7426-72-4

Upstream product

• 96-09-3 styrene oxide 
• 103-71-9 phenyl isocyanate 
• 103-72-0 phenyl isothiocyanate 
• 2952-05-8 1,2-diphenylaziridine 
• 124-38-9 carbon dioxide 
• 62-53-3 aniline 
• 100-42-5 styrene 
• 4427-92-3 4-Phenyl-1,3-dioxolan-2-one 
• 99342-73-1 1-phenyl-2-phenylaminoethanol 
• 101-99-5 N-carboethoxyaniline 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 94041-13-1 3,5-Diphenyl-oxazolidine-2-thione 

Relevant academic research and scientific papers

Microwave-Assisted Electrostatically Enhanced Phenol-Catalyzed Synthesis of Oxazolidinones

An electrostatically enhanced phenol is utilized as a straightforward, sustainable, and potent one-component organocatalyst for the atom-economic transformation of epoxides to oxazolidinones under microwave irradiation. Integrating a positively charged center into phenols over a modular one-step preparation gives rise to a bifunctional system with improved acidity and activity, competent in rapid assembly of epoxides and isocyanates under microwave irradiation in a short reaction time (20-60 min). A careful assessment of the efficacy of various positively charged phenols and anilines and the impact of several factors, such as catalyst loading, temperature, and the kind of nucleophile, on catalytic reactivity were examined. Under neat conditions, this one-component catalytic platform was exploited to prepare more than 40 examples of oxazolidinones from a variety of aryl- and alkyl-substituted epoxides and isocyanates within minutes, where up to 96% yield and high degree of selectivity were attained. DFT calculations to achieve reaction barriers for different catalytic routes were conducted to provide mechanistic understanding and corroborated the experimental findings in which concurrent epoxide ring-opening and isocyanate incorporation were proposed.

The catalytic system ‘Rhodamine B/additive’ for the chemical fixation of CO2

The catalytic system ‘Rhodamine B/additive’ was introduced to promote the CO2 reactions. We synthesized various cyclic carbonates in good to excellent yields under the catalysis of rhodamine B and TBAB. A variety of 2-oxazolidinone derivatives were obtained in the presence of rhodamine B and DBU.

Reaction Mechanism of CO2and Styrene Oxide Catalyzed by Ionic Liquids: A Combined DFT Calculation and Experimental Study

Bioactive compound 3-aryl-2-oxazolidinone could be synthesized by a green method mixing carbon dioxide, aniline, and ethylene oxide. Our group previously proposed a parallel mechanism for this conversion catalyzed by ionic liquids. Recently, a new study o

Triethylamine Hydroiodide as a Bifunctional Catalyst for the Solvent-Free Synthesis of 2-Oxazolidinones

Among the wide variety of heterocycles, 2-oxazolidinones are recognized as some of the most important heterocyclic compounds in medicinal chemistry. Therefore, the development of a practical method for their synthesis would be an important development. He

Squaramide–Quaternary Ammonium Salt as an Effective Binary Organocatalytic System for Oxazolidinone Synthesis from Isocyanates and Epoxides

Squaramide–quaternary ammonium salt is illustrated as a simple, tunable, and competent metal-free binary catalytic platform for the atom-economic conversion of epoxides and isocyanates into oxazolidinones. Although, various metal catalysts have been employed for the title reaction, application of organocatalysis is scarce. At first, a rational survey of catalytic activity of several air-stable and architecturally distinct squaramides was undertaken. Thereafter, the impact on catalytic capability of different parameters, such as temperature, catalyst loading, and nature of nucleophiles, was examined. This binary organocatalytic system for the oxazolidinone synthesis, composed of a squaramide entity along with a suitable halide anion, was applied to the challenging conversion of a plethora of alkyl- and aryl-substituted epoxides– including disubstituted and enantioenriched ones– and isocyanates into the corresponding oxazolidinones in high-to-excellent yields. The time-dependent formation of oxazolidinone from epoxide and isocyanate was monitored by FTIR-ATR and 1H NMR spectroscopy and the scalability of this process was also described. In light of 1H NMR experiment, a hydrogen-bonding/anion-binding mechanism was proposed wherein the nucleophilic ring-opening operation, and oxo- and carbamate-anions stabilization occur cooperatively towards isocyanate fixation.

