Synthesis of 1,3-Dioxin-4-ones and Their Use in Synthesis.XVI. : 4-Oxo-1,3-dioxin-5-carboxylic Acids and Related Compounds : Versatile Synthetic Intermediates for the Synthesis of 6-Unsubstituted Six-Membered Heterocyclic Compunds

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概要

• 論文の詳細を見る

• A novel method for the synthesis of so far unknown 1,3-dioxin-4-ones having a carboxyl group at the 5-position is described. Reaction of formyl Meldrum's acid and an alcohol in an aprotic solvent at 50-60℃ gave the corresponding half esters of formylmalonic acid. Treatment of the latter with appropriate ketones in acetic anhydride containing a catalytic amount of p-toluenesulfonic acid gave the desired dioxinone-5-carboxylates.Successful conversion of these 1,3-dioxin-4-ones either to 1,3-oxazine-2,4-dione or uracil derivatives having an alkoxycarbonyl group at the 5-position demonstated that these dioxinones can serve as chemical equivalents for alkoxycarbonylformylketenes.The fact that 5-benzyloxycarbonyl-1,3-dioxin-4-one can readily be transformed to the so far unknown 5-aminodioxinone derivative indicates further the importance of the dioxinone having a carboxyl group at the 5-position as a new building block for heterocyclic compounds.

• 公益社団法人日本薬学会の論文
• 1989-03-25

著者

• 佐藤 雅之

  静岡県立大学薬学部

• 高山 和久

  Pharmaceutical Institute Tohoku University

• 金子 主税

  東北大学

• 金子 主税

  Pharmaceutical Institute Medical Faculty University Of Tokyo

• 佐藤 雅之

  Pharmaceutical Institute, Tohoku University

• 片桐 信弥

  Pharmaceutical Institute, Tohoku University

• 広瀬 正俊

  Pharmaceutical Institute, Tohoku University

• 片桐 信弥

  Health Sci. Univ. Hokkaido Hokkaido Jpn

• 片桐 信弥

  Pharmaceutical Institute Tohoku University

• 広瀬 正俊

  Pharmaceutical Institute Tohoku University

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