New methods in tetramic acid synthesis
Terence A. Pillainayagam
2134/35179
https://repository.lboro.ac.uk/articles/thesis/New_methods_in_tetramic_acid_synthesis/9398114
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.
2018-10-05 09:54:29
untagged
Chemical Sciences not elsewhere classified