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6-色烯并[4,3 -]喹啉-6-酮的有氧无金属合成

Aerobic, metal-free synthesis of 6-chromeno[4,3-]quinolin-6-ones.

作者信息

Ton Nhan N H, Dang Ha V, Phan Nam T S, Nguyen Tung T

机构信息

Faculty of Chemical Engineering, HCMC University of Technology, VNU-HCM 268 Ly Thuong Kiet, District 10 Ho Chi Minh City Vietnam

出版信息

RSC Adv. 2019 May 23;9(28):16215-16222. doi: 10.1039/c9ra02267h. eCollection 2019 May 20.

DOI:10.1039/c9ra02267h
PMID:35521415
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9064357/
Abstract

A Friedländer-based method for transition-metal free, aerobic synthesis of chromene-fused quinolinones is reported. The coupling of 4-hydrocoumarins and 2-aminobenzyl alcohols proceeds in the presence of acetic acid solvent and oxygen oxidant, affording 6-chromeno[4,3-]quinolin-6-ones in good to excellent yields. The reactions are tolerant of functionalities such as alkyl, methoxy, bromo, chloro, and -heterocycle. Isosteric cyclic 1,3-diketones and 2-amino acetophenones also give fused quinolinones under reaction conditions. The method herein offers a rapid and benign synthesis of hitherto challenging -heterocycles. To our best knowledge, such a convenient pathway to obtain chromene-fused quinolinones have not been known in the literature.

摘要

报道了一种基于Friedländer反应的无过渡金属、有氧合成色烯并喹啉酮的方法。4-氢香豆素与2-氨基苄醇在乙酸溶剂和氧气氧化剂存在下发生偶联反应，以良好至优异的产率得到6-色烯并[4,3 -]喹啉-6-酮。该反应对烷基、甲氧基、溴、氯和杂环等官能团具有耐受性。等排环状1,3 -二酮和2-氨基苯乙酮在反应条件下也能生成稠合喹啉酮。本文所述方法为迄今具有挑战性的杂环提供了一种快速且温和的合成方法。据我们所知，文献中尚未报道过如此便捷的获得色烯并喹啉酮的途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0e0/9064357/7310d2ab88c2/c9ra02267h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0e0/9064357/83047a491f69/c9ra02267h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0e0/9064357/48ab4190ce1b/c9ra02267h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0e0/9064357/7d51409b243e/c9ra02267h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0e0/9064357/7310d2ab88c2/c9ra02267h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0e0/9064357/83047a491f69/c9ra02267h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0e0/9064357/48ab4190ce1b/c9ra02267h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0e0/9064357/7d51409b243e/c9ra02267h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0e0/9064357/7310d2ab88c2/c9ra02267h-s4.jpg

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本文引用的文献

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An unprecedented tandem synthesis of fluorescent coumarin-fused pyrimidines via copper-catalyzed cross-dehydrogenative C(sp)-N bond coupling.通过铜催化的交叉脱氢 C(sp)-N 键偶联反应，实现了前所未有的荧光香豆素融合嘧啶的串联合成。
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A nickel catalyzed acceptorless dehydrogenative approach to quinolines.
镍催化的无受体脱氢喹啉方法。
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Copper-Catalyzed Cyclization for Access to 6H-Chromeno[4,3-b]quinolin-6-ones Employing DMF as the Carbon Source.铜催化环化反应用于构建 6H-色烯并[4,3-b]喹啉-6-酮：DMF 作为碳源的应用。
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Ionic liquid-functionalized magnetic nanostructures as an efficient catalyst for the synthesis of 6H-chromeno[4,3-b]quinolin-6-ones.离子液体功能化磁性纳米结构作为一种高效催化剂，用于合成 6H-色烯并[4,3-b]喹啉-6-酮。
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