An eccentric rod-like linear connection of two heterocycles: synthesis of pyridine -tetrafluoro-λ-sulfanyl triazoles.

The -tetrafluoro-λ-sulfane (SF) group has been utilized as a unique three-dimensional building block for the linear connection of two independent N-heterocycles, pyridines and triazoles. The linearly connected heterocyclic compounds were synthesized by thermal Huisgen 1,3-dipolar cycloaddition between previously unknown pyridine SF-alkynes and readily available azides, providing a series of rod-like SF-connected N-heterocycles in good to excellent yields. X-ray crystallographic analysis of the target products revealed the -geometry of the SF group, which linearly connects two independent N-heterocycles. This research will open the field of chemistry of SF-connected heterocyclic compounds.