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Efficient and general procedures for the cross-coupling of 1,1-dibromoalkenes and N-, O-, and P-nucleophiles are reported. Fine-tuning of the reaction conditions allows for either site-selective, double, or alkynylative cross-coupling, therefore providing divergent and straightforward entries to numerous building blocks such as bromoenamides, ynamides, ketene N,N-acetals, bromoenol ethers, ynol ethers, ketene O,O-acetals, or vinylphosphonates and further expanding the copper catalysis toolbox with useful and versatile processes.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H672NO – PubChem

 

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This review is an attempt to give an overview on the recent advances and developments in the synthesis of 2-oxazolidinone frameworks through carbon dioxide (CO2) fixation reactions under solvent-free conditions. The cycloaddition of CO2 to aziridine derivatives is discussed first. This is followed by carboxylative cyclization of N-propargylamines with CO2 and three-component coupling of epoxides, amines, and CO2. Finally, cycloaddition of CO2 to propargylic alcohols and amines will be covered at the end of the review. The literature has been surveyed up until the end of 2018.

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A scale of solute hydrogen-bond acidity has been constructed using equilibrium constants (as log K values) for complexation of series of acids (i) against a given base in dilute solution in tetrachloromethane, equation (A). Forty-five such equations have been solved to yield LB and DB log Ki = LB log KAHi +DB (A) values characterising the base, and log KAH values that characterise the acid. In this analysis, use has been made of the novel observation that all the lines in equation (A) intersect at a given point where log K = log KAH = -1.1 with K on the molar scale. Some 190 log KAH values that constitute a reasonably general scale of solute hydrogen-bond acidity have been obtained. It is shown that there is no general connection between log KAH and any proton-transfer quantities, although certain family dependences are obtained. A number of acid-base combinations are excluded from equation (A), and alternative log KAHE values have been determined for such cases. The general log KAH values may be transformed into alpha2H values suitable for use in multiple linear-regression analysis through the equation alpha2H = (log KAH +1 .1 )/4.636.

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Oxazolidine – Wikipedia,
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The present invention is directed to tricyclic compounds of formula (I) which are inhibitors of one or more mutant IDH enzymes: (I). The present invention is also directed to uses of the tricyclic compounds described herein in the potential treatment or prevention of cancers in which one or more mutant IDH enzymes are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such cancers.

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Oxazolidine – Wikipedia,
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A compound of formula (I) as well as pharmaceutically acceptable salt thereof, wherein R1 to R5 have the significance given in claim 1, can be used as a medicament.

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We demonstrate here, a new polystyrene supported Cu(ii) catalyzed proficient synthetic methodology for the facile N-arylation of aromatic, aliphatic, cyclic and heterocyclic amides with aryl halides under neat conditions. The catalyst, PS-Cu(ii)-ala, was prepared through the grafting of copper metal on a polystyrene-beta-alanine imine network. The catalyst shows a wide range of substrate scope and excellent functional group tolerance, and produces the desired anilides in mostly high yields. The material is thoroughly characterized by DRS-UV, FT-IR, AAS, FE-SEM, TGA analysis and energy dispersive X-ray (EDX) studies. The catalyst can be easily recovered from the reaction medium and reused without significant loss of its catalytic activity suggesting future potential of this catalyst.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H646NO – PubChem

 

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A highly enantioselective Rh-catalyzed addition of arylboronic acids to non-benzofused five-membered cyclic N-sulfonyl alkyl-substituted ketimines has been developed. With simple chiral sulfur-olefin as the ligand, the reaction allows convenient access to a variety of sulfamidates with uniformly excellent enantioselectivities (97-99% ee). The synthetic utility of this protocol was exemplified by rapid asymmetric construction of tetrasubstituted chiral beta-amino alcohols and their derivatives.

