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
收藏
页码：1865 / 1869
页数：5
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