclization with 2-aminothiophenols or 2-iodoanilines as raw materials. In this protocol, elemental sulfur was used as the effective oxidant and C atoms on the C=C double bond were introduced as a one-carbon donator.

Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands

Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.

Iron-Catalyzed Sulfur-Promoted Decyanative Redox Condensation of o-Nitrophenols and Arylacetonitriles: An Unprecedented Route to 2-Arylbenzoxazoles

Elemental sulfur in the presence of a catalytic amount of FeCl2·4H2O was found to be highly efficient for the promotion of decyanative redox condensation reactions of o-nitrophenols with arylacetonitriles, to give a wide range of 2-arylbenzoxazoles. The utility of elemental sulfur was highlighted by its role as cyanide scavenger and external reducing agent.

Elemental Sulfur-Promoted Oxidative Rearranging Coupling between o-Aminophenols and Ketones: A Synthesis of 2-Alkyl benzoxazoles under Mild Conditions

In the presence of N-methylpiperidine, elemental sulfur was found to act as excellent oxidant in promoting oxidative rearranging coupling between o-aminophenols and ketones. A wide range of 2-alkylbenzoxazoles was obtained under mild conditions.

2-substituted benzoxazole preparation method of compound

The invention relates to a preparing method of 2-substituted benzoxazole compounds. The compounds are obtained by reaction of products obtained by reaction of acyl chloride and o-nitrophenol or derivatives thereof under catalyzing of reducing agent ammonium formate, a solvent and palladium-containing agents. According to the method, the reaction condition is mild, environment is protected, raw materials are rich and easy to obtain, operation is easy, yield is high, and various kinds of performance are optimized.

Exploration of 2-benzylbenzimidazole scaffold as novel inhibitor of NF-κB

For finding the novel inhibitor of nuclear factor κB activity, a series of benzimidazole derivatives were rationally designed, synthesized and systematically studied for their in vitro activities against LPS induced NF-κB inhibition in RAW 264.7 cells using the SEAP assay based on the flexible chalcone JSH ((E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4-hydroxy phenyl)prop-2-en-1-one) which was previously reported. Although most of the benzimidazole derivatives showed strong inhibitory activity in low micromolar potency, 2-(4-methoxybenzyl)-1H-benzo[d]imidazole (3m; IC50 = 1.7 μM) and 2-(2-methoxybenzyl)-1H-benzo[d]imidazole (3n; IC50 = 2.4 μM) showed the best inhibition. The structure activity relationship revealed that 2-benzylbenzimidazole scaffold with hydrogen bonding acceptor on phenyl ring appears as a pharmacophore.