- Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarinviaa TsOH-mediated tandem reaction
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A concise and efficient method for the synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin using available 1-(2-hydroxyphenyl)-2-phenylethanone and Meldrum's acid has been developed. This transformation involved a tandem aldol reaction/lactonization/Friedel-Crafts reaction to form a lactone ring and a benzene ring. It showed high atom economy with water and acetone as the byproducts. Mechanism studies demonstrated two roles of Meldrum's acid: (i) as the reagent for the tandem reaction, and (ii) as the catalyst for the Friedel-Crafts reaction. Moreover, the hydroxyl group of 7-hydroxy-6H-naphtho[2,3-c]coumarin was further functionalized efficiently by arylethynyl, aryl, and cyano groups to furnish D-π-A compounds with excellent fluorescence emissions (ΦF= 0.14-0.78).
- Li, Chenyu,Liang, Yong,Ma, Zhishuang,Wang, Ding,Wang, Nana,Wang, Tao,Zhang, Zunting
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p. 10369 - 10372
(2020/09/16)
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- Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
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Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ~ 205.19, λab ~ 350 nm, λem ~ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is
- Miao, Jianzhuang,Cui, Huaqing,Jin, Jing,Lai, Fangfang,Wen, Hui,Zhang, Xiang,Ruda, Gian Filippo,Chen, Xiaoguang,Yin, Dali
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supporting information
p. 881 - 884
(2015/02/19)
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- An improved synthesis of hydroxy aryl ketones by fries rearrangement with methanesulfonic acid/methanesulfonic anhydride
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Methanesulfonic acid treated with methanesulfonic anhydride effectively mediates the Fries rearrangement of aryl esters to give hydroxy aryl ketones with high yields. Georg Thieme Verlag Stuttgart · New York.
- Jeon, Ingyu,Mangion, Ian K.
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experimental part
p. 1927 - 1930
(2012/10/08)
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- NOVEL KINASE MODULATORS
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The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.
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Page/Page column 87
(2011/06/10)
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- Studies on the Friedel-Crafts Reaction. XVI, Preparation of Isomeric 2-Acyl- and 3-Acyl-4-methoxy Phenols
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Acylation of 4-methoxy phenol according to Friedel and Crafts, as well as the rearrangement of its esters according to Fries lead always to 2-acyl-4-methoxy phenols or to their demethylated compounds.The unknown 3-acyl-4-methoxyphenols were prepared in two steps: First, the ester is acylated with the corresponding acyl chloride and SnCl4 in nitromethane.In the second step the resulting ketoesters are hydrolysed.This is a general method.The yields of meta-acylphenols are between 40 and 90percent.The isomeric 2-acyl-4-methoxyphenols which were partly unknown or accessible only in low yields have also been prepared for comparative spectral studies (UV, IR, NMR, MS) of ortho- and meta-acylphenols. - Keywords: Friedel-Crafts acylation; Fries rearrangement; Ketoesters; Spectral data
- Martin, Robert
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p. 1155 - 1164
(2007/10/02)
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