402490-62-4Relevant academic research and scientific papers
Green, Catalyst-Free Reaction of Indoles with β-Fluoro-β-nitrostyrenes in Water
Aldoshin, Alexander S.,Tabolin, Andrey A.,Ioffe, Sema L.,Nenajdenko, Valentine G.
, p. 3816 - 3825 (2018/07/31)
The reaction of 2-fluoro-2-nitrostyrenes with various indoles was investigated. We found that the reaction proceeds as a Michael addition in a highly regioselective manner to form 3-(1-aryl-2-fluoro-2-nitroethyl)-1H-indoles. Thus, a green and catalyst-free synthesis of these compounds was developed using water as a reaction medium. The high effectiveness of this approach was demonstrated through the preparation of target products in up to 92 % isolated yield. Subsequent reduction of the nitro group was investigated. We found that due to the instability of the intermediate α-fluoro amines, the reduction led to non-fluorinated tryptamine derivatives.
New synthetic approach to α-fluoro-β-arylvinyl sulfones and their application in Diels-Alder reactions
Shastin, Aleksey V.,Nenajdenko, Valentine G.,Muzalevskiy, Vasiliy M.,Balenkova, Elizabeth S.,Fr?hlich, Roland,Haufe, Günter
, p. 9725 - 9732 (2008/12/22)
A new pathway towards α-fluoro-β-arylvinyl sulfones was elaborated. The reaction of β-bromo-β-fluorostyrenes with sodium 4-methylphenylsulfinate proceeds with maximum 94:6 stereoselectivity and 72-90% yields. The formed α-fluoro-β-arylvinyl sulfones were
Synthesis and Diels-Alder reactions of α-fluoro- and α-trifluoromethylacrylonitriles
Nenajdenko, Valentine G.,Muzalevskiy, Vasiliy M.,Shastin, Aleksey V.,Balenkova, Elizabeth S.,Haufe, Günter
, p. 818 - 826 (2008/03/14)
A novel synthetic method for the preparation of α-fluoro- and the still unknown α-trifluoromethylacrylonitriles is elaborated. The reaction of α-fluorovinylbromides and α-trifluoromethylvinylbromides with CuCN leads to the title compounds in good to high yields. While the α-fluoroacrylonitriles were isolated as mixture of Z/E-isomers, the α-trifluoromethylacrylonitriles were obtained as pure Z-isomers. The α-trifluoromethylacrylonitriles are shown to be excellent dienophiles for Diels-Alder reactions.
Stereoselective preparation of (E)- and (Z)-α-fluorostilbenes via palladium-catalyzed cross-coupling reaction of high E/Z ratio and (Z)-1-bromo-1-fluoroalkenes
Xu, Jianjun,Burton, Donald J.
, p. 3743 - 3747 (2007/10/03)
A highly stereoselective method to prepare both (E)- and (Z)-α-fluorostilbenes is described. 1-Bromo-1-fluoroalkenes (E/Z ≈ 1:1), a readily available starting material, isomerizes to high E/Z ratios by storage at -20 °C or by photolysis at 254 nm. Stille
Fluorinated resveratrol and pterostilbene
Eddarir, Said,Abdelhadi, Zouanate,Rolando, Christian
, p. 9127 - 9130 (2007/10/03)
A general method for the synthesis of polyhydroxylated stilbene monofluorinated on the central double bond based on the Suzuki reaction between a bromofluoroolefin and a phenylboronic acid is described. Synthesis of fluorinated analogues of resveratrol an
