57000-63-2

Usage

Type of compound

Aromatic heterocyclic compound

Oxazole family

Characterized by a five-membered ring containing one oxygen and one nitrogen atom

Substituents

3-chlorophenyl group and a phenyl group attached to the oxazole ring

Structural properties

Distinct structure due to the presence of the substituents

Chemical properties

Unique reactivity because of the substituents and oxazole ring

Applications

Organic synthesis, medicinal chemistry research, pharmaceutical development, biologically active compounds, agrochemicals, and material science.

Upstream product

• 5468-37-1 2-aminoacetophenone hydrochloride 
• 587-04-2 m-Chlorobenzaldehyde 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 4152-90-3 m-chlorobenzylamine 
• 1074-12-0 phenylglyoxal hydrate 
• 98-86-2 acetophenone 
• 618-48-4 3-chlorobenzamide 
• 122-78-1 phenylacetaldehyde 
• 38925-71-2 β-(m-chlorbenzamido)ethylbenzol 
• 536-74-3 phenylacetylene 
• 4070-53-5 3-chloro-N-hydroxybenzamide 
• 618-46-2 m-Chlorobenzoyl chloride 
• 22966-13-8 3-(3-chlorophenyl)-1-phenylprop-2-en-1-one 
• 34158-71-9 3-chlorobenzaldehyde oxime 

Relevant academic research and scientific papers

Synthesis of 2,5-disubstituted oxazoles: Via cobalt(III)-catalyzed cross-coupling of N -pivaloyloxyamides and alkynes

An efficient synthesis of 2,5-disubstituted oxazoles via Co(iii) catalysis is described herein. The synthesis is achieved under mild conditions through [3+2] cycloaddition of N-pivaloyloxyamides and alkynes. The reaction operates through an internal oxidation pathway and features a very broad substrate scope. The one-step synthesis of natural products such as texamine and balsoxin has been demonstrated via this protocol.

Metal-free iodine(iii)-promoted synthesis of 2,5-diaryloxazoles

A nonmetal-catalyzed oxidative cyclization to achieve 2,5-disubstituted oxazoles from inexpensive and readily available substituted chalcone, (diacetoxyiodo)benzene (PIDA) and ammonium acetate (NH4OAc) at room temperature is described. The reaction forms a variety of 2,5-diaryloxazoles in good to excellent yields with broad substrate scope under mild conditions without the requirement of ligands and additional bases.

N -Bromosuccinimide as a Brominating Agent for the Transformation of N -H (or N -Benzyl) Ketoaziridines into Oxazoles

A novel procedure for the direct synthesis of 2,5-diaryloxazoles starting from N-H ketoaziridines is described. The method proceeds via the in situ formation of N-bromoketoaziridines in the presence of N-bromosuccinimide followed by the generation of intermediate azomethine ylides. A plausible mechanism for this transformation is proposed.

Iodine catalysed intramolecular C(sp3)-H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides

Iodine catalyzed synthesis of 2,5-disubstituted oxazoles from N-arylethylamides through intramolecular C(sp3)-H functionalization under metal-free conditions is described. The method is tolerable to a wide range of substrates having a variety of functional groups with moderate to good yields of the products.

Convenient one-pot synthesis of 2,5-disubstituted oxazoles via a catalytic oxidative dehydrogenation of F3CSO3H·SiO 2-DDQ/CuCl2/LiCl

A facile one-pot synthesis of 2,5-disubstituted oxazoles was developed via cyclization of aldoximes and phenylacetylene then dehydrogenation oxidation. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was studied for the selective oxidation of oxazolines using Cu2+/Li+ as catalyst and O2 as indirect oxidant. The reaction results showed that this catalyst system can effectively catalyze the oxidation of oxazolines to the corresponding oxazoles. Thus, a variety of polysubstituted oxazoles was easily synthesized in high yields by catalytic oxidation of 2,3-dichloro-5,6-dicyano-1, 4-benzoquinone/CuCl2/LiCl/O2.

Metal-free dual sp3 C-H functionalization: I2- promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles

An I2-promoted sp3 C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C-H bond and the formation of C-N, C-O bonds.

Iodine(III)-promoted synthesis of oxazoles through oxidative cyclization of N -styrylbenzamides

The hypervalent iodine reagent PhI(OTf)2, generated in situ, has been successfully utilized in an intramolecular oxidative cyclization of N-styrylbenzamides. In remarkably short reaction times, the desired 2,5-disubstituted oxazoles were isolated in high yields in this metal-free oxidative C-O bond-forming reaction. Georg Thieme Verlag Stuttgart, New York.

Simple and efficient preparation of 2,5-disubstituted oxazoles via a metal-free-catalyzed cascade cyclization

A practical and simple synthesis of 2,5-disubstituted oxazoles was developed via an iodine-catalyzed tandem oxidative cyclization. A wide range of common commercial aromatic aldehydes can be used as reaction substrates, which displayed excellent functional group compatibility in this reaction.

TBHP/I2-mediated domino oxidative cyclization for one-pot synthesis of polysubstituted oxazoles

A facile type of one-pot, transition-metal-free domino process was developed for the synthesis of oxazoles. Thus, a variety of polysubstituted oxazoles were easily synthesized via t-BuOOH/I2-mediated domino oxidative cyclization from readily available starting materials under mild conditions.

2,5-SUBSTITUTED OXAZOLE DERIVATIVES AS PROTEIN KINASE INHIBITORS FOR THE TREATMENT OF CANCER

Certain oxazole-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, methods of using compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions comprising compounds exhibiting ATP-utilizing enzyme inhibitory activity, are disclosed.