80427-38-9Relevant academic research and scientific papers
Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarinviaa TsOH-mediated tandem reaction
Li, Chenyu,Liang, Yong,Ma, Zhishuang,Wang, Ding,Wang, Nana,Wang, Tao,Zhang, Zunting
supporting information, p. 10369 - 10372 (2020/09/16)
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).
Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
Miao, Jianzhuang,Cui, Huaqing,Jin, Jing,Lai, Fangfang,Wen, Hui,Zhang, Xiang,Ruda, Gian Filippo,Chen, Xiaoguang,Yin, Dali
supporting information, p. 881 - 884 (2015/02/19)
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
An improved synthesis of hydroxy aryl ketones by fries rearrangement with methanesulfonic acid/methanesulfonic anhydride
Jeon, Ingyu,Mangion, Ian K.
experimental part, p. 1927 - 1930 (2012/10/08)
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.
NOVEL KINASE MODULATORS
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Page/Page column 87, (2011/06/10)
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.
Studies on the Friedel-Crafts Reaction. XVI, Preparation of Isomeric 2-Acyl- and 3-Acyl-4-methoxy Phenols
Martin, Robert
, p. 1155 - 1164 (2007/10/02)
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
