5198-46-9

Usage

InChI:InChI=1/C10H11NO2/c1-8-2-4-9(5-3-8)11-6-7-13-10(11)12/h2-5H,6-7H2,1H3

Upstream product

• 96-49-1 [1,3]-dioxolan-2-one 
• 106-49-0 p-toluidine 
• 497-25-6 dimethylenecyclourethane 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 14618-59-8 N-(tert-butoxycarbonyl)-4-methylaniline 
• 75-21-8 oxirane 
• 124-38-9 carbon dioxide 
• 107-06-2 1,2-dichloro-ethane 
• 106-93-4 ethylene dibromide 
• 627-11-2 2-Chloroethyl chloroformate 
• 5602-93-7 ethyl (2-hydroxyethyl)carbamate 
• 5720-05-8 4-methylphenylboronic acid 
• 74552-28-6 N-(p-Tolyl)carbamidsaeure-β-chlorethylester 

Downstream Products

• 28690-22-4 3-(p-tolyl)thiazolidin-2-one 
• 71472-58-7 3,4-dihydro-7-methyl-2H-1,4-benzoxazine 
• 2933-74-6 2-[(4-methylphenyl)amino]-ethanol 
• 1313524-80-9 C₁₆H₁₃Cl₂NO₂ 
• 1313524-81-0 C₁₆H₁₃F₂NO₂ 
• 1313524-82-1 C₁₆H₁₃ClFNO₂ 
• 1077-24-3 3-(p-tolylamino)propionitrile 

Relevant academic research and scientific papers

Room Temperature Cu-Catalyzed N-Arylation of Oxazolidinones and Amides with (Hetero)Aryl Iodides

N,N′-Bis(pyridin-2-ylmethyl)oxalamide (BPMO) was found to be an apposite promoter for the Cu-catalyzed N-arylation of oxazolidinones and primary and secondary amides with (hetero)aryl iodides at room temperature. Excellent chemoselectivity reached between

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.].

METHODS FOR PREPARING BENZOXAZINES

A method is provided for preparing a compound / the method comprising carrying out the following reaction: Formula (i); Formula (ii) where: R10 is hydrogen or a hydroxy protecting group; PG is an amine protecting group; and q is 1 where PG is a

Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines

The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.

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

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.

A straightforward one-pot synthesis of bioactive: N -aryl oxazolidin-2-ones via a highly efficient Fe3O4@SiO2-supported acetate-based butylimidazolium ionic liquid nanocatalyst under metal- and solvent-free conditions

In the present study, we report the fabrication and characterization of novel acetate-based butylimidazolium ionic liquid immobilized silica-coated magnetic nanoparticles (IL-OAc@FSMNP). The synthesized nanocomposite proves its supremacy as an environmentally benign catalyst in the reaction of aniline and its derivatives with ethylene carbonate to form bioactive N-aryl oxazolidin-2-ones under metal-, ligand-, and solvent-free conditions. The catalyst offers excellent assemblies of hydrogen-bond donors and acceptors, which activate the substrates, thereby delivering good-to-excellent product yields with a conversion and selectivity of more than 99%. Additionally, mild reaction conditions, wide substrate scope, effortless catalytic recovery and recyclability of the catalyst up to eight consecutive cycles offer the potential for scale-up in various pharmaceutical applications.

DBU and DBU-Derived Ionic Liquid Synergistic Catalysts for the Conversion of Carbon Dioxide/Carbon Disulfide to 3-Aryl-2-oxazolidinones/[1,3]Dithiolan-2-ylidenephenyl- Amine

An intermolecular synergistic catalytic combination of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and a DBU-derived bromide ionic liquid has been developed for the conversion of CO2, epoxides, and amines under metal- And solvent-free conditions. Various 3-aryl-2-oxazolidinones are produced in moderate to excellent yields within a short reaction time. NMR spectroscopy and DFT calculations demonstrate that DBU as a hydrogen bond acceptor and the ionic liquid as a hydrogen bond donor activate the substrates cooperatively by inducing hydrogen bonds to promote the reaction effectively. Based on these results, a possible reaction mechanism on the synergistic catalysis of DBU and the ionic liquid is proposed. In addition, the reaction of CS2, ethylene oxide, and aniline catalyzed by the combination of DBU and the DBU-derived ionic liquid also proceeds smoothly, which opens a hitherto unreported route to [1,3]dithiolan-2-ylidenephenylamine in a straightforward way.

A One-Pot Synthesis of N-Aryl-2-Oxazolidinones and Cyclic Urethanes by the Lewis Base Catalyzed Fixation of Carbon Dioxide into Anilines and Bromoalkanes

The multicomponent assembly of pharmaceutically relevant N-aryl-oxazolidinones through the direct insertion of carbon dioxide into readily available anilines and dibromoalkanes is described. The addition of catalytic amounts of an organosuperbase such as Barton's base enables this transformation to proceed with high yields and exquisite substrate functional-group tolerance under ambient CO2pressure and mild temperature. This report also provides the first proof-of-principle for the single-operation synthesis of elusive seven-membered ring cyclic urethanes.