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锰(III)/钴(II)催化剂催化呋喃氧化——在苯并呋喃合成中的应用

Furan oxidation by Mn(iii)/Co(ii) catalysts - application to benzofuran synthesis.

作者信息

Wang Tingshu, Zhang Miao, Zheng Yifan, Seong Junmo, Lah Myoung Soo, Koo Sangho

机构信息

School of Pharmacy, East China University of Science and Technology Meilong Road 130 Shanghai 200237 P. R. of China.

Department of Energy Science and Technology, Myongji University Myongji-Ro 116, Cheoin-Gu Yongin Gyeonggi-Do 17058 Korea

出版信息

RSC Adv. 2021 Sep 22;11(50):31395-31399. doi: 10.1039/d1ra05305a. eCollection 2021 Sep 21.

DOI:10.1039/d1ra05305a
PMID:35496848
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9041371/
Abstract

Furans containing a β-ketoester group at 2-position undergo oxidative ring-opening by Mn(iii)/Co(ii) catalysts under an O atmosphere to produce 1,4-dicarbonyl moieties through an endoperoxide intermediate, which consecutively cyclized with the β-ketoester unit to afford 4-hydroxy-2-cyclohexen-1-ones. This oxidation/cyclization products were efficiently transformed into versatile benzofuran derivatives after consecutive aromatization and Paal-Knorr reaction.

摘要

在2-位含有β-酮酯基团的呋喃在O气氛下通过Mn(iii)/Co(ii)催化剂进行氧化开环,通过内过氧化物中间体生成1,4-二羰基部分,该中间体与β-酮酯单元连续环化,得到4-羟基-2-环己烯-1-酮。经过连续的芳构化和帕尔-克诺尔反应后,这种氧化/环化产物被有效地转化为多功能苯并呋喃衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3216/9041371/e30547a893de/d1ra05305a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3216/9041371/b0bcac2def79/d1ra05305a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3216/9041371/faa08acb0216/d1ra05305a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3216/9041371/672dc8c48890/d1ra05305a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3216/9041371/e30547a893de/d1ra05305a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3216/9041371/b0bcac2def79/d1ra05305a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3216/9041371/faa08acb0216/d1ra05305a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3216/9041371/672dc8c48890/d1ra05305a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3216/9041371/e30547a893de/d1ra05305a-s4.jpg

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本文引用的文献

1
Natural source, bioactivity and synthesis of benzofuran derivatives.苯并呋喃衍生物的天然来源、生物活性及合成
RSC Adv. 2019 Sep 2;9(47):27510-27540. doi: 10.1039/c9ra04917g. eCollection 2019 Aug 29.
2
Tandem catalytic oxidative deacetylation of acetoacetic esters and heteroaromatic cyclizations.乙酰乙酸酯的串联催化氧化脱乙酰化反应及杂芳环化反应。
Org Biomol Chem. 2015 Mar 7;13(9):2588-99. doi: 10.1039/c4ob02441a.
3
Bioactive Benzofuran derivatives: A review.生物活性苯并呋喃衍生物:综述。
Eur J Med Chem. 2015 Jun 5;97:483-504. doi: 10.1016/j.ejmech.2014.11.039. Epub 2014 Nov 22.
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Bioactive benzofuran derivatives: moracins A-Z in medicinal chemistry.生物活性苯并呋喃衍生物:药物化学中的莫拉辛A至Z
Eur J Med Chem. 2015 Jan 27;90:379-93. doi: 10.1016/j.ejmech.2014.11.047. Epub 2014 Nov 25.
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Using singlet oxygen to synthesize polyoxygenated natural products from furans.利用单线态氧从呋喃合成多氧化天然产物。
Acc Chem Res. 2008 Aug;41(8):1001-11. doi: 10.1021/ar800023v. Epub 2008 Jul 8.
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Furan ring oxidation strategy for the synthesis of macrosphelides A and B.
J Org Chem. 2001 Mar 23;66(6):2011-8. doi: 10.1021/jo001495d.
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A simple, efficient, and general method for the conversion of alcohols into alkyl iodides by a CeCl3.7H2O/NaI system in acetonitrile.一种在乙腈中通过CeCl₃·7H₂O/NaI体系将醇转化为烷基碘的简单、高效且通用的方法。
J Org Chem. 2000 May 9;65(9):2830-3. doi: 10.1021/jo991894c.
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Pharmacokinetic study of paeonimetabolin I, a major metabolite of paeoniflorin from paeony roots.芍药根中芍药苷主要代谢产物芍药代谢物I的药代动力学研究
Biol Pharm Bull. 1997 May;20(5):517-21. doi: 10.1248/bpb.20.517.