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Catalytic one-pot synthesis of 4-(hetero)aryl substituted 5-(2-oxoethyl) oxazol-2(3: H)-ones by coupling-isomerization-elimination (CIE) sequence

N-Boc protected 1-aryl propargyl carbamates and acid chlorides can be readily transformed in a one-pot fashion by a coupling-isomerization-elimination (CIE) sequence into 4-substituted 5-(2-oxoethyl) oxazol-2(3H)-ones in moderate to good yield.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H560NO – PubChem

 

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2018 WSES/SIS-E consensus conference: Recommendations for the management of skin and soft-tissue infections

Skin and soft-tissue infections (SSTIs) encompass a variety of pathological conditions that involve the skin and underlying subcutaneous tissue, fascia, or muscle, ranging from simple superficial infections to severe necrotizing infections. SSTIs are a frequent clinical problem in surgical departments. In order to clarify key issues in the management of SSTIs, a task force of experts met in Bertinoro, Italy, on June 28, 2018, for a specialist multidisciplinary consensus conference under the auspices of the World Society of Emergency Surgery (WSES) and the Surgical Infection Society Europe (SIS-E). The multifaceted nature of these infections has led to a collaboration among general and emergency surgeons, intensivists, and infectious disease specialists, who have shared these clinical practice recommendations.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H956NO – PubChem

 

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Synthesis, characterization and properties of novel thermally stable poly(urethane-oxazolidone) elastomers

Oxazolidone-incorporated polyurethane elastomers based on hydroxyl terminated polycaprolactone, were synthesized and characterized. Reaction of epoxy-terminated polyurethane with isocyanate librated from a blocked polyisocyanate was the strategy followed. The reaction condition was optimized through preparation of model oxazolidones. Epoxy-terminated polyurethanes were prepared from reaction of glycidol with NCO-terminated polyurethane prepolymers and curing agent was synthesized from the reaction of trimethylol propane, toluene diisocyanate and N-methyl-aniline. Incorporation of heterocyclic oxazolidone groups into the polyurethane backbone caused improvements in thermal and mechanical properties. Investigation of structure-property relationship for prepared elastomers showed that the main determining factors for observed properties were crosslink density, crystallinity and content of oxazolidone rings.

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Oxazolidine | C3H1176NO – PubChem

 

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Bismuth- and Iron-Catalyzed Three-Component Synthesis of alpha-Amino Acid Derivatives: A Simple and Convenient Route to alpha-Arylglycines

Efficient bismuth- and iron-catalyzed three-component syntheses of alpha-arylglycines have been developed. These methods provide a general, atom-economic route to various N-protected alpha-arylglycines starting from readily available amides (or carbamates), glyoxalates, and (hetero)arenes with water as the only by-product. Scope and limitations of bismuth- and iron-catalyzed reactions are discussed and compared. In addition, mechanistic investigations as well as initial forays into stereoselective three-component reactions are presented.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H582NO – PubChem

 

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Asymmetric beta-boration of alpha,beta-unsaturated N -acyloxazolidinones by [2.2]paracyclophane-based bifunctional catalyst

An efficient copper-catalyzed asymmetric conjugate boration has been achieved by exploiting a new planar and central chiral bicyclic triazolium ligand. This protocol was highly efficient and gave a variety of chiral secondary alkylboronates in 97-99% ee. A preliminary mechanistic study supports the bifunctional nature of the catalyst.

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Flexible aliphatic poly(isocyanurate-oxazolidone) resins based on poly(ethylene glycol) diglycidyl ether and 4,4?-methylene dicyclohexyl diisocyanate

New flexible aliphatic oxazolidone-isocyanurate networks (AISOX) are obtained by reacting a low molecular weight diisocyanate (4,4?-methylene dicyclohexyl diisocyanate, H12MDI) and a macro-diepoxyde (poly(ethylene glycol) diglycidyl ether, Mn = 526, PEGDGE) in different molar ratio. The curing reaction, carried out from 25 C to 200 C, is studied by using DSC and FTIR. The effect of the molar ratio of the two monomers on thermal and mechanical properties of AISOX resins is investigated by DSC, thermogravimetric analysis, stress-strain measurements and optical microscopy. Independently from the feed composition, it is observed that the reaction steps are: (i) partial hydrolysis of isocyanate caused by water traces, (ii) incomplete trimerization of isocyanate to give isocyanurate, and (iii) formation of oxazolidone and complete conversion of isocyanate. At the highest concentration of the soft macrodiepoxyde (PEGDGE), the AISOX resin is in the rubbery state at room temperature and shows an elastomeric behavior.

