Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences : one-pot synthesis of diaza-polycycles

Bromley, William and Gibson, Mairi and Lang, Stuart and Raw, Steven and Whitwood, Adrian and Taylor, Richard (2007) Tandem inverse electron demand Diels-Alder, retro Diels-Alder and intramolecular Diels-Alder sequences : one-pot synthesis of diaza-polycycles. Tetrahedron, 63 (26). pp. 6004-6014. ISSN 0040-4020 (https://doi.org/10.1016/j.tet.2007.02.056)

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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• Item metadata

  Item type:	Article
  ID code:	35773
  Dates:	Date Event 25 June 2007 Published 20 February 2007 Published Online
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	15 Nov 2011 11:52
  Last modified:	31 Jan 2025 03:50
  URI:	https://strathprints.strath.ac.uk/id/eprint/35773