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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

 

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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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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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Chemical engineers ensure the efficiency and safety of chemical processes, adapt the chemical make-up of products to meet environmental or economic needs, and apply new technologies to improve existing processes. Electric Literature of 102029-44-7. Introducing a new discovery about 102029-44-7, Name is (R)-4-Benzyl-2-oxazolidinone

Figure presented A Cu-catalyzed aerobic oxidative amidation of propiolic acids via decarboxylation under air has been developed. Only carbon dioxide is produced as byproduct in this approach. The use of air as oxidant makes this method more useful and easy to handle.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1867NO – PubChem

 

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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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Reference:
Oxazolidine – Wikipedia,
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An asymmetric aldol strategy has been developed for the synthesis of L- daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O- TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two- step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similary, lactone 32 was converted to N- benzoylristosamide 42 with an overall yield of 18% starting from 12.

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Oxazolidine – Wikipedia,
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What I Wish Everyone Knew About 5-(Chloromethyl)oxazolidin-2-one

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Copper acetylides are readily available and especially convenient reagents for the alkynylation of a broad range of heteronucleophiles. Upon simple activation with molecular oxygen in the presence of suitable ligands and solvents, they readily transfer their alkyne moiety at room temperature, notably yielding a variety of nitrogen- and phosphorus-substituted alkynes. We report in this manuscript an extensive study of the chemoselectivity of this alkynylation based on quantitative 13C NMR analyses. With suitable ligand/solvent combinations, various phosphorus-based nucleophiles can be alkynylated with excellent levels of selectivity, even in the presence of a large excess of a nitrogen-nucleophile. This chemoselective alkynylation could be further extended to an even more challenging selective alkynylation of a nitrogen-nucleophile over another one, further highlighting the synthetic potential of copper acetylides as alkynylating agents that can selectively ?fish? a nucleophile without affecting others.

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Oxazolidine – Wikipedia,
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The synthesis of a new class of peptidomimetics 1a-j, based on a 1,4-benzodiazepine scaffold and on a C-terminal aspartyl aldehyde building block, is described. Compounds 1a-j provided significant inhibitory activity against falcipains 2A and 2B (FP-2A and FP-2B), two cysteine proteases from Plasmodium falciparum.

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Oxazolidine – Wikipedia,
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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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Discovery of (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one

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With the aim to address an undesired cardiac issue observed with our related compound in the recently disclosed novel series of renin inhibitors, further chemical modifications of this series were performed. Extensive structure-activity relationships studies as well as in vivo cardiac studies using the electrophysiology rat model led to the discovery of clinical candidate trans-adamantan-1-ol analogue 56 (DS-8108b) as a potent renin inhibitor with reduced potential cardiac risk. Oral administration of single doses of 3 and 10 mg/kg of 56 in cynomolgus monkeys pre-treated with furosemide led to significant reduction of mean arterial blood pressure for more than 12 h.

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Reference:
Oxazolidine – Wikipedia,
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