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A novel way to chiral 2-oxazolidinones: selenium-catalyzed cyclocarbonylation of 2-aminoethanols

Selenium-catalyzed cyclocarbonylation of 2-aminoethanols with CO under atmospheric pressure at 30 C afforded 2-oxazolidinones in excellent yields without any other co-catalyst. The method was then applied to the syntheses of chiral 2-oxazolidinones and no racemization was detected.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H740NO – PubChem

 

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Pyrazole-Based Acid Ceramidase Inhibitors: Design, Synthesis, and Structure-Activity Relationships

Acid ceramidase (AC) is a lysosomal cysteine amidase responsible for the cleavage of ceramide into sphingosine, which is then phosphorylated to sphingosine 1-phosphate. AC regulates the intracellular levels of ceramide and sphingosine, and AC inhibition may be useful in the treatment of disorders, such as cancer, in which ceramide-mediated signaling may be dysfunctional. Despite their potential experimental and therapeutic value, the number of available small-molecule inhibitors of AC activity remains limited. In the present study is described the discovery of a class of potent pyrazole carboxamide-based AC inhibitors, which were identified using the atomic property field (APF) approach and developed through systematic SAR investigations and in vitro pharmacological characterization. The best compound of this series inhibits AC with nanomolar potency and causes ceramide accumulation and sphingosine depletion in intact G361 proliferative melanoma cells. By expanding the current armamentarium of AC inhibitors, these results should facilitate future efforts to unravel the biology of AC and the therapeutic potential of its inhibition.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H491NO – PubChem

 

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Preparation of multisubstituted enamides via rhodium-catalyzed carbozincation and hydrozincation of ynamides

(Chemical Equation Presented) Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described.Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.

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Oxazolidine – Wikipedia,
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Enantio- and Diastereo-Selective Synthesis of (+)-Grandisol

(+)-Grandisol, an insect pheromone having cyclobutane skeleton, is synthesized enantio- and diastereoselectively.The key steps in the synthesis are the asymmetric <2+2> cycloaddition reaction catalyzed by a chiral titanium reagent and the diastereoselective conjugate addition reaction by the combined use of Me2CuLi and trimethylsilyl trifluoromethanesulfonate.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H857NO – PubChem

 

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Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling

Due to the low intrinsic acidity of amines, palladium-catalyzed C-N cross-coupling has been plagued continuously by the necessity to employ strong, inorganic, or insoluble bases. To surmount the many practical obstacles associated with these reagents, we utilized a commercially available dialkyl triarylmonophosphine-supported palladium catalyst that facilitates a broad range of C-N coupling reactions in the presence of weak, soluble bases. The mild and general reaction conditions show extraordinary tolerance for even highly base-sensitive functional groups. Additionally, insightful heteronuclear NMR studies using 15N-labeled amine complexes provide evidence for the key acidifying effect of the cationic palladium center.

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Oxazolidine – Wikipedia,
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Intramolecular carbolithiation of heterosubstituted alkynes: An experimental and theoretical study

A series of heterosubstitued alkynes was successfully submitted to the intramolecular carbolithiation of their triple bond. We show that the addition is stereoselective because of the control exerted by the terminal substituent X on the geometry of the transition state. A complementary DFT study suggests that the addition is anti when a strong Li-X interaction occurs.

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Oxazolidine – Wikipedia,
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The alkyne amide […] and phosphine hydrogenation reaction (by machine translation)

The invention discloses an efficient preparation of cis neighbouring alkene diamine and cis-beta – amino alkene phosphonate compounds, to terminal alkyne amide and secondary amine or phosphine reagent as the raw material, cesium carbonate as the alkali, at room temperature reaction to obtain the cis neighbouring alkene diamine compounds and cis-beta – amino alkene phosphonate compound. The present invention achieves the alkyne amide molecule for […] and phosphine hydrogenation reaction to the preparation of cis neighbouring alkene diamine and beta – amino alkene phosphonate compound of the method, the method is simple and feasible, mild reaction conditions, wide application prospects. (by machine translation)

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Oxazolidine – Wikipedia,
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Thermolysis Reaction of 2-Acetyl-1-Oxo-Five-, Six-, and Seven-Membered Ring

The rates of gas-phase thermolysis reactions of 2-acetylcyclopentanone 1, 2-acetylcyclohexanone 2, N-acetylcaprolactam 3, 2-acetylbutyrolactone 4, 2-acetyl-2-methylbutyrolactone 5, and 3-acetyl-2-oxazolidinone 6 have been measured over a temperature range of 50 K.They undergo unimolecular first-order elimination reactions for which log A = 11.7, 11.7, 11.2, 11.4, 11.5, and 11.1 s-1 and Ea = 193.4, 189.5, 153.2, 201.0, 206.8, and 176.1 kJ mol-1, respectively.The effect of the ring size together with the effect of a heteroatom in the ring on the rate of thermolysis reactions for compounds 1-6 is the subject of this work.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H282NO – PubChem

 

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Stereoselective Diels-Alder reactions of 3-phosphonopropenoyl derivatives of 1,3-oxazolidin-2-ones

Dienophiles of the general structure (EtO)2P(O)CH{double bond, long}CHCOX have been prepared, where X represents an oxazolidinone chiral auxiliary. Use of the (S)-4-isopropyl-5,5-diphenyl-1,3-oxazolidin-2-one auxiliary gave Diels-Alder adducts with several cyclic and acyclic dienes. The crystal structures of the main cyclohexa-1,3-diene and 2,3-dimethylbutadiene adducts formed during reactions in the presence of dialkylaluminium halides are consistent with a reaction, which is stereoselectively endo with respect to the carbonyl group and occurs on the less hindered face of the dienophile when aluminium is chelated between the two carbonyl groups.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H433NO – PubChem

 

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Vibrational assignments of five-membered heterocyclic compounds. Normal vibrations of oxazolidine-2-one and -2-thione

Infrared spectra of oxazolidine-2-one (Oxo), -2-thione (Oxt) and their N-deuteriated derivatives have been measured over the range 4000 – 20 cm-1.The fundamental frequencies of these molecules have been assigned on the basis of normal coordinate calculations carried out using a Urey-Bradley potential function supplemented with valence type constants for the out-of-plane modes of the planar skeleton.The results of the vibrational analyses are discussed and correlated with the assignments available for the other related five membered heterocyclic molecules.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H487NO – PubChem