Direct arylalkenylation of furazano[3,4-b]pyrazines via a new C–H functionalization protocol

[Display omitted] 6-Styryl-5-(het)arylfurazano[3,4-b]pyrazines have been obtained by novel C–H functionalization, which is a particular case of the nucleophilic substitution of hydrogen (SNH). The process is initiated by the Michael addition of morpholine at the CC double bond of β-nitrostyrenes, an...

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Bibliographic Details
Published in:Tetrahedron letters 2015-04, Vol.56 (14), p.1865-1869
Main Authors: Kazin, Nikita A., Kvashnin, Yuriy A., Irgashev, Roman A., Dehaen, Wim, Rusinov, Gennady L., Charushin, Valery N.
Format: Article
Language:English
Subjects:
Aromatic compounds
Bearing
Bonding
C–H functionalization
Direct arylalkenylation
Furazano[3,4-b]pyrazines
Metal-free coupling reactions
Morpholine
Nitrous acid
Nucleophilic substitution of hydrogen
Tetrahedrons
β-Nitrostyrenes
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Summary:[Display omitted] 6-Styryl-5-(het)arylfurazano[3,4-b]pyrazines have been obtained by novel C–H functionalization, which is a particular case of the nucleophilic substitution of hydrogen (SNH). The process is initiated by the Michael addition of morpholine at the CC double bond of β-nitrostyrenes, and the subsequent addition of the generated carbanion to C-6 of 5-(het)arylfurazano[3,4-b]pyrazines, followed by elimination of nitrous acid and morpholine. It has been shown that in this case, only β-nitrostyrenes bearing electron-rich substituents on the aromatic ring are involved in arylalkenylation of furazano[3,4-b]pyrazines.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.02.091