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(S)-4-isopropyl-5,5-diphenyloxazolidin-2-one

(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one has been synthesized for the first time by the enantiospecific oxidative carbonylation of commercially available (S)-2-amino-3-methyl-1, 1-diphenylbutan-1-ol. The cyclocarbonylation reaction was carried out at 100?C in 1,2-dimethoxyethane (DME) as the solvent for 15 h, under 20 atm of a 4:1 mixture of CO?air and in the presence of the catalytic system PdI2/KI (substrate:KI:PdI2 molar ratio = 100:10:1), to give the oxazolidinone derivative in 81% isolated yield.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H788NO – PubChem

 

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Dendritic bis(oxazoline)copper(II) catalysts. 2. Synthesis, reactivity, and substrate selectivity

A series of dendritic bis(oxazoline) ligands 1-4 were synthesized to evaluate the effects of the degree of branching of a dendritic sector on both the reactivity and selectivity of their corresponding copper(II) complex- catalyzed Diels-Alder reaction between cyclopentadiene and a crotonyl imide. Kinetic studies unveiled a two-step mechanism of the Diels-Alder reaction, in which a reversible binding of the dienophile to the copper complex was followed by a rate-determining reaction between the resulting dienophile- catalyst complex with the diene. Furthermore, two interesting features emerged: first, the formation constant of the dienophile-catalyst complex decreased gradually on going from the lower to higher generations, and secondly, while the Diels-Alder reaction rate constant remained essentially the same from the zeroth to second generation catalysts, it dropped abruptly for the third generation one. These observations were rationalized as a consequence of a folding-back of the dendritic sectors toward the catalytic unit at the third generation, so that increase in steric size impeded both the reactivity and binding profiles of the catalytic system. This behavior was reminiscent of related phenomena observed by others from solvatomatic, photophysical, and viscosity studies. In line with this reasoning, a slight but noticeable substrate selectivity was observed for the third generation catalyst, which was absence for the lower ones, in competitive kinetic studies involving two dienophiles of different steric sizes.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H440NO – PubChem

 

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Compound design guidelines for evading the efflux and permeation barriers of Escherichia coli with the oxazolidinone class of antibacterials: Test case for a general approach to improving whole cell Gram-negative activity

Previously we reported the results from an effort to improve Gram-negative antibacterial activity in the oxazolidinone class of antibiotics via a systematic medicinal chemistry campaign focused entirely on C-ring modifications. In that series we set about testing if the efflux and permeation barriers intrinsic to the outer membrane of Escherichia coli could be rationally overcome by designing analogs to reside in specific property limits associated with Gram-negative activity: i) low MW (<400), ii) high polarity (clogD7.4 <1), and iii) zwitterionic character at pH 7.4. Indeed, we observed that only analogs residing within these limits were able to overcome these barriers. Herein we report the results from a parallel effort where we explored structural changes throughout all three rings in the scaffold for the same purpose. Compounds were tested against a diagnostic MIC panel of Escherichia coli and Staphylococcus aureus strains to determine the impact of combining structural modifications in overcoming the OM barriers and in bridging the potency gap between the species. The results demonstrated that distributing the charge-carrying moieties across two rings was also beneficial for avoidance of the outer membrane barriers. Importantly, analysis of the structure-permeation relationship (SPR) obtained from this and the prior study indicated that in addition to MW, polarity, and zwitterionic character, having ?4 rotatable bonds is also associated with evasion of the OM barriers. These combined results provide the medicinal chemist with a framework and strategy for overcoming the OM barriers in GNB in antibacterial drug discovery efforts. Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Electric Literature of 497-25-6. In my other articles, you can also check out more blogs about 497-25-6

Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1019NO – PubChem

 

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Platinum-catalyzed intermolecular hydroamination of vinyl arenes with carboxamides

(Chemical Equation Presented) Reaction of benzamide with 4-methylstyrene catalyzed by a 1:2 mixture of [PtCl2(H2C=CH 2)]2 and P(4-C6H4CF 3)3 (5 mol %) in mesitylene at 140 C for 24 h led to the isolation of N-(1-p-tolylethyl)benzamide in 85% yield. Electron-rich, electron-poor, and hindered vinyl arenes underwent Markovnikov hydroamination with a range of carboxamides and amide derivatives in moderate to good yield with excellent regioselectivity.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H916NO – PubChem

