New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines
Publication Date
December 11, 2008
Creator
Abstract
In Chapter one a review of the l-aza-Diels-Alder reaction is presented. The hetero Diels-Alder reaction of l-aza-l,3-butadienes with both alkene and alkyne dienophiles has been shown to be an efficient and versatile method for the preparation of a large range of nitrogen-containing six-membered heterocycles. The use of electron-rich 1- azadienes in the normal electron-demand Diels-Alder reaction is primarily examined, followed by a brief look at the synthetic applications of the inverse electron-demand process.
In Chapter two the intermolecular hetero-Diels-Alder cyc1oadditions of 3-siloxy-1aza-1,3-butadienes with electron-deficient dienophiles is presented as an efficient route to tri- and tetra-substituted pyridine core of the thiopeptide antibiotic nosiheptide. A series of alpha, beta-unsaturated oximes and hydrazones were prepared and subsequently shown to participate readily in the hetero-Diels-Alder reaction with dimethyl acetylenedicarboxylate.
In Chapter three, the intramolecular Diels-Alder reaction is presented as a versatile method for the preparation of chromeno[ c ]pyridines. First a series of model systems was prepared and shown to undergo thermally induced intramolecular cyc1oaddition. This methodology was then utilised in the rapid preparation of the penta-substituted pyridine core of the anti tumour antibiotic streptonigrin.
Chapter four contains experimental procedures for all of the work detailed above.
Item Type
ethesis
Thesis Type
PhD
Supervisors
Subjects (LC)
Associated Schools / Departments
School of Chemistry
eprints ID
13092
UoN Repository URI
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