A convergent strategy for the synthesis of multisubstituted
pyridines
is described. Vinylallenes combine with commercially available arylsulfonyl
cyanides in Diels–Alder cycloadditions to generate isopyridine
cycloadducts that are converted to pyridines upon further heating
or addition of a base. The 2-sulfonylpyridine products undergo nucleophilic
aromatic substitution reactions with oxygen and carbon nucleophiles
to provide access to a variety of highly substituted pyridines.
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