5014-83-5

Usage

Uses

Used in Organic Chemistry:
4,5-diphenyl-2(3H)-Oxazolone is used as a reagent in the synthesis of various organic compounds, particularly in the field of organic chemistry. Its unique structure and properties make it a valuable component in the creation of complex organic molecules.
Used in Fluorescent Compounds Production:
In the realm of fluorescent compounds, 4,5-diphenyl-2(3H)-Oxazolone is utilized for its ability to contribute to the development of materials that exhibit luminescent properties. These compounds have a wide range of applications, including in sensors, imaging, and as markers in biological research.
Used as a Stabilizer in Plastics Production:
4,5-diphenyl-2(3H)-Oxazolone also serves as a stabilizer in the production of plastics, enhancing their durability and resistance to degradation. This application is crucial for improving the longevity and performance of plastic materials in various industries.
Used in Pharmaceutical Research:
4,5-diphenyl-2(3H)-Oxazolone has been studied for its potential biological activities, including antibacterial and antifungal properties. This makes 4,5-diphenyl-2(3H)-Oxazolone a promising candidate for pharmaceutical research and development, particularly in the search for new antibiotics and antifungal agents to combat drug-resistant infections.
Overall, 4,5-diphenyl-2(3H)-Oxazolone is a multifaceted chemical with applications spanning across organic synthesis, material science, and pharmaceuticals, highlighting its importance in modern scientific and industrial endeavors.

InChI:InChI=1/C15H11NO2/c17-15-16-13(11-7-3-1-4-8-11)14(18-15)12-9-5-2-6-10-12/h1-10H,(H,16,17)

Upstream product

• 60-35-5 acetamide 
• 49656-04-4 2-Chlor-4,5-diphenyl-oxazol 
• 77287-34-4 formamide 
• 463-72-9 carbamic chloride 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 51-79-6 urethane 
• 57203-39-1 4,5-diphenyl-2-p-tolylsulfanyl-oxazole 
• 67322-93-4 2-dimethylcarbamoyloxy-4,5-diphenyl-oxazole 
• 4113-66-0 2-ethoxy-4,5-diphenyl-oxazole 
• 59749-82-5 1-tert-butyl-3-(2-oxo-1,2-diphenyl-ethyl)-urea 
• 61416-41-9 imidazole-1-carboxylic acid 2-oxo-1,2-diphenyl-ethylamide 
• 67322-94-5 (ethoxycarbonylamino)phenylmethyl phenyl ketone 
• 87696-41-1 4,5-diphenyl-2-<(4-pentenyl)oxy>oxazole 
• 87696-42-2 4,5-diphenyl-2-<(5-hexenyl)oxy>oxazole 

Downstream Products

• 53581-35-4 4,5-diphenyl-3-methyl-2-oxo-3H-1,3-oxazole 
• 110423-13-7 N-(α'-oxo-bibenzyl-α-yl)-valeramide 
• 62762-72-5 2-Phenyl-4-acetyl-2(3H)-oxazolone 
• 62762-73-6 3-benzyl-4,5-diphenyl-4-oxazolin-2-one 
• 67322-90-1 3-chloroacetyl-4,5-diphenyl-3H-oxazol-2-one 
• 68570-38-7 2-methoxy-4,5-diphenyl-oxazole 
• 6670-13-9 4,5-diphenyl-4-oxazolin-2-thione 
• 49656-04-4 2-Chlor-4,5-diphenyl-oxazol 
• 13342-55-7 5-[4-(4-bromo-benzoyl)-phenyl]-4-phenyl-3H-oxazol-2-one 
• 13342-60-4 5-[4-(3,4-dichloro-benzoyl)-phenyl]-4-phenyl-3H-oxazol-2-one 
• 53581-33-2 2-oxo-4,5-diphenyl-oxazole-3-carboxylic acid ethyl ester 
• 67322-91-2 3-benzoyl-4,5-diphenyl-3H-oxazol-2-one 
• 59167-72-5 2-oxo-4,5-diphenyl-oxazole-3-carboxylic acid anilide 
• 59167-70-3 2-oxo-4,5-diphenyl-oxazole-3-carboxylic acid methylamide 

Relevant academic research and scientific papers

(Enantio)selective Hydrogen Autotransfer: Ruthenium-Catalyzed Synthesis of Oxazolidin-2-ones from Urea and Diols

A novel strategy for the synthesis of oxazolidin-2-ones from vicinal diols and urea is described. In this heterocycle synthesis, two different C?O and C?N bonds are sequentially formed in a domino process consisting of nucleophilic substitution and alcohol amination. The use of readily available starting materials and the good atom economy render this process environmentally benign. While this transformation is already highly chemo- and regioselective, we also developed the first asymmetric version of this method using (R)-(+)-MeO-BIPHEP as the chiral ligand.

Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors

This invention is in the field of antiinflammatory pharmaceutical agents and specifically relates to compounds, compositions and methods for treating disorders mediated by cyclooxygenase-2 or 5-lipoxygenase, such as inflammation.

Substituted Oxazoles: Synthesis via Lithio Intermediates

Reactions of 2-α-, 2-, 4-, and 5-lithiooxazoles are used to prepare various substituted derivatives.Previously unrecognized time dependence for the reaction of a 2-lithiooxazole with benzaldhyde is described, and a rationale for this behavior is offered.Competitive reactions occur when the readily available 2,5-diphenyloxazole is treated with n-butyllithium.Deprotonation of the ortho position of the 2-phenyl group and addition of n-butyl to the 2-position of the oxazole compete with the desired 4-lithiation.The use of sec-butyllithium/catalytic lithium tetramethylpiperidide allows preferential formation of 4-lithio-2,5-diphenyloxazole.This intermediate has been converted to the 4-bromo, -methyl, -hydroxybenzyl, -benzoyl, and -trialkylsilyl derivatives.Lithiation of 2,4-diphenyloxazole and subsequent trimethylsilylation occur readily at the 5-position.Deprotonation of 2-alkyloxazoles occurs at the α-carbon in preference to ring sites.Further reaction of an α-phenyl-2-oxazolemethanol methoxymethyl ether with base and acetyl chloride leads to an acyloin derivative.Chromic acid oxidation is used to prepare both 2- and 4-benzoyloxazoles.The formation of an 2-ethoxyoxazole from 2-oxazolone vis Meerwein salt chemistry is described.

Synthesis of α,β-Epoxyacyl Azides and Their Rearrangement to Epoxy Isocyanates and 3- and 4-Oxazolin-2-ones

The conversion of α,β-epoxy carboxylates 6 into α,β-epoxyacyl azides 4 proceeds either via reaction of the mixed anhydrides 7 with sodium azide or via reaction of epoxyacyl chlorides 8 with hydrazoic acid-pyridine.The latter method is preferred.The azides 4 undergo a smooth thermal Curtius rearrangement to give 4-oxazolin-2-ones 10 for the substrates 4a-h having a hydrogen atom at C(β).Monitoring this reaction by means of IR shows that the epoxy isocyanates 5 are intermediates.Intramolecular ring expansion of 5 then leads to 3-oxazolin-2-ones 9 that tautomerizeto the 4-isomers 10a-h.Epoxyacyl azides 4i,n-q, having no hydrogen atom at C(β), producing 3-oxazolin-2-ones 9i,n-q by a proton shift is not possible.The products 9i and 9q rapidly add water at the imine bond to give oxazolidin-2-ones 11.Epoxy isocyanate 5k is reasonable stable in solution; reaction with methanol affords urethane 12.

Studies Dealing with the Aza-Claisen Rearrangement of 2-Allyloxy-Substituted Oxazoles

The scope of the thermal -sigmatropic rearrangement of a number of 2-allyloxy-substituted 4,5-diphenyloxazoles has been examined.These systems undergo a facile aza-Claisen rearrangement to give 3-allyl-substituted 4,5-diphenyl-4-oxazolin-2-ones.In contrast to the thermal results, irradiation of the 2-allyloxy- or benzyloxy-substituted oxazole gave rise to a mixture of 3- and 5-substituted oxazolinones.The photolysis proceeds via C-O bond scission to generate a radical pair which subsequently recombines to produce the mixture of oxazolinones.A series of related oxazoles was prepared in which the heterocyclic ring and the ? bond are connected by an alkoxy side chain.All attempts to induce an intramolecular Diels-Alder reaction failed.The only product that could be obtained corresponds to that derived from an intramolecular ene reaction.The excited-state behavior of several 2- and 5-allyloxy-substituted oxazoles was also studied.The rationale for the difference in thermal and photochemical behavior is discussed.