Abstract
A new and straightforward methodology is described for the construction of complex nitrogen-containing polycycles from substituted 1,2,4-triazines and enamines, prepared in situ from carbonyl components and allylic amines. The transformation proceeds via a pericyclic reaction cascade (inverse electron demand Diels-Alder then retro Diels-Alder then intramolecular Diels-Alder) forming the polycyclic systems in good to excellent yield and with high diastereoselectivity in a one-pot procedure. The scope and limitations of the methodology are discribed as are preliminary studies to extend its synthetic utilitiy.
Original language | English |
---|---|
Pages (from-to) | 6004-6014 |
Number of pages | 11 |
Journal | Tetrahedron |
Volume | 63 |
Issue number | 26 |
Early online date | 20 Feb 2007 |
DOIs | |
Publication status | Published - 25 Jun 2007 |
Keywords
- substituted 1,2,4-triazines
- Diels-Alder reactions
- inverse electron demand
- IMDA
- cascade or tandem processes
- diaza-polycycles