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Oxazolidine – Wikipedia,
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ConspectusThe cathodic reduction of acetonitrile solutions containing a tetraalkylammonium salt leads to the formation of the cyanomethyl anion (-CH2CN, cyanomethanide). This electrolysis can be carried out under very simple experimental conditions (constant-current electrolyses), using various cathodic materials, controlling the amount of base by simply controlling the amount of charge. Despite the fact that the mechanism for this electrochemical reaction is still debated (and it depends on the cathodic material), the outcome of the electrolysis is the formation of a strong base, -CH2CN (pKa 31.3 for acetonitrile in DMSO).The chemical behavior of this electrogenerated base (EGB) strongly depends on its counterion, which in this case is a tetraalkylammonium cation, with a low charge density and thus not coordinated. The very weak interaction between R4N+ and -CH2CN renders the cyanomethyl anion a “naked” ion, and thus highly reactive. In particular, the cyanomethyl anion can react as a base and as a nucleophile. In the first case, it behaves as a strong base and, after deprotonation of a weak acidic substrate, transforms itself into a solvent molecule, acetonitrile, thus generating no byproducts. In the second case, the reactivity as a nucleophile of the cyanomethyl anion obviously depends on the reaction partner. When an electrophile is present in the reaction mixture, a cyanomethylation is obtained (e.g., with aromatic aldehydes, possessing no acidic hydrogen atoms, which undergo nucleophilic attack on the carbonyl carbon atom by -CH2CN); on the contrary, when no reagent is present other than acetonitrile and tetraalkylammonium salt, an attack on the parent molecule leads to the acetonitrile dimer, 3-aminocrotononitrile, which in turn can behave as a base and/or as a nucleophile. In this regard, some authors report that it is preferable to carry out the electrogeneration of the cyanomethyl anion under different experimental conditions, i.e., using an undivided cell and a sacrificial magnesium anode. In this way, a Grignard-type reagent is formed (Mg(CH2CN)2) which highly stabilizes the cyanomethyl anion, preventing its dimerization. It should be noted that in our laboratory the electrogenerated tetraalkylammonium cyanomethanide was extensively used in various reactions (both acid-base and nucleophile-electrophile, vide infra), and in almost no case, the amount of acetonitrile dimer formed exceeded 5%, confirming the validity of this electrochemical methodology to generate a very efficient base. Moreover, when in the reaction mixture both a weak acid and an electrophile are present, the prevalent reactivity of the cyanomethyl anion is as a base, leaving the possibility of a cyanomethylation reaction to those cases in which no acidic substrate is present. We have successfully used the electrogenerated cyanomethyl anion in many base-induced reactions, as the synthesis of the beta-lactam ring (chiral or not), the insertion of carbon dioxide into amines and amino alcohols, the activation of elemental sulfur and insertion into carbonyl compounds, the selective alkylation of difunctional compounds, etc.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H437NO – PubChem

 

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Catalytic cross double carbonylation of secondary amines and alcohols proceeds in the presence of [PdCl2(MeCN)2] and CuI under carbon monoxide (80 atm) and oxygen (5 atm). Catalytic intramolecular double carbonylation of beta-amino alcohols gives morpholine-2,3-diones, which are excellent protecting compounds of amino alcohols and important precursors for biologically active nitrogen compounds. In contrast, catalytic single carbonylation of beta-amino alcohols under a mixture (1 : 1) of carbon monoxide and oxygen (1.0 atm) proceeds to give oxazolidin-2-ones selectively. The reaction can be explained by assuming a mechanism which includes intramolecular nucleophilic attack of the hydroxy group of (hydroxyethyl)aminocarbonyl ligands on the CO ligand of the carbamoylpalladium(II) complexes, followed by reductive elimination to give morpholine-2,3-diones. In contrast, direct nucleophilic attack of the hydroxy group to the carbamoyl group affords oxazolidin-2-ones. As a common intermediate for the double and single carbonylations, carbamoylpalladium(II) complex has been isolated by the reaction of [PdCl2(PMe3)2] with beta-amino alcohol under CO. The present double carbonylation of amino alcohols provides a novel and convenient method for synthesis of alpha-oxo carboxylic acids. Thus, the morpholine-2,3-diones obtained undergo reaction with Grignard reagents chemoselectively at the ester positions to give 2-substituted 2-hydroxymorpholin-3-ones, which undergo acid hydrolysis to give alpha-oxo carboxylic acids.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H636NO – PubChem

 

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With a global production of around 18 million tons (6th among all polymers) and a wide range of applications, such as rigid and soft foams, elastomers, coatings, and adhesives, polyurethanes (PUs) are a major polymer family. Nevertheless, they present important environmental and health issues. Recently, new and safer PUs, called non-isocyanate polyurethanes (NIPUs), have become a promising alternative to replace conventional PUs. Sustainable routes towards NIPUs are discussed herein from the perspective of green chemistry. The main focus is on the reaction between biobased carbonates and amines, which offers an interesting pathway to renewable polyhydroxyurethanes (PHUs). An overview of different routes for the synthesis of PHUs draws attention to the green synthesis of cyclic carbonate (CC) compounds and the aminolysis reaction. Current state-of-the-art of different biobased building blocks for the synthesis of PHUs focuses on CC compounds. Three classes of compounds are defined according to the feedstock: 1) vegetable fats and oils, 2) starch and sugar resources, and 3) wood derivatives. Finally, biobased PHU properties are discussed.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H402NO – PubChem