Abstract
| 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 |
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Keywords
- substituted 1,2,4-triazines
- Diels-Alder reactions
- inverse electron demand
- IMDA
- cascade or tandem processes
- diaza-polycycles
Cite this
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Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences : one-pot synthesis of diaza-polycycles. / Bromley, William; Gibson, Mairi; Lang, Stuart; Raw, Steven; Whitwood, Adrian; Taylor, Richard.
In: Tetrahedron, Vol. 63, No. 26, 25.06.2007, p. 6004-6014.Research output: Contribution to journal › Article
TY - JOUR
T1 - Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences
T2 - one-pot synthesis of diaza-polycycles
AU - Bromley, William
AU - Gibson, Mairi
AU - Lang, Stuart
AU - Raw, Steven
AU - Whitwood, Adrian
AU - Taylor, Richard
PY - 2007/6/25
Y1 - 2007/6/25
N2 - 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.
AB - 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.
KW - substituted 1,2,4-triazines
KW - Diels-Alder reactions
KW - inverse electron demand
KW - IMDA
KW - cascade or tandem processes
KW - diaza-polycycles
U2 - 10.1016/j.tet.2007.02.056
DO - 10.1016/j.tet.2007.02.056
M3 - Article
VL - 63
SP - 6004
EP - 6014
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 26
ER -