Effect of the leaving group on the reaction of 2-aminopyrroles with electron deficient heteroaromatic azadienes: substitution by addition–elimination versus cycloaddition
- 作者：Michael De Rosa ; David Arnold ; Miroslav Medved’
- 关键词：2-Aminopyrroles ; Substitution ; Addition– ; elimination ; Ambident behaviour ; Zwitterions ; Meisenheimer complex ; Leaving group ; Steric effects
- 刊名：Tetrahedron Letters
- 出版年：2007
- 期刊代码：109_00404039
- 类别：ch
- 出版时间：4 June 2007
- 卷：48
- 期：23
- 页码：3991-3994
- 文件大小：126 K
摘要
When a good leaving group is present in the heteroaromatic azadiene, reaction with 2-aminopyrroles occurs by substitution by addition–elimination instead of cycloaddition. This novel reaction is sensitive to steric effects and takes place in 2-amino-1-methylpyrrole at C-5 and the exo amino group but at C-3 in 2-amino-1-t-butylpyrrole.