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

Keywords

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

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