Thesis (M.Sc.)-University of Natal, Durban, 1993.Recent work in our laboratory has led to a new synthesis of
the 2-oxo-a8'&-hexahydroquinoline ring system. This involved
the condensation of B-alkylaminopropanoates with
2-methylcyclohexanone. Further reactions of B-aminopropanoates
with other cyclic ketones and acyclic ketones have been
investigated and are now reported. These reactions are found to
be sensitive to steric effects, the stability of the ketone and
the presence of molecular sieves and have led not only to the
synthesis of the quinolone ring system but also to the
inden-7-one and pyridone ring systems.
A new one pot synthesis of the bicyclo[2.2.2]octan-5-one ring
system from acyclic precursors has recently been reported.
Reaction of" two equivalents of phenyl vinyl ketone with one
equivalent of N-2-butylidenebenzylamine has lead to the
synthesis of 2-benzoyl-4-methyl-l-phenylbicyclo[2.2.2]octan-5one
as a mixture of two isomers. This reaction has now been
extended to N-2-(4-phenylbutylidene)propylamine and
ethyl N-propyl-4-iminopentanoate and our findings are reported
