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由2-苯乙烯基苯胺和2-甲基苯并噻唑/2-甲基喹啉无金属合成功能化喹啉

Metal-Free Synthesis of Functionalized Quinolines from 2-Styrylanilines and 2-Methylbenzothiazoles/2-Methylquinolines.

作者信息

Liu Xiaoying, Chu Xianglong

机构信息

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

出版信息

ACS Omega. 2023 Feb 13;8(7):6940-6944. doi: 10.1021/acsomega.2c07736. eCollection 2023 Feb 21.

DOI:10.1021/acsomega.2c07736
PMID:36844512
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9948197/
Abstract

A facile functionalization of C(sp)-H bonds and tandem cyclization strategy to synthesize quinoline derivatives from 2-methylbenzothiazoles or 2-methylquinolines and 2-styrylanilines has been developed. This work avoids the requirement for transition metals, offering a mild approach to activation of C(sp)-H bonds and formation of new C-C and C-N bonds. This strategy features excellent functional group tolerance and scaled-up synthetic capability, thus providing an efficient and environmentally friendly access to medicinally valuable quinolines.

摘要

已开发出一种从2-甲基苯并噻唑或2-甲基喹啉与2-苯乙烯基苯胺合成喹啉衍生物的C(sp)-H键简便官能团化及串联环化策略。这项工作避免了对过渡金属的需求，提供了一种温和的方法来活化C(sp)-H键并形成新的C-C和C-N键。该策略具有出色的官能团耐受性和放大合成能力，从而为具有药用价值的喹啉提供了一种高效且环保的合成途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/a74f29df8733/ao2c07736_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/cb160d7c10ae/ao2c07736_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/761099ac1917/ao2c07736_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/52b9c8eedcc2/ao2c07736_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/00e3d9ef55d1/ao2c07736_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/741a1305c71a/ao2c07736_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/bc67c1a9331e/ao2c07736_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/a74f29df8733/ao2c07736_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/cb160d7c10ae/ao2c07736_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/761099ac1917/ao2c07736_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/52b9c8eedcc2/ao2c07736_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/00e3d9ef55d1/ao2c07736_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/741a1305c71a/ao2c07736_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/bc67c1a9331e/ao2c07736_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c2ee/9948197/a74f29df8733/ao2c07736_0008.jpg

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本文引用的文献

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Nat Rev Chem. 2022 Jun;6(6):405-427. doi: 10.1038/s41570-022-00388-4. Epub 2022 May 17.
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Recent advances in chemistry and therapeutic potential of functionalized quinoline motifs - a review.功能化喹啉基序的化学进展与治疗潜力——综述
RSC Adv. 2022 Jun 24;12(29):18594-18614. doi: 10.1039/d2ra02896d. eCollection 2022 Jun 22.
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Prescribed drugs containing nitrogen heterocycles: an overview.含氮杂环的处方药：概述
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