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Issue 22, 2018
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An eccentric rod-like linear connection of two heterocycles: synthesis of pyridine trans-tetrafluoro-λ6-sulfanyl triazoles

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Abstract

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 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.

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

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Publication details

The article was received on 14 Mar 2018, accepted on 12 May 2018 and first published on 14 May 2018


Article type: Edge Article
DOI: 10.1039/C8SC01216D
Citation: Chem. Sci., 2018,9, 4931-4936
  • Open access: Creative Commons BY license
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    An eccentric rod-like linear connection of two heterocycles: synthesis of pyridine trans-tetrafluoro-λ6-sulfanyl triazoles

    P. Das, K. Niina, T. Hiromura, E. Tokunaga, N. Saito and N. Shibata, Chem. Sci., 2018, 9, 4931
    DOI: 10.1039/C8SC01216D

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