- N-Vinyl-2-oxazolidinone: New preparation methods and first uses as a dienophile
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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.
- Gaulon, Catherine,Gizecki, Patricia,Dhal, Robert,Dujardin, Gilles
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- Photoredox Approach to N-Acyl-N′-aryl-N,N′-aminals Using Enamides and Their Conversion to γ-Lactams
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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.
- Koleoso, Olusesan K.,Elsegood, Mark R. J.,Teat, Simon J.,Kimber, Marc C.
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- Ruthenium-catalyzed synthesis of vinylamides at low acetylene pressure
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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.
- Semina, Elena,Tuzina, Pavel,Bienewald, Frank,Hashmi,Schaub, Thomas
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supporting information
p. 5977 - 5980
(2020/06/04)
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- 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
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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.
- Yar, Muhammad,Fritz, Sven P.,Gates, Paul J.,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
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supporting information; experimental part
p. 160 - 166
(2012/02/04)
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- Enamide-benzyne-[2 + 2] cycloaddition: Stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions
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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.
- Feltenberger, John B.,Hayashi, Ryuji,Tang, Yu,Babiash, Eric S.C.,Hsung, Richard P.
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supporting information; experimental part
p. 3666 - 3669
(2011/02/25)
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- 1,3-Dipolar cycloaddition of N-substituted dipolarophiles and nitrones: Highly efficient solvent-free reaction
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(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.
- Thanh, Binh Nguyen,Martel, Arnaud,Dhal, Robert,Dujardin, Gilles
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p. 2621 - 2632
(2008/09/19)
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- Formation of enamides via palladium(II)-catalyzed vinyl transfer from vinyl ethers to nitrogen nucleophiles
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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).
- Brice, Jodie L.,Meerdink, James E.,Stahl, Shannon S.
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p. 1845 - 1848
(2007/10/03)
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- Organic polymers and novel polymerizable compound
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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.
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- New stannyl enamides
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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.
- Naud, Se?bastien,Cintrat, Jean-Christophe
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p. 1391 - 1397
(2007/10/03)
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- Synthesis of N-vinyl-2-oxazolidone: A commercially important intermediate
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An improved synthesis of N-vinyl-2-oxazolidone starting from ethanolamine has been developed.
- Vani,Chida,Srinivasan,Chandrasekharam,Singh
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p. 2043 - 2046
(2007/10/03)
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- Preparation of N-akenylcarbamic esters
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N-Alkenylcarbamic esters of the general formula I STR1 where at least one of the R1 radicals is hydrogen and the second R1 radical is hydrogen or C1 -C4 --alkyl, the R2 radical is an aliphatic, cycloaliphatic, araliphatic or aromatic radical which can be linked to the R3 radical to form a 2- to 10-membered bridge, and the R3 radical is an aliphatic, cycloaliphatic or aromatic radical, from an alkenyl carboxylate of the general formula II STR2 where R1 has the abovementioned meaning, and R4 is hydrogen, an aliphatic, cycloaliphatic or aromatic radical, and a carbamic ester of the general formula III STR3 where the R2 and R3 radicals have the abovementioned meanings, are prepared by reacting the starting compounds in the presence of a base.
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- Process for production of N-vinyl compound
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The present invention provides a process for producing an N-vinyl compound, which comprises subjecting an N-(-alkoxyalkyl) compound to gas phase intramolecular alcohol elimination to convert said compound to an N-vinyl compound directly in one step, wherein a solid oxide containing phosphorus and an alkali metal and/or an alkaline earth metal is used as a catalyst. This process need not use any solvent or any auxiliary raw material and consequently can produce an N-vinyl compound simply and safely without generating any waste material derived from the auxiliary raw material.
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