posted on 2018-10-05, 09:54authored byTerence 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.
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.