Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences

one-pot synthesis of diaza-polycycles

William Bromley, Mairi Gibson, Stuart Lang, Steven Raw, Adrian Whitwood, Richard Taylor

Research output: Contribution to journalArticle

29 Citations (Scopus)

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 languageEnglish
Pages (from-to)6004-6014
Number of pages11
JournalTetrahedron
Volume63
Issue number26
Early online date20 Feb 2007
DOIs
Publication statusPublished - 25 Jun 2007

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Amines
Nitrogen
Electrons
1,2,4-triazine

Keywords

  • substituted 1,2,4-triazines
  • Diels-Alder reactions
  • inverse electron demand
  • IMDA
  • cascade or tandem processes
  • diaza-polycycles

Cite this

Bromley, William ; Gibson, Mairi ; Lang, Stuart ; Raw, Steven ; Whitwood, Adrian ; Taylor, Richard. / Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences : one-pot synthesis of diaza-polycycles. In: Tetrahedron. 2007 ; Vol. 63, No. 26. pp. 6004-6014.
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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.",
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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 journalArticle

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

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SP - 6004

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JO - Tetrahedron

JF - Tetrahedron

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