Mechanism of the inverse-electron demand Diels–Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid
- 作者：Michael De Rosa ; David Arnold
- 关键词：2-Aminopyrroles ; Inverse-electron demand Diels– ; Alder ; Zwitterion intermediate ; Meisenheimer complex ; Cascade mechanism
- 刊名：Tetrahedron Letters
- 出版年：2007
- 期刊代码：109_00404039
- 类别：ch
- 出版时间：23 April 2007
- 卷：48
- 期：17
- 页码：2975-2977
- 文件大小：231 K
摘要
In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur.