Some scientific research about Oxazolidin-2-one

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Paroxetine is a trans-3,4-disubstituted piperidine compound that exhibits important medicinal properties. Over the past few decades, various strategies have been revealed in application to its synthesis. This review will highlight some of the synthetic approaches developed for paroxetine in past ten years. The goal of this review is to showcase recent strategies used to synthesize paroxetine with the anticipation that other novel syntheses will be revealed in the near future.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H657NO – PubChem

 

Properties and Exciting Facts About 144542-43-8

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Chemistry is traditionally divided into organic and inorganic chemistry. COA of Formula: C5H7NO4, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent,Which mentioned a new discovery about 144542-43-8

The iodine-atom-transfer 8-endo cyclization of alpha-carbamoyl radicals was investigated experimentally and theoretically. With the aid of Mg(CIO 4)2 and a bis(oxazoline) ligand, N- ethoxycarbonylsubstituted N-(pent-4-enyl)-2-iodoalkanamides underwent 8-endo cyclization leading to the formation of only the corresponding 3,5-trans-substituted azocan-2-ones in excellent yields. Similarly, the BF 3·OEt2/H2O-promoted reactions of N-ethoxycarbonyl-N-(2-allylaryl)-2-iodoalkanamides afforded exclusively the benzazocanone products with a 3,5-cis configuration in high yields. The bidentate chelation of substrate radicals not only significantly improved the efficiency of cyclization but also resulted in the change of stereochemistry of azocanone products from 3,8-iransto 3,8-cis. Theoretical calculations at the UB3LYP/6-31G* level revealed that the cyclization of N-carbonyl- substituted alpha-carbamoyl radicals occurs via the E-conformational transition states without the presence of a Lewis acid. On the other hand, the cyclization proceeds via the Z-conformational transition states when the substrates form the bidentate chelation with a Lewis acid. In both cases, the 8-endo cyclization is always fundamentally preferred over the corresponding 7-exo cyclization. The complexed radicals having the more rigid conformations also allow the better stereochemical control in the iodine-atom-abstraction step. To further understand the reactivity of a-carbamoyl radicals, the competition between the 8-endo and 5-exo cyclization was also studied. The results demonstrated that the 8-endo cyclization is of comparable rate to the corresponding 5-exo cyclization for a-carbamoyl radicals with fixed Z-conformational transition states. As a comparison, the 8-endo mode is fundamentally preferred over the 5-exo mode in the cyclization of NH-amide substrates because the latter requires the Z-conformational transition states, whereas the former proceeds via the more stable E-conformational transition states.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1470NO – PubChem

 

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Five suitably protected enantiomerically pure beta2-amino acids, homologues of proteinogenic alpha-amino acids, were synthesized from the common chiral precursor, tert-butyl succinyloxazolidinone. Georg Thieme Verlag Stuttgart.

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A new strategy which uses very cheap FeCl3 as an effective catalyst in the presence of Me3SiCl has been developed for the conjugate addition of enones and chalcone with unactivated weakly nucleophilic carbamates.

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Oxazolidine – Wikipedia,
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The Absolute Best Science Experiment for (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one

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The heterocyclic compound specified in the title (and readily prepared from commercial precursors) has a sterically protected C=O group, so that direct lithiation by BuLi at the exocyclic CH2 group is possible (3 ? Li-3). The lithiated N,S-acetal derivative (Li-3) adds diastereoselectively to aldehydes (Table 2), unsymmetrical ketones (Table 3), chalcone (1,4-addition, Scheme 2), and N-phosphinoyl-and N-sulfonylimines (Table 4). Protection of the newly formed OH groups (Scheme 3) and/or MeS/OH displacement by Hg(O2CCF3)2 in aqueous THF/acetonitrile converts the N,S-acetals into hemiaminals (? 20) which, in turn, are readily cleaved to aldehydes, with recovery of the chiral auxiliary (1, Scheme 4). The aldehydes (especially those lacking alpha-carbonyl hydrogens) may be isolated, or they are trapped in situ by reduction to (selectively protected) diols or amino alcohols, by addition of Grignard or Li reagents, which provides diols with two stereogenic centers, by oxidation to give 2-hydroxy esters, or by olefination to provide 4-hydroxy-2-alkenoates (Scheme 5). The scope and limitations of the new, overall enantioselective transformation are determined, and the readily recovered chiral auxiliary used is compared with oxazolidinones of other substitution patterns (Scheme 7). The configuration of a number of products has been assigned by single-crystal X-ray diffraction (cf. Figure 5). These structures and similarities of NMR data led to configurational assignment of the other products (see formulas in the schemes and tables) by analogy. A simple mechanistic model for the stereochemical course of the addition of Li-3 to aldehydes and ketones is presented (Figure 6).

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Oxazolidine – Wikipedia,
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Awesome Chemistry Experiments For (R)-4-Benzyl-2-oxazolidinone

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The thiazolidinedione moiety of ciglitazone and its analogues can be replaced by an alpha-alkoxy or alpha-thioether carboxylic acid group. The influence of the nature of the R group, the length of the connector to the aromatic backbone of the molecule, and the stereochemistry have been studied. The most potent compounds have glucose-lowering activity at doses as low as 0.01 mg/kg.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1857NO – PubChem

 

Discovery of 22625-57-6

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The copper-catalyzed reaction of arylidenecyclopropanes (1) with 2-oxazolidinone (2) gave the corresponding homoallylic oxazolidinones (3) in good to high yields. For example, the reaction of diphenylmethylenecyclopropane (1a), {bis(p-tolyl)methylenecyclopropane (1b), and {bis(p-anisyl)methylene}-cyclopropane (1d) in the presence of 10 mol% of Cu(OTf)2 without solvent proceeded at 120C, giving the corresponding homoallylic oxazolidinones (3a, 3b, and 3d) in 89, 80, and 58% yields, respectively.

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Oxazolidine – Wikipedia,
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Awesome and Easy Science Experiments about 695-53-4

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The present invention provides a novel piperidine derivative and a tachykinin receptor antagonist containing same, as well as a compound represented by the formula:wherein R1 is carbamoylmethyl, methylsulfonylethylcarbonyl and the like; R2 is methyl or cyclopropyl; R3 is a hydrogen atom or methyl; R4 is a chlorine atom or trifluoromethyl; R5 is a chlorine atom or trifluoromethyl; and a group represented by the formula:is a group represented by the formula:wherein R6 is a hydrogen atom, methyl, ethyl or isopropyl; R7 is a hydrogen atom, methyl or a chlorine atom; and R8 is a hydrogen atom, a fluorine atom, a chlorine atom or methyl; or 3-methylthiophen-2-yl, and a salt thereof.

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Oxazolidine – Wikipedia,
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Naphthyridine compounds and their use as inhibitors of HPK1 are described. The compounds are useful in treating HPK1-dependent disorders and enhancing an immune response. Also described are methods of inhibiting HPK1, methods of treating HPK1-dependent disorders, methods for enhancing an immune response, and methods for preparing the naphthyridine compounds.

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Herein, we disclose that carboxylate phosphabetaine can act as a competent organocatalyst for promoting the intramolecular ring opening of oxetanes, delivering oxazolidin-2-ones in good to excellent yields. 1H NMR studies and DFT calculations revealed that the carboxylate moiety of the phosphabetaine not only acts as a proton shuttle, but also provides crucial hydrogen bonding for the activation of the oxetane ring.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1148NO – PubChem