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Title: Diversity-Based Synthesis of Nitrogen Heterocycles
Author: Austin, Carolyn A.
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 2006
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Abstract:
Brief investigations were carried out towards the synthesis of 2,4-disubstituted quinolines and 2,6-disubstituted piperidines using titanium alkylidene chemistry, but these were unsuccessful. A route towards the diversity based stereoselective synthesis of 2-substituted azepane derivatives was explored via titanium alkylidene chemistry. Thioacetals i were reacted with low valent titanium(II) species ii to produce titanium(IV) alkylidenes that were reacted with resin-bound esters iii. Cleavage of the resulting enol ethers led to a small library of amino ketones iv, but reductive amination to give azepanes, remained elusive. However, hydrogenation of the a-phenylethylamino group in ketones iv gave racemic azepanes v. Diversity based synthesis of cyclic imines, both 6 and 7 membered, has been carried out using trityl protected amines vi and vii. Alkylidene formation followed by reaction with a range of resin-bound esters iii gave enol ethers. Cleavage and deprotection under mild acidic conditions followed by treatment with base cyclised aminoketone products to cyclic imines viii and ix.
Supervisor: Not available Sponsor: Not available
Qualification Name: University of Glasgow, 2006 Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.484942  DOI: Not available
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