Sustainable Synthesis of 3-Acylmethylated Coumarins via Photoredox Catalytic Radical Addition/Cyclization in Aqueous Media

被引:0
作者
Zhu, Binfeng [1 ]
Ponnam, Devendar [1 ]
Li, Mingzhu [1 ]
Li, Guokai [1 ]
Fan, Ruifeng [1 ,2 ]
Chen, Jingchao [1 ,2 ]
Fan, Baomin [1 ,2 ]
机构
[1] Yunnan Minzu Univ, Yunnan Key Lab Chiral Funct Subst Res & Applicat, Kunming 650504, Peoples R China
[2] Yunnan Minzu Univ, Key Lab Chem Ethn Med Resources, Kunming 650500, Peoples R China
基金
中国国家自然科学基金;
关键词
ORGANIC-REACTIONS; ANTIINFLAMMATORY ACTIVITY; ARYL ALKYNOATES; BOND FORMATIONS; CYCLIZATION; WATER; CHEMISTRY; PHENOLS; DESIGN; ACCELERATION;
D O I
10.1021/acs.joc.5c00608
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A photoredox catalytic cascade radical reaction for the addition/cyclization of arylalkynoates with alpha-bromoketones in water at room temperature has been developed, offering a green and efficient approach for synthesizing 3-acylmethylated coumarins. This method eliminates the need for conventional organic solvents, phase-transfer catalysts, and excess oxidants, ensuring operational simplicity and environmental sustainability. The reaction is scalable, accommodates a broad array of substrates with outstanding tolerance for functional groups, and offers a versatile route to biologically valuable coumarins.
引用
收藏
页码:7738 / 7745
页数:8
相关论文
共 76 条
[1]   Anticancer therapeutic potential of benzofuran scaffolds [J].
Abbas, Ashraf A. ;
Dawood, Kamal M. .
RSC ADVANCES, 2023, 13 (16) :11096-11120
[2]   Synthesis and Antidepressant Activity of Some New Coumarin Derivatives [J].
Abdel-Latif, Nehad A. .
SCIENTIA PHARMACEUTICA, 2005, 73 (04) :195-216
[3]   Substituted 4-methylcoumarin inhibitors of SLC26A3 (DRA) for treatment of constipation and hyperoxaluria [J].
Ahmadi, Maria ;
Goncalves, Livia de Souza ;
Verkman, Alan S. ;
Cil, Onur ;
Anderson, Marc O. .
RSC MEDICINAL CHEMISTRY, 2024, 15 (05) :1731-1736
[4]   Coumarin: a potential nucleus for anti-inflammatory molecules [J].
Bansal, Yogita ;
Sethi, Purva ;
Bansal, Gulshan .
MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (07) :3049-3060
[5]   Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the knoevenagel synthesis of coumarin-3-carboxylic acids [J].
Bigi, F ;
Chesini, L ;
Maggi, R ;
Sartori, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :1033-1035
[6]   Development of a novel furocoumarin derivative inhibiting NF-κB dependent biological functions: Design, synthesis and biological effects [J].
Borgatti, Monica ;
Chilin, Adriana ;
Piccagli, Laura ;
Lampronti, Ilaria ;
Bianchi, Nicoletta ;
Mancini, Irene ;
Marzaro, Giovanni ;
dall'Acqua, Francesco ;
Guiotto, Adriano ;
Gambari, Roberto .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (10) :4870-4877
[7]  
Brahmachari G., 2021, GREEN SYNTHETIC APPR, P471, DOI [10.1016/B978-0-12-820792-5.00016-0, DOI 10.1016/B978-0-12-820792-5.00016-0]
[8]  
ccdc, XRAY CRYSTALLOGRAPHI
[9]   Alkoxy Radicals See the Light: New Paradigms of Photochemical Synthesis [J].
Chang, Liang ;
An, Qing ;
Duan, Lingfei ;
Feng, Kaixuan ;
Zuo, Zhiwei .
CHEMICAL REVIEWS, 2022, 122 (02) :2429-2486
[10]   Water as the reaction medium in organic chemistry: from our worst enemy to our best friend [J].
Cortes-Clerget, Margery ;
Yu, Julie ;
Kincaid, Joseph R. A. ;
Walde, Peter ;
Gallou, Fabrice ;
Lipshutz, Bruce H. .
CHEMICAL SCIENCE, 2021, 12 (12) :4237-4266