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)

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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.

  • 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:11 Nov 2024 10:00
    URI:https://strathprints.strath.ac.uk/id/eprint/35773
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