The preparation of a number of 2-substituted homophthalimides through the
condensation of homophthalic anhydride with different arylalkyl arnines is reported.
The prepared compounds were alkylated at the 4-position to generate 4-mono-,
4,4-disubstituted and 4-spirocyclic homphthalimides, the analogues of which were
reported to have interesting biological activity. Regioselective reduction of the
4-substituted derivatives generated the corresponding carbinolamides. Treating the
carbinolamides with mineral or Lewis acids generated N-acyliminiurn ions, which
were trapped in situ by one of the following: ( 1) aromatic neucleophiles to
generate analogues of the natural product berberine, (2) alkyl chain migration to
generate tetrahydrophenanthridones and functionalised isoquinolones, (3)
cyclopropane ring-opening to generate 4-alkylisoquinolones, (4) addition to double
bond to generate cyclopentaisoquinolones and (5) benzyl or allyl elimination.
The oxidation of 4-monosubstituted homophthalimides with triplet dioxygen in
alkaline media was investigated, and it generated 4-hydroxyhomophthalimides and
isobenzofurancarboxamides. Treating isobenzofurancarboxamides with POCI3
provided a concise route to analogues of the neuroactive naturally-occurring
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.