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

• DOI: 10.1021/acs.orglett.8b02269
• Publication Date: 2018-08-28T01:42:11Z
• Authors: Singam Naveen Kumar; Suhas Ravindra Ba...; Chebolu Naga Sesh...; Isaac Furay Yu; Rong-Jie Chein
• Keywords: Fries rearrangement; Chalcone; Carroll rearrangement; Carbamate; Rearrangement reaction; Cope rearrangement; Condensation reaction

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 and Claisen–Schmidt condensation in a single operation. The applicability this protocol demonstrated by anti-inflammatory natural product lonchocarpin. mechanism insight is also provided.