| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5220572 | Tetrahedron | 2012 | 8 Pages |
The bromination and oxidation of securinine were studied. An interesting and surprising rearrangement was observed during the reaction of securinine with tribromo-isocyanuric acid or 1,3-dibromo-5,5-dimethylhydantoin in methanol, yielding a stereoselective ring contraction norsecurinine derivative. Meanwhile two oxidation rearrangement products were also reported. Some preliminary discussions on the reactivity of securinine were conducted from these rearrangements; it is believed to be induced by alkaline nitrogen atom of the molecule.
Graphical abstractA ring contraction and an oxidation rearrangement of securinine were reported. Especially the six-membered piperidine ring was contracted to five-membered pyrrolidine ring, which could be used as a new method for organic synthesis. Some preliminary discussions on the reactivity of securinine were conducted from these rearrangements.Figure optionsDownload full-size imageDownload as PowerPoint slide
