Formal [4+2]‐Annulation of Vinyl Azides with N‐Unsaturated Aldimines |
| |
| Authors: | Xu Zhu Dr. Yi‐Feng Wang Feng‐Lian Zhang Prof. Shunsuke Chiba |
| |
| Affiliation: | Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65)?6791‐1961 |
| |
| Abstract: | Highly functionalized quinolines and pyridines could be synthesized by BF3?OEt2‐mediated reactions of vinyl azides with N‐aryl and N‐alkenyl aldimines, respectively. The reaction mechanism could be characterized as formal [4+2]‐annulation, including unprecedented enamine‐type nucleophilic attack of vinyl azides to aldimines and subsequent nucleophilic cyclization onto the resulting iminodiazonium ion moieties. |
| |
| Keywords: | annulation azides heterocycles Lewis acids |
|
