703-56-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenyl-2-oxazolidinone is used as a therapeutic agent for the treatment of type 2 diabetes. Its structure allows it to potentially modulate key biological targets involved in glucose metabolism and insulin sensitivity, offering a new avenue for managing this prevalent metabolic disorder.
Given the provided information, there is only one application mentioned for 3-Phenyl-2-oxazolidinone, which is its use in the pharmaceutical industry for treating type 2 diabetes. If additional applications or industries were to be identified in the future, they could be listed separately following the format provided.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2977, 1986 DOI: 10.1021/jo00365a024

InChI:InChI=1/C9H9NO2/c11-9-10(6-7-12-9)8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 75-21-8 oxirane 
• 123-91-1 1,4-dioxane 
• 71-91-0 tetraethylammonium bromide 
• 103-71-9 phenyl isocyanate 
• 110-86-1 pyridine 
• 3747-48-6 1-chloro-2-phenylcarbamoyloxy-ethane 
• 705-65-7 [1,3]dithiolan-2-ylidenephenylamine 
• 497-25-6 dimethylenecyclourethane 
• 108-86-1 bromobenzene 
• 62-53-3 aniline 
• 696-18-4 1-phenylaziridine 
• 124-38-9 carbon dioxide 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 122-98-5 2-Anilinoethanol 

Downstream Products

• 21089-36-1 3-phenylthiazolidin-2-one 
• 5888-88-0 3-phenyl-1,3-oxazolidin-2-thione 
• 1313524-78-5 C₁₅H₁₁F₂NO₂ 
• 1075-76-9 N-cyanoethylaniline 
• 199387-45-6 4-phenyl-3-((E)-3-phenylacryloyl)oxazolidin-2-one 
• 5319-52-8 N-[2-(piperidin-1-yl)ethyl]aniline 
• 36716-44-6 N-[2-(pyrrolidin-1-yl)ethyl]aniline 
• 2346-26-1 2,4-oxazolidinedione 
• 935-06-8 N-(2-chloroethyl)aniline 
• 1739-00-0 (N-phenyl)phenylethylamine 
• 15719-64-9 methylammonium carbonate 
• 92249-42-8 N-Phenyl-2-phenylsulfanylethylamine 
• 143745-61-3 N-(3-methylphenyl)-N'-phenyl-1,2-ethanediamine 

Relevant academic research and scientific papers

The Synthesis of 3-Aryl-2-oxazolidinones from CO2, Ethylene Oxide, and Anilines Under Mild Conditions Using PVA-DFNT/Ni

Abstract: A novel nanocatalyst design using nanomaterials through active-zone crystallisation was proposed. The hydrothermal crystallisation of amorphous dendritic fibrous nano-titanium dioxide with Ni (DFNT/Ni) sites was determined to be the main step in producing extremely active dendritic DFNT/Ni zones, which in turn dramatically enhanced their catalytic activities. DFNT/Ni was then combined with polyvinyl alcohol (PVA) by using a traditional individual-nozzle electrospinning method, and the resulting material was named PVA-DFNT/Ni. This method was utilised to produce 3-aryl-2-oxazolidinones from ethylene oxide, CO2, and anilines. The prepared catalytic apparatus was eco-friendly and had the advantages of high catalytic activity, ability to improve the reaction mixture, and reusability without a considerable decrease in efficiency. It is extracted in the straight and adoptive chemical fixation of flue-gas CO2 obtained from industrial emissions, thereby achieving high degrees of CO2 absorption and conversion. Graphic Abstract: [Figure not available: see fulltext.].

Synergetic activation of CO2by the DBU-organocatalyst and amine substrates towards stable carbamate salts for synthesis of oxazolidinones

The development of an efficient methodology to transform CO2 into valuable chemicals has attracted increasing attention concerning the challenging issues of CO2-utilization. Herein, an efficient approach for the preparation of oxazolidinones from CO2, primary (aliphatic/aromatic) amines and 1,2-dichloroethane (or its derivatives) catalyzed by DBU organo-superbase was achieved with yields of 47-97% under mild conditions (80-100 °C, 12 h, 1.0 MPa CO2). Control experiments demonstrated that the formation of an ion-pair carbamate salt intermediate IS-B derived from the reaction of CO2, DBU (catalyst) and an amine (substrate) was the key step for this three-component reaction. The available DBU-amine-CO2 adduct intermediate (like IS-B-2) with fair stability will evolve into the thermodynamically stable product oxazolidinones upon attack of 1,2-dichloroethane (or its derivatives), along with the regeneration of the DBU catalyst. Alternatively, the decomposition of the DBU-aryl amine-CO2 adduct (like IS-B-1) with relatively poor stability also could result in the competitive substitution reaction of 1,2-dichloroethane (or its derivatives) with the aryl amine. This work provides insights into synergetic CO2-activation by the DBU-catalyst and a nucleophilic amine-substrate via the formation of robust carbamate salt intermediates responsible for the final production of oxazolidinones. This journal is

