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


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.

DOI: 10.1002/asia.201402421

Cite this paper

@article{Zhu2014FormalO, title={Formal [4+2]-annulation of vinyl azides with N-unsaturated aldimines.}, author={Xu Zhu and Yi-Feng Wang and Feng-Lian Zhang and Shunsuke Chiba}, journal={Chemistry, an Asian journal}, year={2014}, volume={9 9}, pages={2458-62} }