N-Substituted Oxazolidinediones

Shapiro, Seymour L.; Rose, Ira M.; Testa, Frank C.; Roskin, Eric; Freedman, Louis

doi:10.1021/ja01533a042

Cited by 27 publications

(15 citation statements)

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“…The oxazolidine moiety is an important building block for pharmacologically active compounds such as anti-diabetic [1], anti-tubercular [2], anti-convulsant [3] and aldose reductase inhibitors [4]. It is called pseudo-proline to mimic the proline skeleton for investigation of peptide biological activity [5].…”

Section: Introductionmentioning

confidence: 99%

“…In order to extend the chemistry of the oxazolidines, we have recently reported two complexes of cadmium and mercury with 2-(2-(pyridin-2-yl)oxazolidin-3-yl)ethanol (AEPC, scheme 1) [11] and in this work, coordination of this ligand to both copper halides and thiocyanate are described. Based on the X-ray analysis, the AEPC ligand converts to the other structures during complexation to the copper(I/II) halides (Cl, I) while keeping its base in treatment with Cu(NO 3 In addition to the expected biological properties of AEPC, binding the copper(II) ion to this unit makes these complexes a good choice for biologically active compounds. The copper(II) provides a rapid anti-microbial action without the risk of resistance development [12] and, at the same time, has the ability to modulate angiogenesis, a crucial challenge of current tissue engineering technologies.…”

Section: Introductionmentioning

confidence: 99%

“…ConclusionIn this work, four complexes of copper(I/II), [Cu(AEPC)(NCS) 2 ] (1), AEPC = 2-(2-(pyridin-2yl)oxazolidin-3-yl)ethanol, [Cu(DEA)Cl 2 ] (2), DEA = diethanolamine, [Cu(BHEG) 2 ] (3), BHEG = bis(2-hydroxyethyl)glycinato, were synthesized in a reaction between AEPC with Cu(NO 3 ) 2 /KSCN mixture (1) and copper(I/II) halides(2,3). Their spectral (IR, UV-Vis, 1 H NMR) and structural (single crystal X-ray diffraction) properties were investigated.…”

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confidence: 99%

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Structural conversion of an oxazolidine ligand upon treatment with copper(I) and (II) halides; structural, spectral, theoretical and docking studies

Mardani

Golsanamlou

Jabbarzadeh

et al. 2018

Journal of Coordination Chemistry

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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Structural conversion of an oxazolidine ligand upon treatment with copper(I) and (II) halides; structural, spectral, theoretical and docking studies

Mardani

Golsanamlou

Jabbarzadeh

et al. 2018

Journal of Coordination Chemistry

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“…As a result of this hydrolysis, both compounds 2‐[(aminocarbonyl)oxy]‐2‐methyl‐propanoic acid (I) and 2‐hydroxy‐2‐methylpropanamide (II) can be formed, although the literature indicates that there is a greater preference for the formation of compound II …”

Section: Results and Mechanismmentioning

confidence: 99%

N-Chlorination rate of five-membered heterocyclic nitrogen compounds

Pastoriza

Antelo

Amoedo

et al. 2016

J. Phys. Org. Chem.

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aThe kinetics of N-chlorination reaction of pyrrolidine, pyrrolidone, succinimide, 5,5,-dimethyloxazolidine-2,4-dione, 5,5-dimethylhydantoin and 1-hydroximethyl-5,5-dimethylhydantoin with HOCl in aqueous solution were studied at 25°C, constant ionic strength and under isolation conditions in a wide pH range. The set of compounds studied in this paper is characterized by having different functional groups and the same cyclic structure, consisting of a five-member ring with a nitrogen atom in the ring, which is susceptible to be chlorinated. This series of compounds covers nine pK a units, and the kinetic studies allow us to know, like, the presence of an amino, amide or imide group modify the reactivity of nitrogenous compound.Experimental data were fitted to the first-order kinetic equation. All reactions were found to be of first order in both HOCl and nitrogenous compound concentration. Kinetics studies demonstrate that some of these compounds are hydrolyzed in alkaline medium. In each case, reaction mechanism in agreement with the experimental results is proposed. The results were compared with other compounds with similar cyclic structure (2-oxazolidinone and proline).

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“…3,4 The compounds were synthesized by the reaction of 0.01-0.05 mole (S)-(-)-ethyl lactate and an equimolar amount of the o-aryl isocyanate in the presence of sodium metal in toluene (Scheme 2).…”

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confidence: 99%

Conformational preferences in diastereomeric(5S)‐methyl‐3‐(o‐aryl)‐2,4‐oxazolidinediones

Demir

Doğan

2003

Chirality

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The thermally interconvertible diastereomers of the (5S)-methyl-3-(o-aryl)-2,4-oxazolidinediones were synthesized and their conformers studied by (1)H NMR and HPLC. The barriers to rotation about the N-C(aryl) bond were found to be very much solvent dependent. For the o-fluoro oxazolidinedione, difference in barriers to rotation in deuterated methanol and deuterated chloroform amounted to 34 kJ/mol. ortho-Bromo substitution increased the barrier to rotation up to 100 kJ/mol in ethanol, which enabled the analytical separation of the diastereomers and observation of the thermodynamic enrichment of the S-P conformer by HPLC. In CDCl(3) by (1)H NMR, on the other hand, a barrier of only 89 kJ/mol was determined. The S-M and S-P conformers of the diastereomers of o-methyl, alpha-naphthyl and o-iodo derivatives have been assigned by NOESY experiments and the kinetic and thermodynamic constants for the interconversion between the S-M and S-P conformers were determined.

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N-Substituted Oxazolidinediones

Cited by 27 publications

References 0 publications

Structural conversion of an oxazolidine ligand upon treatment with copper(I) and (II) halides; structural, spectral, theoretical and docking studies

Structural conversion of an oxazolidine ligand upon treatment with copper(I) and (II) halides; structural, spectral, theoretical and docking studies

N-Chlorination rate of five-membered heterocyclic nitrogen compounds

Conformational preferences in diastereomeric(5S)‐methyl‐3‐(o‐aryl)‐2,4‐oxazolidinediones

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