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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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 type: Article ID code: 35773 Dates: DateEvent25 June 2007Published20 February 2007Published OnlineSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 15 Nov 2011 11:52 Last modified: 03 Aug 2024 04:40 URI: https://strathprints.strath.ac.uk/id/eprint/35773