59019-41-9Relevant academic research and scientific papers
Dehydration of isoxazoline N-oxides under electrophilic conditions – an alternative approach toward 3-haloisoxazoles
Fadeeva, Anastasia A.,Ioffe, Sema L.,Tabolin, Andrey A.
supporting information, (2021/05/06)
A new method was developed for the synthesis of fully substituted 3-haloisoxazoles. This process includes the synthesis of isoxazoline N-oxides from α-halonitroalkenes and subsequent dehydration mediated by the silyl triflate/triethylamine system.
Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes - Functionalized Fluorinated Building Blocks for Organic Synthesis
Motornov, Vladimir A.,Muzalevskiy, Vasiliy M.,Tabolin, Andrey A.,Novikov, Roman A.,Nelyubina, Yulia V.,Nenajdenko, Valentine G.,Ioffe, Sema L.
, p. 5274 - 5284 (2017/05/24)
A new highly efficient method for the synthesis of 2-fluoro-2-nitrostyrenes was described. Radical nitration of readily available 2-bromo-2-fluorostyrenes with Fe(NO3)3·9H2O resulted in the formation of the corresponding α-fluoro-nitroalkenes in isolated yields up to 92%. The reaction proceeded as a nitration-debromination sequence to highly stereoselectively give α-fluoro-nitroalkenes as Z-isomers only. The broad scope of this method was demonstrated. Prepared monofluorinated alkenes were shown to be versatile building blocks for the synthesis of various fluorinated products.
Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes
Ganesh, Madhu,Namboothiri, Irishi N.N.
, p. 11973 - 11983 (2008/03/13)
(Z)-α-Bromo-β-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)4 as catalyst to afford (E)-α,β-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of α-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful α,β-disubstituted nitroethylenes.
Reactions of 1-Bromo-2-(p-chlorophenyl)-1-nitroethene with CH Acids
Trukhin,Makarenko,Berestovitskaya
, p. 59 - 67 (2007/10/03)
According to 1H NMR and UV spectral data, 1-bromo-2-(p-chlorophenyl)-1-nitroethene has Z configuration. Its reactions with a series of CH acids result in formation of nucleophilic addition products (with 2-phenyl-1,3-indandione and diethyl malo
Research on antitumor chemotherapy: X. β Nitrostyrene and nitrovinyl derivatives
Dore,Viel
, p. 81 - 109 (2007/10/06)
In previous work, the antitumoral cytotoxicity of β nitrostyrenes obtained by simplification of the aristolochic acid molecule was demonstrated. The effect of modifying the 3 characteristic parts of the β nitrostyrene molecule was then investigated. Results in vitro and in vivo indicate a probable mechanism of action for the β nitrostyrene and nitrovinyl compounds studied, and permit definition of the maximum simplification compatible with retention of biological activity.
