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Base-promoted aminoethylation of thiols with 2-oxazolidinones: A simple synthesis of 2-aminoethyl sulfides

A simple synthesis of 2-aminoethyl sulfides using a base-promoted reaction of 2-oxazolidinones with thiols is described. An application of this method to the synthesis of chiral 2-aminoethyl sulfides and sulfur-containing heterocyclic compounds is also presented.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H640NO – PubChem

 

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Rhodium(II)-catalyzed c-h functionalization of electron-deficient methyl groups

Enantioselective C-H functionalization of relatively electron-deficient methyl sites was achieved with the combination of 2,2,2-trichloroethyl aryldiazoacetates and tetrakis(triarylcyclopropanecarboxylate) dirhodium catalysts. The substrate scope of the transformation was relatively broad, and C-H functionalization products were furnished with excellent levels of enantioselectivity. As a strategic reaction, crotonate derivatives give 1,6-dicarbonyl compounds, which are useful for further diversification.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H531NO – PubChem

 

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Expanding the scope of the acyl-type radical addition reactions promoted by SmI2

N-Acyl oxazolidinones of simple carboxylic acids and amino acids were observed to undergo successful SmI2-promoted couplings with substituted acrylamides and acrylates, affording a variety of functionalized gamma-ketoamides and -esters with yields attaining 85%. As many of these reductive couplings were previously found to be ineffective employing the corresponding 4-pyridylthio esters, the applicability of this methodology has been substantially improved. The methodology has been adapted to prepare structures related to two potent aspartate protease inhibitors, the renin inhibitor aliskiren, and the gamma-secretase inhibitor L-685,458. Finally, a convenient two-step procedure for the preparation of N-acyl oxazolidinones of N-protected amino acids, which provides consistently good yields of the corresponding imide, has been devised.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H680NO – PubChem

 

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Biarylpyrazolyl oxadiazole as potent, selective, orally bioavailable cannabinoid-1 receptor antagonists for the treatment of obesity

Since the CB1 cannabinoid receptor antagonist 1 (SR141716, rimonabant) was previously reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. In the present study, biarylpyrazole analogues based on a pyrazole core coupled with 1,3,4-oxadiazole were synthesized and tested for CB1 receptor binding affinity. Thorough SAR studies to optimize pyrazole substituents as well as 1,3,4-oxadiazole ring led to several novel CB1 antagonists with IC50 ? 1 nM for the CB1 receptor binding. Among these analogues, we identified 2-(4-((1H-1,2,4-triazol- 1-yl)methyl)-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl) -5-(1-(trifluoromethyl)cyclopropyl)-1,3,4-oxadiazole 43c as a promising precandidate for the development as an antiobesity agent.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1031NO – PubChem

 

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ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS

Described herein are compounds that are antagonists of PGD2 receptors. Also described are pharmaceutical compositions and medicaments that include the antagonists of PGD2 receptors described herein, as well as methods of using such antagonists of PGD2 receptors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other PGD2-dependent or PGD2-mediated conditions or diseases.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H127NO – PubChem

 

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Palladium(II)-Catalyzed Amidation of Alkenes

PdCl2(MeCN)2 catalyzes amidation of electron-deficient alkenes leading to enamides, where cyclic carbamates are more reactive than cyclic amides as nucleophiles.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H618NO – PubChem

 

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Thermal Degradation of Morpholine in CO2 Post-combustion Capture

Aqueous monoethanolamine (MEA) has been used as benchmark solvent in CO2 capture systems due to its fast absorption kinetics, high cyclic capacity and low cost. However, operational challenges make MEA potentially less attractive, and therefore; there has been a high demand to develop new solvent systems, such as morpholine (MOR). Accordingly, in this work, thermal degradation studies using MEA or MOR have been conducted under stripper conditions in a post-combustion CO2 capture system to identify operational challenges associated with amines degradation. The comparison of MEA and MOR degradation shows that MOR is more thermally stable when compared with MEA in the presence of CO2 at stripper operating conditions studied here. Initial test results identified 1-(2-Hydroxyethyl)-2-imidazolidinone as thermal degradation of MEA, but they were not observed for MOR. Published by Elsevier Ltd.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H867NO – PubChem

 

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Regio- and stereoselective synthesis of 1,4-dihydropyridines by way of an intramolecular interaction of a thiocarbonyl or carbonyl with a pyridinium nucleus

Chiral 1,4-dihydropyridines were prepared by the regio- and stereoselective addition of ketene silyl acetals and organometallic reagents to pyridinium salts. In the addition reaction, an intramolecular interaction between the thiocarbonyl or carbonyl with the pyridinium nucleus plays an important role in bringing about the selectivities. The absolute configuration of the newly produced stereogenic center of the 1,4-dihydropyridines was determined by X-ray analysis and CD Cotton effects after conversion into the appropriate derivatives. The working model for the stereoselectivity was proposed based on the ab initio calculations at the RHF/3-21G* level.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1161NO – PubChem

 

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N-Acyliminium ion chemistry and palladium catalysis: A useful combination to obtain bicyclic heterocycles

By using N-acyliminium ion chemistry, several omega-propadienyllactams and a propadienyloxazolidine were prepared from N-acyliminium ion precursors and propargylsilanes. Treatment of these allene containing lactams and oxazolidinone with allyl halides or an allyl carbonate using Pd(II)-salts as the catalyst gave rise to a coupling-cyclization reaction, yielding bicyclic systems in which the allyl moiety is incorporated. With this methodology several substituted pyrrolizinones, an oxazolone and indolizinone were prepared.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H684NO – PubChem

 

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RORC2 INHIBITORS AND METHODS OF USE THEREOF

The present invention provides compounds, pharmaceutical compositions, methods of inhibiting RORgamma activity and/or reducing the amount of IL-17 in a subject, and methods of treating various medical disorders using such compounds and pharmaceutical compositions.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H219NO – PubChem