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Synthesis of 6-Substituted 3-(Alkoxycarbonyl)-5-aryl-α-pyrones

Takuya Miura, Saki Fujioka, Naoto Takemura, Hiroki Iwasaki, Minoru Ozeki, Naoto Kojima, Masayuki Yamashita*

*Kyoto Pharmaceutical University, 1 Misasagi-Shichono, Yamashina, Kyoto 607-8412, Japan, Email: yamasitamb.kyoto-phu.ac.jp

T. Miura, S. Fujioka, N. Takemura, H. Iwasaki, M. Ozeki, N. Kojima, M. Yamashita, Synthesis, 2014, 46, 496-502.

DOI: 10.1055/s-0033-1338575 (free Supporting Information)


Abstract

An efficient synthesis of 6-substituted 3-(alkoxycarbonyl)-5-aryl-α-pyrones consists of an addition-elimination reaction between benzyl ketone derivatives and dimethyl methoxymethylenemalonate, and an acid-catalyzed condensation reaction. The synthesis is applicable to various multiubstituted α-pyrones in very good yields.

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Key Words

α-pyrones, heterocycles, 1,4-addition, condensation, ketones


ID: J66-Y2014