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Sulfonyl bis-N-oxazolidinone (SBO): A new versatile dielectrophile with sequential reactivity

The sulfonylbis-N-oxazolidinone (SBO) was designed as a biscarbamoylating reagent Its synthesis was easily carried out starting from sulfuryl chloride, chlorosulfonyl isocyanate or sulfonylbis-isocyanate, using oxazolidinone and/or 2 -haloethanol in one-pot procedures. The structure of SBO was established by X-ray crystallography. The difference of reactivity of both electrophilic carbonyl centers allows the formation of dissymetric linkages.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H488NO – PubChem

 

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A novel 1beta-methylcarbapenem antibiotic, S-4661 synthesis and structure-activity relationships of 2-(5-substituted pyrrolidin-3-ylthio)-1beta-methylcarbapenems

The synthesis and biological activity of (1R,5S,6S)-2-[(3S,5S)-5-substituted pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acids are described. These compounds exhibit potent antibacterial activity against a wide range of both Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa. Of these new carbapenems, (1R,5S,6S)-2-[(3S,5S)-5-sulfamoylaminomethyl pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (S-4661) showed the most potent and well balanced activity and was selected as a candidate for further evaluation.

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Oxazolidine | C3H648NO – PubChem

 

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CuO nanoparticles catalyzed C-N, C-O, and C-S cross-coupling reactions: Scope and mechanism

CuO nanoparticles have been studied for C-N, C-O, and C-S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs 2CO3, and K2CO3 at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H656NO – PubChem

 

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The biological effects of structural variation at the meta position of the aromatic rings and at the end of the alkenyl chain in the alkenyldiarylmethane series of non-nucleoside reverse transcriptase inhibitors

In an effort to elucidate a set of structure-activity relationships in the alkenyldiarylmethane (ADAM) series of non-nucleoside reverse transcriptase inhibitors, a number of modifications were made at two locations: (1) the meta positions of the two aromatic rings and (2) the end of the alkenyl chain. Forty-two new ADAMs were synthesized and evaluated for inhibition of the cytopathic effect of HIV-1RF in CEM-SS cell culture and for inhibition of HIV-1 reverse transcriptase. The size of the aromatic substituents was found to affect anti-HIV activity, with optimal activity appearing with Cl, CH3, and Br substituents and with diminished activity occurring with smaller (H and F) or larger (I and CF3) substituents. The substituents at the end of the alkenyl chain were also found to influence the antiviral activity, with maximal activity associated with methyl or ethyl ester groups and with diminished activity resulting from substitution with higher esters, amides, sulfides, sulfoxides, sulfones, thioesters, acetals, ketones, carbamates, ureas, and thioureas. Twelve of the new ADAMs displayed submicromolar EC50 values for inhibition of the cytopathic effect of HIV-1RF in CEM-SS cells. Selected ADAMs, 19 and 21, were compared to previously published ADAMs 15 and 17 for antiviral efficacy and activity against the HIV-1 reverse transcriptase enzyme. All four ADAMs were found to inhibit HIV-1 reverse transcriptase enzyme activity, to inhibit the replication of a variety of HIV-1 clinical isolates representing syncytium-inducing, nonsyncytium-inducing, and subtype representative isolates, and to inhibit HIV-1 replication in monocytes. Subsequent assessment against a panel of site-directed reverse transcriptase mutants in NL4-3 demonstrated no effect of the K103N mutation on antiviral efficacy and a slight enhancement (6- to 11-fold) in sensitivity to AZT-resistant viruses. Additionally, ADAMs 19 (44-fold) and 21 (29-fold) were more effective against the A98G mutation (found in association with nevirapine resistance in vitro), and ADAM 21 was 5-fold and 2-fold more potent against the Y181C inactivation mutation than the previously reported ADAMs 15 and 17, respectively. All four ADAMs were tested for efficacy against a multidrug-resistant virus derived from a highly experienced patient expressing resistance to the reverse transcriptase enzyme inhibitors AZT, ddI, 3TC, d4T, foscarnet, and nevirapine, as well as the protease inhibitors indinavir, saquinavir, and nelfinavir. ADAM 21 was 2-fold more potent than ADAM 15 and 6-fold more potent than ADAMs 17 and 19 at preventing virus replication. Thus, we have identified a novel series of reverse transcriptase inhibitors with a favorable profile of antiviral activity against the primary mutation involved in clinical failure of non-nucleoside reverse transcriptase inhibitors, K103N, and that retain activity against a multidrug-resistant virus.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1156NO – PubChem

