The synthesis of nucleoside analogues from nitroimidazole precursors.
An introduction to nucleoside analogues containing heterocyclic sugar
mimics and their synthesis is presented. This includes various ring sizes and
different heteroatom combinations. concentrated on work between 1995-2000.
The synthesis of novel nucleoside analogues from nitroimidazole precursors
has been investigated.
The regioisorners I-vinyl-4-nitroimidazole and I-vinyl-S-nitroimidazole
have been synthesised from the readily available 4/S-nitroimidazole. Also
synthesised from 4/S-nitroimidazoIe IS 3-vinyl-imidazo[ 4' ,S' :S,6]pyrido[2,3-
d]pyrimidin-8-one, the pyridine stretched analogue of 3-vinylinosine. 1,3-Dipolar
cycloaddition reactions of these three molecules are studied, with stabilised and
unstabilised 1,3-dipolar compounds. to produce heterocyclic nucleoside analogues.
Structures of these cycloadducts are investigated using nrnr studies to determine the
regiochemistry of the reactions. This nrnr evidence is supported my MO
Further studies have established synthetic routes to the pyridine stretched
analogues of 2'-deoxyadenosine and 2'-deoxyinosine from deoxyribose and 4/5-
nitroimidazole, involving directing the coupling of a chlorosugar to the sodium salt
of 4-nitroimidazoIe to yield a maximum of the S-nitroimidazole isomer product