 

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Preparation and Complex Formation of Polymers Anchoring 2-Oxazolidinone

Polymers anchoring 3-unsubstituted 2-oxazolidinone were prepared and their complex formation with phenol and mercury(II) acetate were investigated.Preformed poly(4-hydroxystyrene) was treated with tris(2,3-epoxypropyl)isocyanurate to give a polymer containing 2-oxazolidinone residues within the limits of 57.7 molpercent.Polymers carrying 2-oxazolidinone were also prepared through the homopolymerization and copolymerization of 4-(2-oxo-5-oxazolidinylmethoxy)phenyl acrylate.The effective concentration of 2-oxazolidinone residue in the polymers, which is accessible to phenol, was determined on the assumption that the polymer-bound 2-oxazolidinone and phenol formed a 1:1 complex. 2-Oxazolidinone and a mercury atom formed a 2:1 complex; this relation on the molar ratio applies to all forms of complexes between the mercury atom and the 2-oxazolidinone residue in the polymers.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H643NO – PubChem

 

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Synthesis of cyclic carbonates from urea and diols over metal oxides

Several metal oxides were used for synthesis of ethylene carbonate from urea and ethylene glycol. ZnO showed high activity towards the reaction. TPD, FTIR and reaction test indicated that the catalysts with appropriate acid and base properties were favorable to the synthesis of cyclic carbonate. Furthermore, the reaction of urea with various diols revealed that the selectivity of five-membered cyclic carbonates was higher than that of six-membered cyclic carbonates.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H741NO – PubChem

 

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Preparation of N-akenylcarbamic esters

N-Alkenylcarbamic esters of the general formula I STR1 where at least one of the R1 radicals is hydrogen and the second R1 radical is hydrogen or C1 -C4 –alkyl, the R2 radical is an aliphatic, cycloaliphatic, araliphatic or aromatic radical which can be linked to the R3 radical to form a 2- to 10-membered bridge, and the R3 radical is an aliphatic, cycloaliphatic or aromatic radical, from an alkenyl carboxylate of the general formula II STR2 where R1 has the abovementioned meaning, and R4 is hydrogen, an aliphatic, cycloaliphatic or aromatic radical, and a carbamic ester of the general formula III STR3 where the R2 and R3 radicals have the abovementioned meanings, are prepared by reacting the starting compounds in the presence of a base.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H119NO – PubChem

 

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Asymmetric Intramolecular Ene Reaction Catalyzed by a Chiral Titanium Reagent and Synthesis of (-)-epsilon-Cadinene

A highly diastereo- and enantio-selective intramolecular ene reaction was developed by employing a chiral titanium reagent generated in situ from TiCl2(OPri)2 and a tartrate-derived chiral 1,4-diol.This reaction afforded masked cyclohexanone and cyclopentanone derivatives with high optical purities which were synthetically useful chiral building blocks.From the intramolecular ene product (-)-epsilon-cadinene was synthesized by the use of the newly developed intramolecular Michael reaction.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H856NO – PubChem

 

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Efficient chiral monophosphorus ligands for asymmetric Suzuki-Miyaura coupling reactions

A series of novel P-chiral monophosphorus ligands exhibit efficiency in asymmetric Suzuki-Miyaura coupling reactions, enabling the construction of an array of chiral biaryl products in high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. The carbonyl-benzooxazolidinone moiety in these chiral biaryl products allows facile derivatization for further synthetic applications. A computational study has revealed that a pi-pi interaction between the two coupling partners can enhance the enantioselectivity of the coupling reaction.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1046NO – PubChem

 

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1,3-Dipolar cycloaddition of N-substituted dipolarophiles and nitrones: Highly efficient solvent-free reaction

(Chemical Equation Presented) New isoxazolidines were synthesized in good to excellent yields by 1,3-dipolar cycloaddition of N-vinylamide dipolarophiles and nitrones. Strikingly, solvent-free conditions gave high conversion and yields, shortened reaction time, and minimized degradation products. N-Vinyloxazolidin-2-one and its analogues used in these cycloaddition reactions were conveniently prepared in excellent yields by a modified version of Buchwald’s one-step copper-catalyzed vinylation using vinyl bromide. From the adducts, a two-step access to various unsymmetric aspartate derivatives was also described.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1051NO – PubChem