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

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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.

Author(s):Bromley, William, Gibson, Mairi, Lang, Stuart, Raw, Steven, Whitwood, Adrian and Taylor, Richard
Item type:Article
ID code:35773
Keywords:substituted 1,2,4-triazines, Diels-Alder reactions , inverse electron demand, IMDA, cascade or tandem processes, diaza-polycycles, Chemistry, Biochemistry, Organic Chemistry, Drug Discovery
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 Feb 2020 03:45
URI:https://strathprints.strath.ac.uk/id/eprint/35773
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