Herein, we report
a facile isocoumarin and isoquinolone
preparation
by taking advantage of an initial bis(triflyl)ethylation [triflyl
= (trifluoromethyl)sulfonyl] reaction, followed by heterocyclization,
which contrasts with our previous results on cyclobutene formation.
The efficiency of the catalyst- and irradiation-free heterocyclization/bis(triflyl)ethylation
sequence showed exquisite dependence on the electronic nature of the
substituents at the 2-ethynylbenzoate(benzamide) precursors. Molecular
docking of model bis(triflyl)ethylated isocoumarins on human acetylcholinesterase
(hAChE) revealed promising biological activities through selective
coordination on both the catalytic active site and peripheral active
site.