Studies on the Regioselective Nucleophilic Aromatic Substitution (SNAr) Reaction of 2-Substituted 3,5-Dichloropyrazines
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- 作者：Stephanie Scales ; Sarah Johnson ; Qiyue Hu ; Quyen-Quyen Do ; Paul Richardson ; Fen Wang ; John Braganza ; Shijian Ren ; Yadong Wan ; Baojiang Zheng ; Darius Faizi ; Indrawan McAlpine
- 刊名：Organic Letters
- 出版年：2013
- 出版时间：May 3, 2013
- 年：2013
- 卷：15
- 期：9
- 页码：2156-2159
- 全文大小：234K
- 年卷期：v.15,no.9(May 3, 2013)
- ISSN：1523-7052
文摘
Differences in regioselectivity were observed during the SNAr reaction of amines with unsymmetrical 3,5-dichloropyrazines. This study revealed that when the 2-position of the pyrazine was occupied with an electron-withdrawing group (EWG), nucleophilic attack occurred preferentially at the 5-position. When the 2-position was substituted with an electron-donating group (EDG), nucleophilic attack occurred preferentially at the 3-position. These results are reported along with a computational rationale for the experimental observations based on the Fukui index at the reacting centers.