5198-45-8

Upstream product

• 96-49-1 [1,3]-dioxolan-2-one 
• 108-44-1 1-amino-3-methylbenzene 
• 497-25-6 dimethylenecyclourethane 
• 591-17-3 meta-bromotoluene 
• 625-95-6 3-Iodotoluene 
• 124-38-9 carbon dioxide 
• 107-06-2 1,2-dichloro-ethane 
• 627-11-2 2-Chloroethyl chloroformate 
• 5602-93-7 ethyl (2-hydroxyethyl)carbamate 
• 18437-67-7 1,1-dimethylethyl (3-methylphenyl)carbamate 
• 75-44-5 phosgene 
• 102-41-0 1-(2-hydroxyethyl)amino-3-methylbenzene 
• 32508-30-8 m-tolyl-carbamic acid-(2-chloro-ethyl ester) 

Downstream Products

• 1313524-86-5 C₁₆H₁₃F₂NO₂ 
• 1313524-85-4 C₁₆H₁₃Cl₂NO₂ 
• 102-41-0 1-(2-hydroxyethyl)amino-3-methylbenzene 

Relevant academic research and scientific papers

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

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.

Efficient and Mild Ullmann-Type N-Arylation of Amides, Carbamates, and Azoles in Water

A simple, sustainable, efficient, mild, and low-cost protocol was developed for d-glucose-assisted Cu-catalyzed Ullmann reactions in water for amides, carbamates, and nitrogen-containing heterocycles. The reaction was compatible with diverse aryl/heteroaryl iodides, giving highly substituted pyridine, indole, or indazole rings. This method offers an attractive alternative to existing protocols, because the reaction proceeds in aqueous media, occurs at or near ambient temperature, and provides the N-arylated products in good to high yields.

Bis-aryl urea derivatives as potent and selective LIM kinase (Limk) inhibitors

The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 1 μM), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 μM inhibited only Limk1 and STK16 with ≥80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

Copper-Catalyzed One-Pot Synthesis of N -Aryl Oxazolidinones from Amino Alcohol Carbamates

An efficient sequential intramolecular cyclization of amino alcohol carbamates followed by Cu-catalyzed cross-coupling with aryl iodides under mild conditions has been developed. The reaction occurred in good yields and tolerated aryl iodides containing functionalities such as nitriles, ketones, ethers, and halogens. Heteroaryl iodides and substituted amino alcohol carbamates were also well tolerated.

CuI/N,N-dimethylglycine-catalyzed synthesis of N-aryloxazolidinones from aryl bromides

CuI/N,N-dimethylglycine catalyzed coupling of aryl bromides with substituted oxazolidinones took place at 120 °C in DMF, affording the corresponding N-arylation products with good to excellent yields. A number of functional groups, such as ketone, nitrile, nitro, methoxy, and hydroxyl were tolerated under these conditions, thereby allowing diversity synthesis of N-aryloxazolidinones.

Novel syntheses of N-aryloxazolidin-2-ones via tandem reactions of vinyl sulfonium salts

An unprecedented and efficient domino reaction of diphenyl vinyl sulfonium salt with carbamates leading to the syntheses of N-aryloxazolidin-2-ones has been developed. The scope of this transformation has been studied and a plausible mechanism has been pr

Short and practical synthesis of N′,N′-disubstituted N-aryl-1,2-ethylene-diamines by a decarboxylative ring-opening reaction under nucleophilic conditions

A straightforward and practical synthesis of N′,N′- disubstituted N-aryl-1,2-ethylenediamines, starting from anilines, via N-aryloxazolidin-2-ones is described. A decarboxylative ring-opening reaction of N-aryloxazolidin-2-ones, using aliphatic secondary

Highly efficient CuI-catalyzed coupling of aryl bromides with oxazolidinones using Buchwald's protocol: a short route to linezolid and toloxatone.

[reaction: see text] Coupling of a variety of substituted aryl bromides with oxazolidinones has been achieved using the Buchwald protocol for the amidation of aryl halides. This procedure is exemplified by the synthesis of two medicinally important molecules, linezolid and toloxatone.

Synthesis and Spectral Behavior of 5-Methyl-3-phenyl-1,3-oxazolidin-2-ones Using NMR

Heterocyclic compounds of four 5-methyl-3-phenyl-1,3-oxazolidin-2-ones have been synthesized by the reaction of N-2-hydroxyethyl- or N-2-hydroxypropylanilines with phosgene in the presence of pyridine.From the spectral behavior, the title compounds are found to exist in the trans and cis forms.