8 results match your criteria carbamates oxazolidin-2-ones

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Non-precious metal carbamates as catalysts for the aziridine/CO coupling reaction under mild conditions.

Dalton Trans 2021 Apr;50(15):5351-5359

Dipartimento di Chimica e Chimica Industriale, University of Pisa, Via G. Moruzzi 13, I-56124 Pisa, Italy. and CIRCC, via Celso Ulpiani 27, I-70126 Bari, Italy.

The catalytic potential of a large series of easily available metal carbamates (based on thirteen different non-precious metal elements) was explored for the first time in the coupling reaction between 2-aryl-aziridines and carbon dioxide, working under solventless and ambient conditions and using tetraalkylammonium halides as co-catalysts. The straightforward synthesis of novel [NbCl3(O2CNEt2)2], NbCl, and [NbBr3(O2CNEt2)2], NbBr, is reported. The niobium complex NbCl, in combination with NBu4I, emerged as the best catalyst of the overall series to convert aziridines with small N-alkyl substituents into the corresponding 5-aryl-oxazolidin-2-ones. Read More

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The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction: Access to Privileged Chemical Structures and Scope and Limitations of the Method.

J Org Chem 2020 05 5;85(10):6323-6337. Epub 2020 May 5.

Department of Chemistry and Biochemistry, Calvin University, 1726 Knollcrest Circle SE, Grand Rapids, Michigan 49546, United States.

3-Aryl- and 3-heteroaryloxazolidin-2-ones, by virtue of the diverse pharmacologic activities exhibited by them after subtle changes to their appended substituents, are becoming increasingly important and should be considered privileged chemical structures. The iodocyclocarbamation reaction has been extensively used to make many 3alkyl-5-(halomethyl)oxazolidin-2-ones, but the corresponding aromatic congeners have been relatively underexplored. We suggest that racemic 3-aryl- and 3-heteroaryl-5-(iodomethyl)oxazolidin-2-ones, readily prepared by the iodocyclocarbamation reaction of N-allylated aryl or heteroaryl carbamates, may be useful intermediates for the rapid preparation of potential lead compounds with biological activity. Read More

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PhI(OAc)-mediated 1,2-aminohalogenation of alkynes: a general access to (E)-4-(halomethylene)oxazolidin-2-ones.

Org Biomol Chem 2017 May;15(18):3964-3967

State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China.

A new PhI(OAc)-mediated 1,2-aminohalogenation of prop-2-yn-1-yl carbamates and various halogen sources is presented with excellent selectivity and high step-economy. The reaction is general and rapid for the construction of diverse (E)-4-(halomethylene)oxazolidin-2-ones through the generation of the three-membered ring or N-radical followed by intramolecular cyclization. Read More

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Synthesis and in vitro activity of novel 1,2,4-triazolo[4,3-a]pyrimidine oxazolidinone antibacterial agents.

Bioorg Med Chem Lett 2011 May 29;21(10):2887-9. Epub 2011 Mar 29.

Department of Medicinal Chemistry, New Drug Discovery Research, Ranbaxy Laboratories Limited, R&D III, Plot No. 20, Sector-18, Udyog Vihar Industrial Area, Gurgaon 122 001, India.

The synthesis and antibacterial activity of 3-(4-([1,2,4]triazolo[4,3-a]pyrimidin-3-yl)phenyl)oxazolidin-2-ones is reported. Thiocarbonyl derivatives were found to be potent inhibitors of gram-positive pathogens and compound 4l was two to fourfold more potent than Linezolid. Read More

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Ceria nanoparticles as heterogeneous catalyst for CO2 fixation by omega-aminoalcohols.

Chem Commun (Camb) 2010 Jun 21;46(23):4181-3. Epub 2010 Apr 21.

Instituto de Tecnología Química, CSIC-UPV, Universidad Politécnica de Valencia, Av de los Naranjos s/n, 46022, Valencia, Spain.

In contrast to gamma-Al(2)O(3), TiO(2), ZrO(2), MgO and Y(2)O(3), CeO(2) is a reusable catalyst for the reaction of CO(2) with omega-aminoalcohols to form cyclic carbamates; the highest yield (68%) was obtained for the preparation of N-alkyl 1,3-oxazolidin-2-ones from N-alkyl ethanolamines. Read More

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3-Benzyl-1,3-oxazolidin-2-ones as mGluR2 positive allosteric modulators: Hit-to lead and lead optimization.

Bioorg Med Chem Lett 2009 May 14;19(9):2524-9. Epub 2009 Mar 14.

CNS Chemistry, Pfizer Global Research and Development, Eastern Point Road, Groton, CT 06340, USA.

The discovery, synthesis and SAR of a novel series of 3-benzyl-1,3-oxazolidin-2-ones as positive allosteric modulators (PAMs) of mGluR2 is described. Expedient hit-to-lead work on a single HTS hit led to the identification of a ligand-efficient and structurally attractive series of mGluR2 PAMs. Human microsomal clearance and suboptimal physicochemical properties of the initial lead were improved to give potent, metabolically stable and orally available mGluR2 PAMs. Read More

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Modified Mg : Al hydrotalcite in the synthesis of oxazolidin-2-ones.

Org Biomol Chem 2005 Mar 10;3(6):967-9. Epub 2005 Feb 10.

Department of Organic Chemical Technology, Budapest University of Technology and Economics, H-1521, Budapest, Hungary.

The modified Mg : Al (3 : 1) hydrotalcite has been found to be an efficient catalyst in the conversion of carbamates into oxazolidin-2-ones under mild reaction conditions. A wide variety of oxazolidin-2-ones were obtained with excellent chemical yield. Read More

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Ring-closure reactions through intramolecular displacement of the phenylselenonyl group by nitrogen nucleophiles: a new stereospecific synthesis of N-tosyl and N-benzoyl-1,3-oxazolidin-2-ones from beta-hydroxyalkyl phenyl selenides.

Chemistry 2004 Apr;10(7):1752-64

Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, 06123 Perugia, Italy.

A new and convenient method for the stereospecific synthesis of variously substituted 1,3-oxazolidin-2-ones from the easily available beta-hydroxyalkyl phenyl selenides is presented. After transformation into the N-tosyl or N-benzoyl carbamates, the selenides were oxidized to the corresponding selenones. The key step of the process is the ring-closure reaction, which occurs by stereospecific intramolecular nucleophilic substitution of the selenone group by the nitrogen atom of the carbamate. Read More

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