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Authors: Maebayashi H, Takano A, Sato M, Manabe K, Iwamoto K
Publication date: 2009
Article title: Synthesis of 4-Hydroxy-2-pyrone Derivatives and Application to Ion Imprinting Polymers.
Alternative URL: https://www.jstage.jst.go.jp/article/hannou/35/0/35_0_131/_article
Volume number: 35
Conference information: 35th Symposium on Progress in Organic Reactions and Syntheses
Abstract: 1,3-Dioxin-4-one derivatives provide acylated ketenes with releasing of acetone by heating. 1,3-Dioxin-4-one derivatives are very useful synthons for organic synthesis as equivalents of mixed diketene. Acylated ketenes easily dimerize to be chelatable dehydroacetic acid derivatives. We discovered two synthetic routes for 1,3-dioxin-4-one derivatives. 1) Acylation of Meldrum's acid, and ring transformation by heating following decarboxylation afford 1,3-dioxin-4-one derivatives in three steps. 2) Cross-coupling reaction of 6-bromomethyl-2,2-dimethyl-1,3-dioxin-4-one with Grignard reagents in the presence of metal catalyst also gave target derivatives. Based on above synthetic method, we examine to utilize dehydroacetic acid derivatives for Ion Imprinting Polymers (IIPs) as the templates.
Author keywords: Cross-coupling, ring transformation, Chelate, IIP
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