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

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 cycloadditio...

Full description

Saved in:
Bibliographic Details
Published in:Chemical science (Cambridge) 2018-06, Vol.9 (22), p.4931-4936
Main Authors: Das, Prajwalita, Kiyoteru Niina, Hiromura, Tomoya, Tokunaga, Etsuko, Saito, Norimichi, Shibata, Norio
Format: Article
Language:English
Subjects:
Alkynes
Crystallography
Cycloaddition
Heterocyclic compounds
Organic chemistry
Pyridines
Triazoles
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc01216d