Two new classes of
heteroarene-fused
[1,2,4]thiadiazole and [1,2,4]selenadiazole are synthesized through
the iodine-mediated [3 + 2] oxidative cyclization of 2-aminoheteroarenes
and isothiocyanates/isoselenocyanates. This oxidative [3 + 2] annulation
strategy is highly regiospecific to proceed a selective C–N
bond formation at the endo-nitrogen of 2-aminoheteroarenes followed
by an intramolecular oxidative N–S/N–Se bond formation.
It is the first example of an I2-mediated oxidative nitrogen–selenium
(N–Se) bond formation.
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