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

被引：10

作者：

Kazin, Nikita A. ^{[1
,2
]}

Kvashnin, Yuriy A. ^{[1
]}

Irgashev, Roman A. ^{[1
,2
]}

Dehaen, Wim ^{[3
]}

Rusinov, Gennady L. ^{[1
,2
]}

Charushin, Valery N. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, Ural Div, Postovsky Inst Organ Synth, S Kovalevskoy Str 22, Ekaterinburg 620041, Russia

[2] Ural Fed Univ Named First President Russia BN Yel, Ekaterinburg 620002, Russia

[3] Katholieke Univ Leuven, Dept Chem, B-3001 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 14期

基金：

俄罗斯基础研究基金会;

关键词：

C-H functionalization; Furazano[3,4-b]pyrazines; beta-Nitrostyrenes; Nucleophilic substitution of hydrogen; Metal-free coupling reactions; Direct arylalkenylation; NUCLEOPHILIC-SUBSTITUTION; HYDROGEN; DERIVATIVES; INHIBITORS; DISCOVERY; CHEMISTRY; AGENTS; SAR;

D O I：

10.1016/j.tetlet.2015.02.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 (S-N(H)). The process is initiated by the Michael addition of morpholine at the C=C double bond of beta-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 beta-nitrostyrenes bearing electron-rich substituents on the aromatic ring are involved in arylalkenylation of furazano[3,4-b]pyrazines. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：1865 / 1869

页数：5

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