循环级联通过N-阿米基基向高度功能化的异环基架进行循环级联
Noelia Fuentes1, Wangqing Kong, Luis Fernández-Sánchez
1Department of Chemistry, University of Zürich , Winterthurerstrasse 190, 8057 Zürich, Switzerland.
Journal of the American Chemical Society
|January 7, 2015
概括
这项研究展示了新型的激素级联反应,使用N-(arylsulfonyl) acrylamides合成复杂的异环环. 这些方法有效地形成多重键,使得分子复杂性的快速构建成为可能.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 激进的反应 激进的反应
背景情况:
- 氨基基中间体是循环化/基迁移/脱硫化级联中的关键.
- 甲烯胺作为多功能的前体,用于激进的转化.
研究的目的:
- 为了证明基中间体在C-C和C-X键形成中的合成实用性.
- 开发高效的单方法来合成复杂的异环化合物.
- 阐明涉及N--烯烯胺的激素级联反应的机制.
主要方法:
- 激素级联反应是通过添加N- ((arylsulfonyl) acrylamides的双键来启动的.
- 通过使用N-[(2-乙烯基) 烯酸烯酸胺,合成印罗[2,1-a]异诺林-6(5H) -one的单合成.
- 银催化激素级联反应与1,3-二碳烯化合物用于二二氨基合成.
- 控制实验以确定关键中间体和反应步骤.
主要成果:
- 区域选择性合成含有CF3-,SCF3-,Ph2(O) P-和N3的印罗[2,1-a]异诺林-6(5H) -one.
- 四个新键 (C-X,C-C,C-N) 的单形成和一个正式的1,4-aryl迁移.
- 通过银催化基级联合成3,3-非替代-2-二二二的合成.
- 两个C-C键和一个C-N键的连续形成与正式的1,4-aryl迁移.
结论:
- 氨基基中间体对于通过随后的C-C和C-X键形成事件来构建分子复杂性非常有价值.
- 新的单基级联反应为密集的功能化异环提供了高效的访问.
- 开发的方法为复杂的分子架构提供了直接和区域选择性的途径.
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