 

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Gold(l)-Catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles

“Chemical Equation Presented” A 1:1 mixture of [P(t-Bu) 2-obiphenyl]AuCl and AgSbF6 catalyzes the intermolecular amination of allylic alcohols with 1-methylimldazolidin-2one and related nucleophiles that, In the case of gamma-unsubstituted or gamma-methyl- substituted allylic alcohols, occurs with high gamma-regioselectivity and syn-stereoselectivlty.

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Method for producing cyclic carbamate ester

A method for producing a cyclic carbamate ester produces the cyclic carbamate ester by reacting an organic compound having at least two halogen atoms per molecule, an amine having at least two hydrogen atoms on a nitrogen atom, and carbon dioxide.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H142NO – PubChem

 

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Highly mesoporous and high surface area carbon: A high capacitance electrode material for EDLCs with various electrolytes

Activated carbon fibers (ACFs) with high surface area and highly mesoporous structure for electrochemical double layer capacitors (EDLCs) have been prepared from polyacrylonitrile fibers by NaOH activation. Their unique microstructural features enable the ACFs to present outstanding high specific capacitance in aqueous, non-aqueous and novel ionic liquid electrolytes, i.e. 371 F g-1 in 6 mol L-1 KOH, 213 F g-1 in 1 mol L-1 LiClO4/PC and 188 F g-1 in ionic liquid composed of lithium bis(trifluoromethane sulfonyl)imide (LiN(SO2CF3)2, LiTFSI) and 2-oxazolidinone (C3H5NO2, OZO), suggesting that the ACF is a promising electrode material for high performance EDLCs.

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Oxazolidine | C3H1146NO – PubChem

 

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Comparative life cycle assessment of potassium carbonate and monoethanolamine solvents for CO2 capture from post combustion flue gases

Carbon capture and storage (CCS) has the potential to enable significant reductions in carbon dioxide (CO2) emissions from stationary sources such as coal-fired power stations. The most advanced carbon capture technology is CO2 absorption using amine-based solvents, such as monoethanolamine (MEA). However, there is concern that the increased use of amine-based solvents will lead to other potential negative environmental impacts, such as increased human toxicity. The use of benign inorganic solvents, such as potassium carbonate, which do not degrade in the presence of oxygen or other impurities such as sulphurous or nitrous oxides offer significant advantages over amine-based solvents in terms of environmental impact. A comparative life cycle assessment (LCA) between the use of MEA and the CO2CRC’s potassium carbonate based UNO MK 3 technology for the capture of 1tonne of CO2 from a brown-coal fired power station has been completed. The results reveal that the UNO MK 3 process is significantly better than MEA on ecotoxicity and carcinogen emissions and substantially better on all other indicators. The benefits of the UNO MK 3 process compared with MEA are due to avoidance of emissions from MEA degradation along with the savings in energy use for CO2 removal. The significant environmental benefits of the UNO MK 3 process compared with MEA were not altered by an uncertainty analysis or sensitivity analysis of key inputs and assumptions.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H569NO – PubChem

 

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Immobilization of phosphorescent quantum dots in a sol-gel matrix for acetone sensing

