127784-80-9Relevant academic research and scientific papers
Studies on Intramolecular Cycloadditions Involving 3-Oxidopyridinium
Bromidge, Steven M.,Archer, David A.,Sammes, Peter G.
, p. 353 - 359 (2007/10/02)
3-Oxidopyridinium derivatives bearing a pendant pent-4-enyl group at either N-1 or C-2 undergo intramolecular cycloadditions to form tricyclic systems.The chemistry of these cycloadducts has been explored, and that from the 2-substituted series compared to the cycloadduct from the corresponding pyrylium analogue; the nitrogen containing systems exhibit different chemical reactions in which the nucleophilicity of the nitrogen atom dominates.Quaternisation of the nitrogen atom and base treatment leads to opening of the aza-bridge.In contrast to the oxygen containing systems, no skeletal rearrangements (e.g. of the perhydroazulene to decalin type) were observed.
RECENT STUDIES ON 3-OXIDOPYRYLIUM AND ITS DERIVATIVES
Sammes, Peter G.
, p. 109 - 114 (2007/10/02)
A review of recent chemical studies on 3-oxidopyrylium and its derivatives is presented.Methods for generating 3-oxydopyrylium and substituted derivatives are described.These reactive intermediates undergo a variety of intermolecular and intramolecular cycloaddition reactions.The cycloadducts so formed are highly functionalised and can be used as valuable synthetic intermediates.Intramolecular cycloaddition of the appropriately substituted 3-oxidopyrylium opens a simple route to perhydrazulene and the chemistry of these cycloadducts has been explored; the cycloadducts have proved useful as a means for generating the guaiane and valerane classes of sesquiterpenes.Some intramolecular reactions of the related 3-oxidopyridinium systems are also described.
