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Synthesis 2014; 46(04): 496-502
DOI: 10.1055/s-0033-1338575
DOI: 10.1055/s-0033-1338575
paper
Synthesis of 6-Substituted 3-(Alkoxycarbonyl)-5-aryl-α-pyrones
Further Information
Publication History
Received: 22 October 2013
Accepted after revision: 18 November 2013
Publication Date:
16 December 2013 (online)
Abstract
An efficient synthesis of 6-substituted 3-(alkoxycarbonyl)-5-aryl-α-pyrones is reported. This methodology consists of the successive manipulation of an addition–elimination reaction between benzyl ketone derivatives and dimethyl methoxymethylenemalonate, and an acid-catalyzed condensation reaction. The synthesis is applicable to various 5-p-substituted-aryl 6-substituted α-pyrones and good to excellent yields were obtained over two steps from benzyl ketone derivatives that were easily prepared from phenylacetic acid by the Negishi coupling or the Claisen decarboxylation reaction.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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