Thesis-2005-Pillainayagam.pdf (3.67 MB)
Download fileNew methods in tetramic acid synthesis
thesis
posted on 05.10.2018, 09:54 authored by Terence A. PillainayagamThe 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
School
- Science
Department
- Chemistry