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二茂铁基共轭恶唑并氮杂卓/喹啉:多炔偶联及扩环或重排

Ferrocenyl conjugated oxazepines/quinolines: multiyne coupling and ring-expanding or rearrangement.

作者信息

Lei Yu, Bao Li, Hu Qiong, Zhang Ke, Zong Lingli, Hu Yimin

机构信息

College of Chemistry and Materials Science, Anhui Normal University, Wuhu, China.

出版信息

Front Chem. 2024 Jul 31;12:1441539. doi: 10.3389/fchem.2024.1441539. eCollection 2024.

Abstract

Ferrocenyl conjugated oxazepine/quinoline derivatives were presented through the reaction of hexadehydro-Diels-Alder (HDDA) generated arynes with ferrocenyl oxazolines under mild conditions ring-expanding or rearrangement processes. Water molecule participated in this unexpected rearrangement process to produce quinoline skeletons, and DFT calculations supported a ring-expanding and intramolecular hydrogen migration process for the formation of oxazepine derivatives. Two variants of this chemistry, expanded the reactivity between ferrocenyl conjugated substances and arynes, further providing an innovative approach for the synthesis of ferrocene derivatives.

摘要

通过在温和条件下六脱氢狄尔斯-阿尔德(HDDA)生成的芳炔与二茂铁基恶唑啉的反应,呈现出二茂铁基共轭恶唑嗪/喹啉衍生物,该反应涉及扩环或重排过程。水分子参与了这一意外的重排过程以生成喹啉骨架,密度泛函理论(DFT)计算支持了形成恶唑嗪衍生物的扩环和分子内氢迁移过程。这种化学反应的两个变体扩展了二茂铁基共轭物质与芳炔之间的反应活性,进一步为二茂铁衍生物的合成提供了一种创新方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8e8e/11322062/5bac030bcf43/fchem-12-1441539-g001.jpg

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