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We present here carbon-nitrogen bond formation via a coupling reaction of 2-iodo-selenophene catalyzed by Cu(I) in the presence of a base and an inexpensive ligand, and establish the first route to obtaining 2-nitrogen-selenophene derivatives in good yields. We can anticipate that this reaction works well with oxazolidinones, lactams, and aliphatic and aromatic amides, as nitrogen sources, in the absence of any supplementary additives. In addition, the reaction proceeded cleanly under mild reaction conditions and was sensitive to the ratio of amide/2-iodo-selenophene, as well as the nature of the ligand, base, and solvent.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H496NO – PubChem

 

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Isocyanurate?oxazolidone (ISOX) polymers have been reported as a novel, intrinsically self-healable thermoset, and their healing mechanism under the effect of nucleophiles, such as tertiary amines and pyridines during polymerization, is thoroughly investigated in this study. This work provides evidence that the healing behavior of the polymers results part from the transformation of isocyanurate to oxazolidone on the fracture surfaces of the ISOX polymers at elevated temperatures. The isocyanurate transformation is characterized by chemical composition of the ISOX polymers before and after a predetermined healing procedure, through a combination characterization of Fourier transform infrared spectroscopy and carbon nuclear magnetic resonance spectroscopy. From the chemical composition of the ISOX polymers, an increased oxazolidone fraction is observed after the healing event, which verifies the hypothesized healing mechanism. By correlating the change in oxazolidone fraction in the polymers during the healing event, with the corresponding healing performance of the polymers, healing efficiencies of the polymers are shown to be inversely proportional to the ratio of oxazolidone to isocyanurate in the polymers. The transformation to oxazolidone is also shown to be dependent on two variables, nucleophilicity of the polymerization catalyst and duration of the postcure. The isocyanate and epoxide polymerization mechanism in the presence of nucleophiles is also investigated to explain the effect of the catalyst nucleophilicity on the chemical composition as well as the healing performance of the ISOX polymers.

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Oxazolidine | C3H1200NO – PubChem

 

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Aza-Michael reactions of enones with carbamates took efficiently in the presence of a catalytic amount of quaternary ammonium salts and BF 3·OEt2 to afford the total products in high yields. The new catalytic system was also efficient in the aza-Michael reaction of chalcone, which was difficult to react with carbamates by transition metal salts catalysts.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1152NO – 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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A novel class of cyclic phosphine derived bifunctional catalysts (Le-Phos) is reported, which can be readily prepared from inexpensive and commercially available starting materials and exhibit good performances in enantioselective gamma-addition reactions of N-centered nucleophiles and allenoates under mild conditions. The salient features of this reaction include high product yields, good enantioselectivity, mild reaction conditions, and broad substrate scope and gram-scale scalability.

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The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious S-nitrosoglutathione reductase (GSNOR) inhibitor and is currently undergoing clinical development for the treatment of acute asthma. GSNOR is a member of the alcohol dehydrogenase family (ADH) and regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). Reduced levels of GSNO, as well as other nitrosothiols (SNOs), have been implicated in the pathogenesis of many diseases including those of the respiratory, cardiovascular, and gastrointestinal systems. Preservation of endogenous SNOs through GSNOR inhibition presents a novel therapeutic approach with broad applicability. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogues of N6022 focusing on removal of cytochrome P450 inhibition activities. We identified potent and novel GSNOR inhibitors having reduced CYP inhibition activities and demonstrated efficacy in a mouse ovalbumin (OVA) model of asthma.

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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); wherein A is -C(R1)= or -N=; and X is selected from the group consisting of: (II-i), and (II-ii). 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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A four-step route to the tetracyclic ring system found in a number of indole alkaloids is described using stereoselective dipolar cycloaddition reactions of azomethine ylides. The ylides were derived from N-protected 2-butenylindole-3-carbaldehydes, which were prepared in three steps from 2-methylindole. Condensation of these aldehydes with a variety of alkylamino esters or amino acids or with N-methylhydroxylamine gave the required azomethine ylides or nitrone that undergo intramolecular cycloaddition onto the pendant, unactivated alkene. The cycloaddition sets up two new rings and up to three new stereocentres stereoselectively. After cycloaddition with N-allylglycine, N-deallylation provided the N-unsubstituted product and this constitutes a formal synthesis of the alkaloid deethylibophyllidine. The cycloaddition chemistry was also shown to be amenable as a route to the alkaloid ibophyllidine or epiibophyllidine, although the use of 2-(allylamino)butyric acid to prepare the azomethine ylide can favour competing iminium ion isomerisation and hydrolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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Oxazolidine – Wikipedia,
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A concise, one-pot route to oxazoles and furocoumarins has been reported. The key step in this transformation involves in situ generation of N-acyliminium ion (NAI) precursor under catalyst and solvent-free conditions and their further transformations promoted by superacid in the same pot. We have also presented the experimental evidence for the involvement of proto-solvated novel exocyclic N-acyliminium ion. Further, the UV-visible and fluorescence studies revealed that few of the compounds reported here exhibited emission of blue light upon irradiation in EtOH in the region of 404-422 nm.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H324NO – PubChem

 

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A highly regioselective method to access 5-amido fully substituted 1,2,3-triazoles by iridium-catalyzed azide-ynamide cycloaddition under mild, air, aqueous, and bioorthogonal conditions is reported. The excellent regioselectivities may derive from the strong coordination between the carbonyl oxygen of ynamide and the -acidic iridium. Since the iridium ion is insensitive to oxygen/water and exhibits low cytotoxicity, it could catalyze this reaction in both organic and biological environments efficiently. Preparation in gram-scale and application in carbohydrates highlight this method.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1016NO – PubChem