Issue 22, 2018
From the journal:

Chemical Science

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

Prajwalita Das,a   Kiyoteru Niina,a   Tomoya Hiromura,a   Etsuko Tokunaga, ORCID logo a   Norimichi Saitob  and  Norio Shibata ORCID logo *ac  

* Corresponding authors

a Department of Nanopharmaceutical Sciences and Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
E-mail: nozshiba@nitech.ac.jp

b Pharmaceutical Division, Ube Industries, Ltd., Seavans North Bldg, 1-2-1 Shibaura, Minato-ku, Tokyo 105-8449, Japan

c Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, 321004 Jinhua, China

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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Article information

DOI
https://doi.org/10.1039/C8SC01216D
Article type
Edge Article
Submitted
14 Mar 2018
Accepted
12 May 2018
First published
14 May 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 4931-4936

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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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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