From Carbamate to Chalcone: Consecutive Anionic Fries Rearrangement, Anionic Si → C Alkyl Rearrangement, and Claisen–Schmidt Condensation

A highly efficient one-pot procedure was developed for the synthesis of various 2′-hydroxychalcones from phenyl diethylcarbamate, featuring consecutive Snieckus–Fries rearrangement, anionic Si → C alkyl rearrangement, and Claisen–Schmidt condensation in a single operation. The applicability of this...

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Bibliographic Details
Published in:Organic letters 2018-09, Vol.20 (17), p.5362-5366
Main Authors: Kumar, Singam Naveen, Bavikar, Suhas Ravindra, Pavan Kumar, Chebolu Naga Sesha Sai, Yu, Isaac Furay, Chein, Rong-Jie
Format: Article
Language:English
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Summary:A highly efficient one-pot procedure was developed for the synthesis of various 2′-hydroxychalcones from phenyl diethylcarbamate, featuring consecutive Snieckus–Fries rearrangement, anionic Si → C alkyl rearrangement, and Claisen–Schmidt condensation in a single operation. The applicability of this protocol was demonstrated by the highly efficient synthesis of the anti-inflammatory natural product lonchocarpin. The mechanism insight is also provided.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02269