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Several new methods for the synthesis of differently substituted 2-amidofurans are described. The thermolysis of furan-2-carbonyl azide results in a Curtius rearrangement and the resulting furanyl isocyanate was trapped with various organometallic reagents. A second method consists of a C-N cross-coupling reaction of a bromo-substituted furan with various amides, carbamates, and lactams. The CuI-catalyzed cross-coupling reaction between furanyl bromides and amides furnished 2- and 3-substituted amidofurans in 45-95% yield. The third protocol used involves the reaction of cyclic carbinol amides with triflic anhydride. The reaction proceeds under very mild conditions to provide alpha-(trifluoromethyl)sulfonamido-substituted furans in high yield. The resulting iminium ion derived from the reaction of the hydroxy pyrrolidinone with Tf2O undergoes a facile ring opening as a consequence of the adjacent hydroxyl group to produce an imino triflate intermediate. Subsequent cyclization of this highly electrophilic imine with the oxygen atom of the adjacent carbonyl group leads to an imino dihydrofuran that reacts further with another equivalent of Tf2O to give the observed product.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H879NO – PubChem

 

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2-Oxazolidinones are synthesized in high yield by oxidative carbonylation of beta-amino alcohols using salen-Co(II)/NaI or salen-Co(III)-I as a catalyst and using CO as the carbonyl source. Studies of functional group compatibility using a series of substituted salen-Co(II) or salen-Co(III)-I complexes demonstrate a broad tolerance of functionality during the carbonylation reaction.

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Novel types of compounds, N-tributylstannyl-2-oxazolidinone (4a) and tetrahydro-2H-1,3-oxazin-2-one (4b), are formed from the adduct of (n-Bu3Sn)2O (1) with omega-haloalkyl isocyanate (2), and the subsequent coupling reaction with alkyl halides gives a variety of N-substituted 2-oxazolidinones and tetrahydro-2-oxazinones in a one-pot procedure.Both the cyclization and the coupling reaction proceed quantitatively in the presence of HMPA which enhances the reactivity of the Sn-heteroatom bond by coordination.

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Reference:
Oxazolidine – Wikipedia,
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The present invention relates to certain substituted phenyl oxazolidinones and to processes for the synthesis of the same. This invention also relates to pharmaceutical compositions containing the compounds of the present invention as antimicrobials. The compounds are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria, for example, multiple-resistant staphylococci, streptococci and enterococci as well as anaerobic organisms, for example, Bacterioides spp. and Clostridia spp. species, and acid fast organisms, for example, Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H74NO – PubChem

 

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The first transition-metal-free carboarylation of alkynes with commercial and readily available alcohols as alkylating agents was realized in the presence of an environmentally benign calcium catalyst. Thereby, a novel protocol for the one-step synthesis of highly congested, all-carbon tetrasubstituted alkenes, as incorporated in potentially bioactive, complex dihydronaphthalene, chromene and dihydroquinoline structures, is provided. The reaction features an unprecedented, particularly wide substrate scope, good functional-group tolerance and simple experimental operation under mild reaction conditions. Finally free: The first transition-metal-free one-step synthesis of highly congested, all-carbon tetrasubstituted olefins has been realized by a calcium-catalyzed carboarylation reaction. Internal alkynes react with alcohols as alkylating reagent under mild reaction conditions, which provides access to a variety of useful structural scaffolds via highly reactive trisubstituted vinyl cations.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H530NO – PubChem

 

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Disclosed is a process for preparing an aryloxyalkylene amine compound via an aminoethylation reaction comprising: a) reacting an aromatic hydroxyl compound in the presence of a basic catalyst with a 2-oxazolidinone compound of the formula II to form an intermediate reaction product; wherein R3 is selected from the group consisting of hydrogen or lower alkyl having 1 to 6 carbon atoms, R4 is selected from the group consisting of hydrogen, straight or branched chain alkyl having from one to six carbon atoms, phenyl, alkaryl, or arylalkyl; and b) reacting the intermediate product of step a) with a polyalkylene polyamine.

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Quantitative online NMR spectroscopy was used for studying the species distribution in solutions of carbon dioxide in aqueous monoethanolamine (MEA) and diethanolamine (DEA). The mass fraction of the amine in the unloaded solution was 0.2 and 0.3 g/g, respectively, the carbon dioxide loading was up to 1.1 mo lC O2 / mo lamine, temperatures were between 293 and 353 K. A special apparatus was designed that allows preparing the mixtures gravimetrically and applying pressures up to 25 bar to keep the carbon dioxide in solution. It was coupled to a 400 MHz NMR spectrometer by heated capillaries. By using both 1H and 13C NMR spectroscopy quantitative information on the concentrations of the following species were obtained: amine, carbamate, bicarbonate, and carbon dioxide. Due to the fast proton transfer between molecular and protonated amine, only the sum of their concentrations can be determined. Furthermore, a byproduct, 2-oxazolidone, was observed and quantified. The experimental data were used for developing a thermodynamic model of the studied electrolyte solutions based on the extended Pitzer GE-model. In the model development, also vapor-liquid equilibrium data from the literature were included. The model gives reliable results both for the species distribution and the vapor-liquid equilibrium of the studied mixtures.

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A highly efficient copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with benzo[b]thiophene 1,1-dioxides as the dipolarophiles was developed, providing elegant access to novel chiral tricyclic pyrrolidine-fused benzo[b]thiophene 1,1-dioxide derivatives in good to excellent yields (up to 99%) with excellent diastereo- and enantioselectivities (up to >25:1 dr, up to 99% ee). Furthermore, the cycloadducts could be conveniently converted to synthetically important tricyclic pyrrolidine-fused benzo[b]thiophene and tetracyclic oxazolidin-2-one derivatives via simple transformations.

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Oxazolidine – Wikipedia,
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A study was conducted to evaluate the mechanical properties of low density fiberboard produced with combinations of two fibers soybean straw (Glycine max), and wheat straw (Triticum aestivum) and two resins methylene diphenyl diisocyanate (MDI) and epoxidized sucrose soyate (ESS) resin as binders. ESS is a high performance, soybean oil based epoxy that has shown promise as a highly biobased adhesive. Six formulations of panels were produced using various combinations of straw and resin binder. Mechanical testing of sample boards was conducted using ASTM standard D1037-12. Test results showed that type of resin did not influence soy straw or wheat straw board’s stiffness and strength properties but had a major impact on water resistance, screw withdrawal strength and internal bond strength. The study demonstrated the potential of ESS as a novel binder for fiberboard system if a suitable crosslinker and catalyst is utilized. It also showed that increasing ESS content over 50% in a MDI blend lowered the performance characteristics of boards. However, analytical testing of the resin systems showed limited reactivity between ESS soyate and MDI, indicating other compatible resin chemistries should be explored for achieving superior board properties. Overall, a resin blend with 25?50% ESS in MDI appears favorable for low density fiberboards. ESS can be a promising bio-based resin as it has the potential to meet California Air and Resources Board (CARB) standards while providing acceptable properties as an adhesive.

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Oxazolidine – Wikipedia,
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Trimethylsylil trichloroacetate (1) is a convenient reagent for the silylation of phenols, carboxylic acids, mercaptans, amides, acetylenes, and beta-keto esters, while the reaction of 1 with aldehydes and ketones affords silylated trichloromethyl carbinols (5).

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