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An eccentric rod-like linear connection of two heterocycles: synthesis of pyridine trans-tetrafluoro-?6-sulfanyl triazoles.

ABSTRACT: The trans-tetrafluoro-?6-sulfane (SF4) 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 SF4-alkynes and readily available azides, providing a series of rod-like SF4-connected N-heterocycles in good to excellent yields. X-ray crystallographic analysis of the target products revealed the trans-geometry of the SF4 group, which linearly connects two independent N-heterocycles. This research will open the field of chemistry of SF4-connected heterocyclic compounds.

SUBMITTER: Das P

PROVIDER: S-EPMC5994873 | biostudies-other | 2018 Jun

REPOSITORIES: biostudies-other

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An eccentric rod-like linear connection of two heterocycles: synthesis of pyridine trans-tetrafluoro-λ6-sulfanyl triazoles.

Das Prajwalita P Niina Kiyoteru K Hiromura Tomoya T Tokunaga Etsuko E Saito Norimichi N Shibata Norio N

Chemical science 20180514 22

The trans-tetrafluoro-λ6-sulfane (SF4) 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 SF4-alkynes and readily available azides, providing a series of rod-like SF4-connected N-heterocycles in good t ...[more]

PMID: 29938019

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