Thesis-2005-Pillainayagam.pdf (3.67 MB)

New methods in tetramic acid synthesis

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thesis
posted on 05.10.2018, 09:54 by Terence A. Pillainayagam
The work carried out during this PhD programme has been concerned with the reinvestigation and development of a general synthetic methodology towards the 3- acyltetramic acids (3-acylpyrrolidine-2,4-diones). Through a nitrile oxide cycloaddition strategy developed previously within our group we have synthesised a variety of 'masked' isoxazole precursors. We have further developed this strategy to include extension at the C-3 position in the bicyclic 3-methylpyrrolo[3,4-c]isoxazoles by deprotonation and condensation with a variety of aromatic aldehydes. Ring opening of the products with hydrogen yielded novel 3-(3-arylpropanoyl)tetramic acids, whilst using molybdenum hexacarbonyl produced 3-(3-arylpropenoyl)tetramic acids. Extension of the C-3 position on the 3-methylpyrrolo[3,4-c]isoxazoles has also been accomplished using aliphatic ketones.

History

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  • Science

Department

  • Chemistry

Publisher

© T.A. Pillainayagam

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This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2005

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.

Language

en

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