Diverse trifluoromethyl-substituted
compounds were synthesized
by deoxofluorination of cinnamic and (hetero)aromatic carboxylic acids
with sulfur tetrafluoride. The obtained products were used as starting
materials in the preparation of novel fluorinated amino acids, anilines,
and aliphatic amines - valuable building blocks for medicinal chemistry
and agrochemistry.
An efficient chlorotrimethylsilane-promoted
synthetic protocol
for the preparation of functionalized fused β-trifluoromethyl
pyridines by cyclization of electron-rich aminoheterocycles or substituted
anilines with a trifluoromethyl vinamidinium salt was developed. The
efficient and scalable approach for producing represented trifluoromethyl
vinamidinium salt demonstrated huge prospects for further use. The
structure specificities of the trifluoromethyl vinamidinium salt and
their impact on the reaction progress were determined. The procedure’s
scope and alternative ways of the reaction were investigated. The
possibility of increasing the reaction scale up to 50 g and further
modification of obtained products was shown. A minilibrary of potential
fragments for 19F NMR-based fragment-based drug discovery
(FBDD) was synthesized.
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