Diversity-based synthesis of nitrogen heterocycles

Austin, Carolyn Ann (2006) Diversity-based synthesis of nitrogen heterocycles. PhD thesis, University of Glasgow.

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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 phenylethylamino group in ketones iv gave racemic azepanes v. [diagram] 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. [diagram].

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Additional Information: Adviser: Richard Hartley
Keywords: Organic chemistry
Date of Award: 2006
Depositing User: Enlighten Team
Unique ID: glathesis:2006-73442
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 14 Jun 2019 08:56
Last Modified: 14 Jun 2019 08:56
URI: http://theses.gla.ac.uk/id/eprint/73442

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