The
reactivity of readily available 4,5-fused-1-sulfonyl-1,2,3-triazoles
was examined in the Rh(II)-catalyzed transannulation reaction with
nitriles. We have come across the interesting observation that 1-sulfonyl
cycloalkeno[d][1,2,3]triazoles that possess β-hydrogens
resist intramolecular β-hydride migration and could serve as
a new source of Rh-iminocarbenoids for intermolecular Rh(II)-catalyzed
transannulation reactions. As a result, 1-sulfonyl cyclohexeno-, cyclohepteno-,
dihydropyrano-, 5-phenyltetrahydrobenzo-, and 4,5-dihydronaphtho[d]imidazoles were synthesized from various nitriles in good
yields. A one-pot methodology has also been executed for the synthesis
of NH-imidazoles.
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