Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin via a TsOH-mediated tandem reaction

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 a...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-09, Vol.56 (71), p.10369-10372
Main Authors: Wang, Ding, Ma, Zhishuang, Wang, Nana, Li, Chenyu, Wang, Tao, Liang, Yong, Zhang, Zunting
Format: Article
Language:English
Subjects:
Acetone
Acetophenone
Aldehydes
Aromatic compounds
Benzene
Cascade chemical reactions
Coumarin
Crystallography
Cyano groups
Fluorescence
Friedel-Crafts reaction
Hydroxyl groups
Reagents
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Summary: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).
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc04452k