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两个杂环的一种偏心棒状线性连接：吡啶-四氟-λ-硫烷基三唑的合成

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

作者信息

Das Prajwalita, Niina Kiyoteru, Hiromura Tomoya, Tokunaga Etsuko, Saito Norimichi, Shibata Norio

机构信息

Department of Nanopharmaceutical Sciences and Department of Life Science and Applied Chemistry , Nagoya Institute of Technology , Gokiso, Showa-ku , Nagoya 466-8555 , Japan . Email:

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

出版信息

Chem Sci. 2018 May 14;9(22):4931-4936. doi: 10.1039/c8sc01216d. eCollection 2018 Jun 14.

DOI:10.1039/c8sc01216d
PMID:29938019
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5994873/
Abstract

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.

摘要

四氟-λ-硫烷（SF）基团已被用作一种独特的三维结构单元，用于两个独立的N-杂环（吡啶和三唑）的线性连接。通过热Huisgen 1,3-偶极环加成反应，由先前未知的吡啶SF-炔烃与易得的叠氮化物合成了线性连接的杂环化合物，以良好至优异的产率提供了一系列棒状SF连接的N-杂环。目标产物的X射线晶体学分析揭示了SF基团的几何结构，该基团线性连接两个独立的N-杂环。这项研究将开启SF连接的杂环化合物化学领域。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bcb0/5994873/6b3a16c6e69b/c8sc01216d-s6.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bcb0/5994873/7ff62d575213/c8sc01216d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bcb0/5994873/f5445bd07991/c8sc01216d-s1.jpg
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