15806-71-0Relevant academic research and scientific papers
Metal-free enaminone C-N bond cyanation for the stereoselective synthesis of (E)- And (Z)-β-cyano enones
Liu, Ting,Liu, Yunyun,Wan, Jie-Ping
supporting information, p. 9112 - 9115 (2021/09/14)
A highly practical method for C-CN bond formation by C-N bond cleavage on enaminones leading to the efficient synthesis of β-cyano enones is developed. The reactions take place efficiently to provide (E)-β-cyano enones with only a molecular iodine catalyst. In addition, the additional employment of oxalic acid enables the selective synthesis of (Z)-β-cyano enones.
Catalytic Hydrocyanation of Activated Terminal Alkynes
Tejedor, David,Delgado-Hernández, Samuel,Colella, Lucía,García-Tellado, Fernando
supporting information, p. 15046 - 15049 (2019/11/22)
A universal, practical and scalable organocatalytic hydrocyanation manifold to provide β-substituted acrylonitriles bearing an electron-withdrawing functionality has been implemented. The catalytic manifold operates under the reactivity generation principle “a good nucleophile generates a strong base”, and it uses 1,4-diazabicyclo[2.2.2]octane (DABCO) as the catalyst, activated terminal alkynes as substrates and acetone cyanohydrin as the cyanide source. The acrylonitriles obtained as E,Z mixtures are straightforwardly resolved by simple flash chromatography delivering the pure isomers in preparative amounts.
Metal free electrophilic fluoro-cyclization of unsaturated N-hydroxy- and N-acetoxyamides with N-F reagents
Lourie, Lyudmila F.,Serguchev, Yurii A.,Bentya, Anton V.,Ponomarenko, Maxim V.,Rusanov, Eduard B.,Vovk, Michail V.,Fokin, Andrey A.,Ignat'ev, Nikolai V.
, p. 42 - 47 (2015/11/10)
Metal-free electrophilic fluoro-cyclizations of the respective unsaturated N-hydroxy- and N-acetoxy-amides under action of the 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2 2 2]octane bis(tetrafluoroborate) (F-TEDA-BF4; trade name Selectfluor)
New preparation of (Z)-1-phenyl-3-cyano-2-propen-1-ones
Trabulsi, Houssam,Rousseau, Gerard
experimental part, p. 2123 - 2134 (2011/07/09)
Reaction of γ-phenyl-β,γ-unsaturated hydroxamates with bis(collidine)-bromine(I) hexafluorophosphate led to the formation of cyclic bromo imidates. Reaction of these with triethylamine led to the formation of 3-cyano-2-propen-1-ones with good yields by a
Preparation of imino lactones by electrophilic cyclization of β,γ-unsaturated hydroxamates: Formation of 3-cyanoprop-2-en-1-ones through fragmentation reactions
Trabulsi, Houssam,Guillot, Regis,Rousseau, Gerard
experimental part, p. 5884 - 5896 (2011/01/04)
Treatment of γ-disubstituted β,γ-unsaturated hydroxamates with bis(collidine)bromine(I) hexafluorophosphate led mainly to the formation of cyclic bromo imidates - the thermodynamic products. Unsaturated cyclic imidates were then obtained by treatment with