Green synthesis of Dy2Ce2O7 Nanoparticles Immobilized on Fibrous Nano-silica for Synthesis of 3-Aryl-2-oxazolidinones from Alkenes, Amines, and Carbon Dioxide

Abstract: In the present research, a new dendritic fibrous nanosilica (DFNS) based nanocatalyst (DFNS/Dy2Ce2O7) that has high surface zone as well as easy availability of active zones has been properly expanded using an easy approach. DFNS that possess high surface zone is functionalized by amino groups working as the anchors such that the nanoparticles of Dy2Ce2O7 are fine-dispersed onto the DFNS microspheres fibres, without any aggregation. The nanoparticles of Dy2Ce2O7 are produced by a green approach in the attendance of gum of ferula assa-foetida of Dy(NO3)3 and (NH4)2Ce(NO3)6 as ceric and dysprosium sources. The structural evaluation of the samples proved the synthesis of Dy2Ce2O7 NPs. Moreover, a straight way for the production of 3-aryl-2-oxazolidinones by carbon dioxide, olefins, and anilines was obtained utilizing nano catalyst of DFNS/Dy2Ce2O7 in the lack of solvent. The reaction works properly at moderate states. This method that is cheap and simple may be used to different olefins that has proper to excellent 3-aryl-2-oxazolidinones productions. The catalyst may be simply recycled for ten times without considerable losing the activity of its catalytic. Graphic Abstract: [Figure not available: see fulltext.]

Bifunctional organocatalysts for the conversion of CO2, epoxides and aryl amines to 3-aryl-2-oxazolidinones

A route to synthesize 3-aryl-2-oxazolidinones is developed, which is achieved through a three component reaction between CO2, aryl amines, and epoxides with a binary organocatalytic system composed of organocatalysts and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The method allows wide scopes of epoxide and aryl amine substrates with various functional groups under mild reaction conditions. The control experiments indicate that a cyclic carbonate is formed via cycloaddition of epoxides with CO2, which further reacts with the β-amino alcohol originating from epoxides and aryl amines, resulting in the formation of 3-aryl-2-oxazolidinones finally.

A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare-Earth Metal Amides

Three-component reaction of epoxides, amines, and dimethyl carbonate catalyzed by rare-earth metal amides has been developed to synthesize oxazolidinones. 47 examples of 3,5-disubstituted oxazolidinones were prepared in 13–97 % yields. This is a simple and most practical method which employs easily available substrates and catalysts, and is applicable to a wide range of aromatic and aliphatic amines, as well as mono-substituted epoxides. Scope of disubstituted epoxides is rather limited, which requires further study. Preliminary mechanistic study reveals two possible reaction pathways through intermediates of β-amino alcohols or amides.

Influence of the catalyst structure in the cycloaddition of isocyanates to oxiranes promoted by tetraarylstibonium cations

In the context of our work on electron deficient group 15 cations as Lewis acid catalysts, we have synthesized the triflate salts of a series of tetraarylstibonium cations of general formula [ArSbPh3]+ with Ar = Mes (4+), o-(dimethylamino)phenyl (5+), and o-((dimethylamino)methyl)phenyl (6+). These new cationic antimony derivatives, along with the known [Ph4Sb]+ (1+), 1-naphthyltriphenylstibonium (2+), and [(Ant)SbPh3]+ (3+), have been evaluated as catalysts for the cycloaddition of oxiranes and isocyanates under mild conditions. While all stibonium cations favor the 3,4-oxazolidinone products, the reactivities of 5+ and 6+ are hindered by the ancillary amino donor which quenches the Lewis acidity of the antimony center. A comparison of the other stibonium cations shows that 4+ is the most selective catalyst.

Potassium phosphate-catalyzed one-pot synthesis of 3-aryl-2-oxazolidinones from epoxides, amines, and atmospheric carbon dioxide

Potassium phosphate was found to be a highly active catalyst in the three-component cycloaddition of amines, epoxides, and carbon dioxide in DMF at ambient temperature to form 3-aryl-2-oxazolidinones. Atmospheric CO2 and a broad range of amines were employed in this transformation. Aryl isocyanate and 1,2-aminoalcohol were generated in situ as key intermediates. This one-pot reaction is applicable to a variety of terminal epoxides and amines. The key advantages are high yields, simple work-up, inexpensive catalysts, and a practical ten gram-scale synthesis.