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一条从甲基取代杂环和胺出发,可持续的无金属、无添加剂的制备β-杂氮芳烃的烯烃化路线。

A sustainable metal-free and additive-free olefination route to -heteroazaarenes from methyl-substituted heterocycles and amines.

作者信息

Cui Hongyi, Zhang Chunyan, Ji Yuqi, Zhang Guoying

机构信息

State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences Taiyuan 030001 P. R. China

University of Chinese Academy of Sciences Beijing 100049 China.

出版信息

RSC Adv. 2024 Jan 31;14(7):4339-4344. doi: 10.1039/d4ra00189c.

DOI:10.1039/d4ra00189c
PMID:38304557
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10828934/
Abstract

A green and sustainable metal-free, additive-free olefination approach is proposed for the facile synthesis of various unsaturated -heteroazaarenes from simple methyl-substituted heteroarenes and amines. The developed protocol employs only air as the sole oxidant and provides a useful strategy for obtaining various -selective conjugated heterocyclic olefins. This provides a useful strategy for application in generating grams of a variety of unsaturated -heteroazaarenes (up to 20.33 grams) and the synthetic imaging agents of STB-8 (2.40 gram) with high regioselectivity in one pot.

摘要

提出了一种绿色可持续的无金属、无添加剂的烯化方法,用于从简单的甲基取代杂芳烃和胺轻松合成各种不饱和杂氮芳烃。所开发的方案仅使用空气作为唯一的氧化剂,并为获得各种区域选择性共轭杂环烯烃提供了一种有用的策略。这为一锅法制备克级的各种不饱和杂氮芳烃(高达20.33克)和具有高区域选择性的STB-8合成成像剂(2.40克)提供了一种有用的策略。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/10828934/6763650053df/d4ra00189c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/10828934/ef301eb5797c/d4ra00189c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/10828934/53a3b3d6916a/d4ra00189c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/10828934/13d047b52c3f/d4ra00189c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/10828934/6763650053df/d4ra00189c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/10828934/ef301eb5797c/d4ra00189c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/10828934/53a3b3d6916a/d4ra00189c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/10828934/13d047b52c3f/d4ra00189c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d71/10828934/6763650053df/d4ra00189c-f1.jpg

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Deaminative Olefination of Methyl -Heteroarenes by an Amine Oxidase Inspired Catalyst.胺氧化酶模拟催化剂促进的甲基杂环芳烃的脱氨烯烃化反应
Org Lett. 2021 Jan 15;23(2):542-547. doi: 10.1021/acs.orglett.0c04060. Epub 2021 Jan 7.
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NaCl as Catalyst and Water as Solvent: Highly -Selective Olefination of Methyl Substituted -Heteroarenes with Benzyl Amines and Alcohols.
以氯化钠为催化剂、水为溶剂:甲基取代杂芳烃与苄胺及醇的高选择性烯化反应
Org Lett. 2020 Jul 17;22(14):5496-5501. doi: 10.1021/acs.orglett.0c01851. Epub 2020 Jun 30.
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Montelukast Prevents Mice Against Acetaminophen-Induced Liver Injury.孟鲁司特可预防小鼠对乙酰氨基酚诱导的肝损伤。
Front Pharmacol. 2019 Sep 18;10:1070. doi: 10.3389/fphar.2019.01070. eCollection 2019.
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