Base‐Promoted Direct Cascade Transformation of Chromones to Coumarins via Benzannulation and Transesterification

A mild base‐promoted reaction between 3‐substituted chromones and β‐keto esters for the easy access to various coumarins with structural diversity is described. This protocol provides highly functionalized 3‐acyl‐4‐arylcoumarins in good‐to‐excellent yield via benzannulation and transesterification....

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Bibliographic Details
Published in:Asian journal of organic chemistry 2021-04, Vol.10 (4), p.827-830
Main Authors: Cai, Hongyun, Khanal, Hari Datta, Lee, Yong Rok
Format: Article
Language:English
Subjects:
annulation
chromones
Esters
Organic chemistry
oxygen heterocycles
Reaction mechanisms
Transesterification
β-keto ester
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Description
Summary:A mild base‐promoted reaction between 3‐substituted chromones and β‐keto esters for the easy access to various coumarins with structural diversity is described. This protocol provides highly functionalized 3‐acyl‐4‐arylcoumarins in good‐to‐excellent yield via benzannulation and transesterification. A reaction mechanism containing Michael addition, 1,5‐H shift and intramolecular transesterification is proposed. Improved route to 3‐acyl‐4‐arylcoumarins: An efficient methodology for the synthesis of diversely functionalized 3‐acyl‐4‐arylcoumarins through the mild base‐promoted reaction of 3‐substituted chromen‐4‐ones with β‐keto esters via cascade benzannulation and transesterification is developed.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202100039