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喹啉的合成:顺序加成和碘介导的脱硫环化反应。

Synthesis of quinolines sequential addition and I-mediated desulfurative cyclization.

作者信息

Yang Mingming, Jian Yajun, Zhang Weiqiang, Sun Huaming, Zhang Guofang, Wang Yanyan, Gao Ziwei

机构信息

Key Laboratory of Applied Surface and Colloid Chemistry, Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University Xi'an 710119 P. R. China

A School of Chemistry & Chemical Engineering, Xinjiang Normal University Urumqi 830054 P. R. China.

出版信息

RSC Adv. 2021 Dec 6;11(61):38889-38893. doi: 10.1039/d1ra06976d. eCollection 2021 Nov 29.

DOI:10.1039/d1ra06976d
PMID:35493239
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9044151/
Abstract

An efficient one-pot approach for the synthesis of quinolines from -aminothiophenol and 1,3-ynone under mild conditions is disclosed. With the aid of ESI-MS analysis and parallel experiments, a three-step mechanism is proposed-a two-step Michael addition-cyclization condensation step leading to intermediate 1,5-benzothiazepine catalyzed by zirconocene amino acid complex CpZr(η-CHNO), followed by I-mediated desulfurative step.

摘要

公开了一种在温和条件下由β-氨基苯硫酚和1,3-烯炔酮高效一锅法合成喹啉的方法。借助电喷雾电离质谱(ESI-MS)分析和平行实验,提出了一种三步机理——由二茂锆氨基酸络合物CpZr(η⁵-CHNO)催化的两步迈克尔加成-环化缩合步骤,生成中间体1,5-苯并硫氮杂䓬,随后是碘介导的脱硫步骤。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d6/9044151/c66fc8f346cb/d1ra06976d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d6/9044151/822cbcafb9b2/d1ra06976d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d6/9044151/c66fc8f346cb/d1ra06976d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d6/9044151/822cbcafb9b2/d1ra06976d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e7d6/9044151/c66fc8f346cb/d1ra06976d-s2.jpg

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Recent advances in the synthesis of biologically and pharmaceutically active quinoline and its analogues: a review.生物及药用活性喹啉及其类似物合成的最新进展:综述
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Synthetic- and DFT modelling studies on regioselective modified Mannich reactions of hydroxy-KYNA derivatives.
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Gram-Scale Synthesis of 1,8-Naphthyridines in Water: The Friedlander Reaction Revisited.水中1,8-萘啶的克级合成:对Friedlander反应的重新审视
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