4271-26-5Relevant academic research and scientific papers
N-Vinyl-2-oxazolidinone: New preparation methods and first uses as a dienophile
Gaulon, Catherine,Gizecki, Patricia,Dhal, Robert,Dujardin, Gilles
, p. 952 - 956 (2002)
N-Vinyloxazolidinone was conveniently prepared in 73% overall yield by an easy two-step procedure based on the dehydroalkoxylation of an intermediate hemiaminal using trimethylsilyl trifluoromethanesulfonate and triethylamine. The good dienophilicity of this enecarbamate was demonstrated in several [4+2] stereo-controlled processes involving activated 1-oxabutadienes under appropriate Lewis-acid catalyzed conditions. In addition, an unexpected amido-alkylation of the title compound is described under mild conditions.
Photoredox Approach to N-Acyl-N′-aryl-N,N′-aminals Using Enamides and Their Conversion to γ-Lactams
Koleoso, Olusesan K.,Elsegood, Mark R. J.,Teat, Simon J.,Kimber, Marc C.
, p. 1003 - 1006 (2018)
A photoredox catalytic approach to synthetically valuable N-acyl-N′-aryl-N,N′-aminals is described. This method uses the addition of a radical precursor to enamides, with subsequent interception of the cationic iminium intermediate with an arylamine. The reaction has been shown to be compatible with electron-rich and electron-deficient arylamines, and moderate to good levels of diastereoselectivity can be attained using a chiral enamide. Furthermore, the N-acyl-N′-aryl-N,N′-aminal reaction products can be readily cyclized, providing a novel synthetic route to valuable γ-lactams.
Ruthenium-catalyzed synthesis of vinylamides at low acetylene pressure
Semina, Elena,Tuzina, Pavel,Bienewald, Frank,Hashmi,Schaub, Thomas
supporting information, p. 5977 - 5980 (2020/06/04)
The reaction of cyclic amides with acetylene under low pressure, using ruthenium-phosphine catalysts, afforded a broad variety ofN-vinylated amides including (azabicyclic) lactams, oxazolidinones, benzoisoxazolones, isoindolinones, quinoxalinones, oxazinanones, cyclic urea derivatives (imidazolidinones), nucleobases (thymine), amino acid anhydrides and thiazolidinone.
Synthesis of N-vinyloxazolidinones and morpholines from amino alcohols and vinylsulfonium salts: Analysis of the outcome's dependence on the N-protecting group by nanospray mass spectrometry
Yar, Muhammad,Fritz, Sven P.,Gates, Paul J.,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
supporting information; experimental part, p. 160 - 166 (2012/02/04)
The effect of the nature of the N-protecting group on 1,2-amino alcohols in annulation reactions with diphenylvinylsulfonium triflate has been investigated. Although tosyl and sulfinamide groups give morpholines in high yields, the use of N-Cbz leads to a high-yielding synthesis of N-vinyloxazolidinones. The reactions were monitored by nanospray MS/MS, which revealed why reactions are successful and the fate of reactive intermediates in the unsuccessful reactions.
Enamide-benzyne-[2 + 2] cycloaddition: Stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions
Feltenberger, John B.,Hayashi, Ryuji,Tang, Yu,Babiash, Eric S.C.,Hsung, Richard P.
supporting information; experimental part, p. 3666 - 3669 (2011/02/25)
Image Presented Benzyne-[2 + 2] cycloadditions with enamides are described. This effort led to the development of a highly stereoselective tandem [2 + 2] cycloaddition-pericyclic ring-opening-intramolecular-N-tethered-[4 + 2] cycloaddition for rapid assembly of nitrogen heterocycles.
1,3-Dipolar cycloaddition of N-substituted dipolarophiles and nitrones: Highly efficient solvent-free reaction
Thanh, Binh Nguyen,Martel, Arnaud,Dhal, Robert,Dujardin, Gilles
, p. 2621 - 2632 (2008/09/19)
(Chemical Equation Presented) New isoxazolidines were synthesized in good to excellent yields by 1,3-dipolar cycloaddition of N-vinylamide dipolarophiles and nitrones. Strikingly, solvent-free conditions gave high conversion and yields, shortened reaction time, and minimized degradation products. N-Vinyloxazolidin-2-one and its analogues used in these cycloaddition reactions were conveniently prepared in excellent yields by a modified version of Buchwald's one-step copper-catalyzed vinylation using vinyl bromide. From the adducts, a two-step access to various unsymmetric aspartate derivatives was also described.
Formation of enamides via palladium(II)-catalyzed vinyl transfer from vinyl ethers to nitrogen nucleophiles
Brice, Jodie L.,Meerdink, James E.,Stahl, Shannon S.
, p. 1845 - 1848 (2007/10/03)
Matrix presented. Palladium(II) complexes catalyze the formation of enamides via the formal cross-coupling reaction between nitrogen nucleophiles and vinyl ethers. These vinyl transfer reactions proceed in good yields with amide, carbamate, and sulfonamide nucleophiles, and the optimal catalyst is (DPP)Pd(OCOCF3)2 (DPP = 4,7-diphenyl-1,10-phenanthroline).
Organic polymers and novel polymerizable compound
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, (2008/06/13)
Organic polymers having water contact angles of 20° or smaller, preferably 7° or smaller and equipped with both high wettability and high transparency. The organic polymers may contain as partial structures polar structures of about 3 debyes or higher in dipole moment and are available especially from polymerization of polymerizable compounds having alkylene(thio)urea structures.
New stannyl enamides
Naud, Se?bastien,Cintrat, Jean-Christophe
, p. 1391 - 1397 (2007/10/03)
New stannyl enamines derived from N-ethynyl oxazolidin-2-ones have been obtained. We describe for the first time the preparation of N-ethynyl oxazolidin-2-ones using trimethylsilylethynyl iodonium triflate. The first results of transmetallation and quenching experiments with prochiral carbonyl derivatives to give β-amino alcohols are also described.
Synthesis of N-vinyl-2-oxazolidone: A commercially important intermediate
Vani,Chida,Srinivasan,Chandrasekharam,Singh
, p. 2043 - 2046 (2007/10/03)
An improved synthesis of N-vinyl-2-oxazolidone starting from ethanolamine has been developed.