Nickel-catalyzed N-arylation of amines with arylboronic acids under open air

In this study, a well-defined, novel NHC-Ni complex was developed and used to catalyze the N-arylation of alkyl- and arylamines with arylboronic acids in a rare version of Chan-Lam coupling. Although the same coupling using copper catalysts has been widely studied, the nickel-catalyzed version is rare and normally requires 10–20 mol% catalyst loading. This novel NHC-Ni complex in combination with 4,4′-dimethyl-2,2′-bipyridine, however, proved to be an effective catalyst that lowered the required catalyst loading to only 2.0 mol%.

Method for synthesizing N - aryl oxazolidine -2 - ketone compound by ionic liquid catalysis

The invention discloses a method for catalytic synthesis of a N-aryloxazolane-2-one compound or a chiral N-aryloxazolane-2-one compound from an ionic liquid. The process of the preparation method is as follows: a catalytic amount of ionic liquid is added

Method for synthesizing cyclic amide from carbon dioxide

The invention discloses a method for synthesizing cyclic amide from carbon dioxide. An aromatic amino compound, 1 atm carbon dioxide and a halogenated compound undergo a one-step reaction under the synergistic action of N-doped TiO2 and an inorganic salt catalyst to generate the cyclic amide. Studies find that visible light has an obvious promoting effect on the conversion process. The chemical selectivity of the cyclic amide compound can be regulated by regulating conditions such as reaction temperature, time and illumination. The catalyst can be recycled for five times after being separatedand dried, and the activity and the chemical selectivity can be well maintained. The synthesis method has the advantages of simple synthetic route, novelty, simple process, high yield and high purityof the product, cheap and easily available catalyst, no influences on the environment, and suitableness for industrial production.

Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.

Spirulina (Arthrospira) platensis Supported Ionic Liquid as a Catalyst for the Synthesis of 3-Aryl-2-oxazolidinones from Carbon Dioxide, Epoxide, Anilines

Abstract: This study investigates the potential application of the (Ammonio)butane-1-sulfonate modified Spirulina (Arthrospira) platensis biomasses in the synthesis of 3-aryl-2-oxazolidinones from CO2, ethylene oxide, and anilines. High catalytic activity and ease of recovery from the reaction mixture using filtration and several reuse times without significant losses in performance are additional eco-friendly attributes of this catalytic system. The effects of the structure of ionic liquid on the catalytic performance were investigated and the various reaction conditions were optimized. This observation was exploited in the direct and selective chemical fixation of CO2, affording high degrees of CO2 capture and conversion. Graphical Abstract: [Figure not available: see fulltext.].

Synthesis of N-aryl-2-oxazolidinones from cyclic carbonates and aromatic amines catalyzed by bio-catalyst

A convenient and effective method of synthesizing 3-aryl-2-oxazolidinones from cyclic carbonates and aryl amines catalyzed by bio-catalyst adenine in the presence of Et3N under solvent-free conditions is described. The protocol is suitable for the wide scope of substrates, e.g. cyclic carbonates with or without substitutes, and aryl amines with either electron-withdrawing or electron-donating group. The products were obtained in good to excellent yields under the optimal conditions, even in steric hindered cases. The effect of reaction time, temperature, loading of catalyst, and amount of starting materials in the reaction were investigated, and the reaction mechanism is discussed.

Ruthenium-Pincer-Catalyzed Hydrogenation of Lactams to Amino Alcohols

By using the commercially available ruthenium pincer complex (Ru-MACHO-BH) as a catalyst, the challenging direct hydrogenation of lactams and analogues has been successfully accomplished to deliver corresponding value-added amino alcohols in good-to-excellent yields under mild reaction conditions. Remarkably, in addition to N-protected lactams, unprotected ones could also be readily reduced in the presence of a catalytic amount of weak base or even under neutral reaction conditions, which further highlights the broad substrate scope and the protocol efficiency.

Synthesis of Oxazolidinones and Derivatives through Three-Component Fixation of Carbon Dioxide

An effective three-component fixation of atmospheric CO2 with readily available 1,2-dichloroethane and aromatic amine toward oxazolidinones catalyzed by in situ NHC was developed. The reaction occurred in good to excellent yields with good gene