Synthesis of V‐Shaped Bis‐coumarins through Aldol Reaction/Double Lactonization Cascade Reaction from Bis(2‐hydroxyphenyl)methanone and Meldrum's Acid

A concise and efficient method was developed for the synthesis of chromeno[3,4‐c]chromene‐6,7‐dione using readily available bis(2‐hydroxyphenyl)methanone and Meldrum's acid. The protocol displays a broad substrate scope and good functional group tolerance, including alkyl, alkoxyl, aryl, and ha...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-04, Vol.2022 (13), p.n/a
Main Authors: Wang, Ding, Ma, Zhishuang, Xi, Jin, Wang, Nana, Wang, Tao, Liang, Yong, Zhang, Zunting
Format: Article
Language:English
Subjects:
Aldehydes
Bis-coumarins
Cascade chemical reactions
Cascade reaction
Diketones
Fluorescence spectroscopy
Functional groups
Halogens
Meldrum's acid
Substrates
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Summary:A concise and efficient method was developed for the synthesis of chromeno[3,4‐c]chromene‐6,7‐dione using readily available bis(2‐hydroxyphenyl)methanone and Meldrum's acid. The protocol displays a broad substrate scope and good functional group tolerance, including alkyl, alkoxyl, aryl, and halogens. These π‐extended scaffolds showed blue‐green fluorescence with a large Stokes shift. The photophysical studies revealed that 2‐position substituted chromeno[3,4‐c]chromene‐6,7‐dione caused a significant bathochromic shift. A series of π‐expanded coumarins derivatives, chromeno[3,4‐c]chromene‐6,7‐diones, were synthesized using bis(2‐hydroxyphenyl)methanone and Meldrum's acid through a PhSO3H‐mediated cascade reaction. The protocol displays a broad substrate scope and exhibits excellent functional group tolerance.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101489