Direct arylalkenylation of furazano[3, 4-b]pyrazines via a new C–H functionalization protocol. Issue 14 (1st April 2015)

• Record Type: Journal Article
• Authors: Kazin, Nikita A.; Kvashnin, Yuriy A.; Irgashev, Roman A.; Dehaen, Wim; Rusinov, Gennady L.; Charushin, Valery N.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 14(2015)
• Page Start: 1865
• Page End: 1869
• Publication Date: 2015-04-01
• Subjects: C–H functionalization -- Furazano[3, 4-b]pyrazines -- β-Nitrostyrenes -- Nucleophilic substitution of hydrogen -- Metal-free coupling reactions -- Direct arylalkenylation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.02.091
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 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 (SN H ). 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.