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通过9-AJ催化的α-炔丙酰苯胺衍生物的串联酰基转移-环化反应简便合成吡咯基4-喹啉酮生物碱喹喏拉克酸

Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer-Cyclization of -Alkynoylaniline Derivatives.

作者信息

Saito Koya, Yoshida Masahito, Uekusa Hidehiro, Doi Takayuki

机构信息

Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.

Department of Chemistry, School of Science, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8551, Japan.

出版信息

ACS Omega. 2017 Aug 9;2(8):4370-4381. doi: 10.1021/acsomega.7b00793. eCollection 2017 Aug 31.

DOI:10.1021/acsomega.7b00793
PMID:31457730
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6641763/
Abstract

The synthesis of pyrrolyl 4-quinolinone alkaloid, quinolactacide, and its analogues was successfully achieved using 9-azajulolidine (9-AJ)-catalyzed tandem acyl transfer-regioselective cyclization of ,-diacyl--alkynoylaniline derivatives. In addition, this organocatalytic reaction was successfully utilized for the synthesis of a variety of 3-acyl-4-quinolinones in moderate-to-good yields. Mechanistic studies, including a time course nuclear magnetic resonance (NMR) experiment, indicated that the 1,4-addition of 9-AJ to an ynone system can be considered to be the rate-determining step in this quinolinone synthesis.

摘要

使用9-氮杂环庚三烯（9-AJ）催化的β,γ-二酰基-α-炔酰基苯胺衍生物的串联酰基转移-区域选择性环化反应，成功实现了吡咯基4-喹啉酮生物碱喹诺内酯及其类似物的合成。此外，这种有机催化反应已成功用于以中等到良好的产率合成多种3-酰基-4-喹啉酮。包括时间进程核磁共振（NMR）实验在内的机理研究表明，9-AJ向炔酮体系的1,4-加成可被视为该喹啉酮合成中的速率决定步骤。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/d692e5d7d42a/ao-2017-00793h_0012.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/0e152dd51125/ao-2017-00793h_0004.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/d692e5d7d42a/ao-2017-00793h_0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/ac61d86777ef/ao-2017-00793h_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/a043725d609a/ao-2017-00793h_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/64207d808d24/ao-2017-00793h_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/b7d154b7ac37/ao-2017-00793h_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/613545ca52b2/ao-2017-00793h_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/fae5820bb168/ao-2017-00793h_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/7424353e4a17/ao-2017-00793h_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/0e152dd51125/ao-2017-00793h_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/50c27fcb8527/ao-2017-00793h_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/6508226e087c/ao-2017-00793h_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/12161a5a66e0/ao-2017-00793h_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0e6e/6641763/d692e5d7d42a/ao-2017-00793h_0012.jpg

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2
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3
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Molecules. 2019 Jan 4;24(1):164. doi: 10.3390/molecules24010164.
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Chem Pharm Bull (Tokyo). 2012;60(11):1458-60. doi: 10.1248/cpb.c12-00487. Epub 2012 Sep 4.
4
Quinolones: from antibiotics to autoinducers.喹诺酮类：从抗生素到自动诱导物。
FEMS Microbiol Rev. 2011 Mar;35(2):247-74. doi: 10.1111/j.1574-6976.2010.00247.x.
5
Penicinoline, a new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system from an endophytic fungus Penicillium sp.青霉素灵，一种新的吡咯并 4-喹啉酮生物碱，具有来自内生真菌青霉属的前所未有的环系统。
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6
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