Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines

• Main Authors: Zhu, Xu, Wang, Yi-Feng, Zhang, Feng-Lian, Chiba, Shunsuke
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2014
• Subjects: DRNTU::Science::Physics::Atomic physics
• Online Access: https://hdl.handle.net/10356/105127; http://hdl.handle.net/10220/20689; http://dx.doi.org/10.1002/asia.201402421
• Institution: Nanyang Technological University

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...