13811-50-2Relevant academic research and scientific papers
Ruthenium-catalyzed synthesis of vinylamides at low acetylene pressure
Semina, Elena,Tuzina, Pavel,Bienewald, Frank,Hashmi,Schaub, Thomas
, p. 5977 - 5980 (2020)
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.
Phosphine-Catalyzed Vinylation at Low Acetylene Pressure
Bienewald, Frank,Comba, Peter,Hashmi, A. Stephen K.,Menche, Maximilian,Rominger, Frank,Schafer, Ansgar,Schaub, Thomas,Sitte, Nikolai A.,Tuzina, Pavel
, p. 13041 - 13055 (2021/09/18)
The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-n-butylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 °C and typically 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and alcohols were successfully vinylated. Furthermore, the in situ generation of a vinyl phosphonium species can also be utilized in Wittig-type functionalization of aldehydes.
SYNTHESIS OF N-VINYL COMPOUNDS BY REACTING CYLIC NH-COMPOUNDS WITH ACETYLENE IN PRESENCE OF HOMOGENOUS CATALYST
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Page/Page column 17-18; 22, (2021/06/26)
Process to produce N-vinyl compounds by homogeneous catalysis, wherein acetylene is reacted with a cyclic compound comprising a cyclic compound having at least one nitrogen as ring member, bearing a substitutable hydrogen residue (cyclic compound C), in a liquid phase in the presence of a ruthenium complex comprising at least one phosphine as ligand (RuCat).
Preparation of N-alkenylureas
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, (2008/06/13)
A process for preparing N-alkenylureas of the general formula I STR1 where R1 and R2 are hydrogen, C1 - to C40 -alkyl, C2 - to C40 -alkenyl, C3 - to C20 -cycloalkyl, C4 - to C20 -alkylcyc1oalkyl, C4 - to C20 -cycloalkylalkyl, aryl, C7 - to C20 -alkylaryl or C7 - to C20 -aralkyl, or aryl, C7 - to C20 -alkylaryl or C7 - to C20 -aralkyl which are mono- to pentasubstituted by C1 - to C8 -alkyl, C1 - to C8 -alkoxy or halogen, together are a C2 - to C10 -alkylene chain which is unsubstituted or mono- to hexasubstituted by C1 - to C8 -alkyl, and R3 and R4 are hydrogen or C1 - to C8 -alkyl, by reaction of ureas of the general formula II STR2 where R1 and R2 have the abovementioned meanings, with an alkenyl carboxylate of the general formula III STR3 where R3 and R4 have the abovementioned meanings and R5 is hydrogen, C1 - to C40 -alkyl, C3 - to C20 -cycloalkyl, C4 - to C20 -alkylcycloalkyl, aryl, C7 - to C20 -alkylaryl, C7 - to C20 -aralkyl, or aryl or C7 - to C20 -aralkyl which is mono- to trisubstituted by C1 - to C8 -alkyl, at from 0° to 180° C. and from 0.01 to 10 bar, by carrying out the reaction in the presence of a base is described.