Quantum dots (QDs) are semiconductor nanoparticles (NPs) that are increasingly used in optical sensing applications due to their exceptional optoelectronic properties. When such nanocrystals are doped with certain metal impurities, a phosphorescence-like emission can be obtained, allowing the development of novel robust and highly selective sensing phases (it is possible to perform time resolved measurements enabling a simple discrimination between the luminescence emission from the QDs from the background fluorescence of the sample, in which luminescent lifetime is shorter). In this context, a phosphorescent sensing material for acetone control in water media has been developed based on the immobilization of phosphorescent quantum dots in an inorganic sol-gel solid matrix. For such purpose, colloidal manganese-doped ZnS nanoparticles (Mn:ZnS QDs) surface-modified with l-cysteine (for water solubilisation) were synthesised. The Mn:ZnS QDs exhibit an intense room temperature phosphorescence (RTP) emission in aqueous media even in the presence of dissolved oxygen. Further, a simple and general procedure is proposed to incorporate the colloidal l-cysteine Mn:ZnS QDs in a sol-gel matrix. Application of the developed sensing material to analytical control of acetone dissolved in contaminated water samples was performed based on measurement of the quenching effect of the analyte on the QDs phosphorescence emission. The sol-gel procedure (e.g. nature and concentration of the silica precursors used) employed for immobilization of the QDs was optimized trying to obtain the best analytical features for detection of acetone. The optimized sensing material showed a high selectivity of the sensing material towards acetone. The linear range of the developed methodology turned out to be at least up to 50% acetone:water (v/v) with a detection limit (DL) for acetone dissolved in aqueous medium of 0.16% acetone:water (v/v). The developed sensing phase was finally applied for acetone determination in different spiked water samples, and the recoveries fall in the range of 93-109%.

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Oxazolidine | C3H1017NO – PubChem

 

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Synthesis and characterization of imine-palladacycles containing imidate “pseudohalide” ligands: Efficient Suzuki-Miyaura cross-coupling precatalysts and their activation to give Pd0Ln species (L = Phosphine)

Dinuclear palladacyclic complexes [{Pd(C^N)(mu-NCO)} 2] (C^N = N-phenylbenzaldimine, Phbz) containing asymmetric imidato units (-NCO- = succinimidate (succ; 1), phthalimidate (phthal; 2), maleimidate (mal; 3), 2,3-dibromomaleimidate (2,3-diBrmal; 4), glutarimidate (glut; 5)) have been readily prepared by reaction between the di-mu-acetate precursor and cyclic imide ligands in a 1:2 molar ratio. Base treatment of the less acidic ligands 2-oxazolidone and delta-valerolactame with KOH/MeOH was required to give analogous -NCO- bridged complexes (6 and 7). Reactions of the dinuclear complexes with tertiary phosphines provide novel mononuclear N-bonded imidate derivatives of the general formula [Pd(Phbz)(imidate)(PR3)] (R = Ph (a), 4-F-C6H4 (b), 4-MeO-C6H4 (c), CH2CH2CN (d)). The application of these novel palladacyclic complexes as precatalysts for the Suzuki-Miyaura cross-coupling reactions of both aryl and benzyl bromides with phenylboronic acid has been examined. The acetate adducts [Pd(Phbz)(CH 3COO)(PR3)] (8a,c) were prepared to assess the role of imidate ligands in catalyst performance. The mononuclear imidate derivatives possess greater activity than the parent dinuclear complexes, exhibiting comparable performance in the cross-coupling of benzyl bromide with arylboronic acids to the best examples reported in the literature. The mononuclear imidate derivatives give a common Pd0Ln intermediate, as inferred by the release of the organic fragment (first reductive elimination product). Catalyst activation occurs by reaction of phenylboronic acid with the palladacycle in the absence of exogenous base (as shown by GC-MS and ESI-MS), with implications for the reliable comparison of catalyst performance across a series of related precatalysts (e.g., how catalyst/reagents are mixed and what is their order of addition). The single-crystal X-ray structures of compounds 4, 7, 1d, 3c, and 8a have been determined.

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