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Synthesis and X-ray structure of a C5-C4-linked glucofuranose-oxazolidin-2- one

The formation of (4R)-4-carbamoyl-4-[(4R)-3-O-benzyl-1,2-O-isopropylidene- beta-L-threofuranos-4-C-yl]- oxazolidin-2-one instead of expected imidazolidin-2,4-dione (hydantoin) derivative from 5-amino- 5-cyano-5-deoxy-3-O- benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose or 3-O-benzyl-1,2-O- isopropyli-dene- alpha-D-xylo-hexofuranos-5-ulose under Bucherer-Bergs reaction conditions is reported. Single crystal X-ray diffraction data revealed that 3T4 is the prefered conformation for the furanose ring, while E2 and 2T1 conformations are adopted by the 1,3-dioxolane and 2-oxazolidinone five-membered rings, respectively.

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Oxazolidine | C3H1023NO – PubChem

 

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A and tin ycin A fully synthetic method (by machine translation)

The invention relates to a and tin ycin A fully synthetic method, the method consists in the compound (S)- 3 – ((S)- 1 – amino – 3 – methyl-butyl) – 8 – hydroxy isoflavone chroman – 1 – one with compound (2S, 3S, 4S) – 2 – amino – 4 – (benzyloxycarbonyl amino) – 6 – (uncle butoxy) – 3 – ((tert-butyl dimethyl) oxy) – 6 – oxo caproic acid by condensation reaction to obtain the key intermediate (3S, 4S, 5S) – 5 – azido – 3 – (benzyloxycarbonyl amino) – 4 – hydroxy – 6 – ((1 – (8 – hydroxy – 1 – isoindole chroman – 3 – yl) – 3 – methyl-butyl) amino) – 6 – butyl oxo caproic acid uncle; and then sequentially through the hydrogenation reduction, the cyclization reaction, takes off uncle butyl dimethyl silicon ether reaction, hydrolysis reaction to obtain ohwada ycin A. The method of the invention with the raw materials are easy, simple operation, low cost and the like, the resulting product ohwada cephalosporin A has broad spectrum bacterial inhibiting activity and anti-tumor activity. (by machine translation)

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Oxazolidine – Wikipedia,
Oxazolidine | C3H227NO – PubChem

 

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Integrated CO2 capture-fixation chemistry via interfacial ionic liquid catalyst in laminar gas/liquid flow

Simultaneous capture of carbon dioxide (CO2) and its utilization with subsequent work-up would significantly enhance the competitiveness of CO2-based sustainable chemistry over petroleum-based chemistry. Here we report an interfacial catalytic reaction platform for an integrated autonomous process of simultaneously capturing/fixing CO2 in gas-liquid laminar flow with subsequently providing a work-up step. The continuous-flow microreactor has built-in silicon nanowires (SiNWs) with immobilized ionic liquid catalysts on tips of cone-shaped nanowire bundles. Because of the superamphiphobic SiNWs, a stable gas-liquid interface maintains between liquid flow of organoamines in upper part and gas flow of CO2 in bottom part of channel. The intimate and direct contact of the binary reagents leads to enhanced mass transfer and facilitating reactions. The autonomous integrated platform produces and isolates 2-oxazolidinones and quinazolines-2,4(1H,3H)-diones with 81-97% yields under mild conditions. The platform would enable direct CO2 utilization to produce high-valued specialty chemicals from flue gases without pre-separation and work-up steps.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1101NO – PubChem

 

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Highly stereocontrolled synthesis of the 1beta-methylcarbapenem key intermediate by the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with a 4-acetoxy-2-azetidinone

The key synthetic intermediate (4) of 1beta-methylcarbapenems (1~3) was efficiently synthesized by employing highly stereocontrolled Reformatsky reaction (C4-alkylation) of 3-(2-bromopropionyl)-2-oxazolidone derivatives (6) with (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidino ne (5) in the presence of zinc dust followed by removal of 2-oxazolidone moieties. The best diastereoselectivity (beta:alpha = 95:5) could be realized by uses of sterically crowded achiral 2-oxazolidone derivatives such as 4,4-dimethyl-, 4,4,5,5-tetramethyl, and 4,4-dibutyl-5,5-pentamethylene-2-oxazolidone and higher reaction temperatures (refluxing tetrahydrofran). The remarkable diastereoselectivities observed for the Reformatsky reactions could be explained by means of the weakly chelating transition state models.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H649NO – PubChem