123798-22-1Relevant academic research and scientific papers
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 INTERMEDIATES FOR THE SYNTHESIS OF 6-UNSUBSTITUTED SIX-MEMBERED HETEROCYCLIC COMPOUNDS
Sato, Masayuki,Katagiri, Nobuya,Takayama, Kazuhisa,Hirose, Masatoshi,Kaneko, Chikara
, p. 665 - 669 (2007/10/02)
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 deg C 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 demonstrated 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.Keywords: 4-oxo-1,3-dioxin-5-carboxylic acid; formylmalonic acid half ester; Meldrum's acid; 5-amino-1,3-dioxin-4-one; cycloaddition; 4-oxo-1,3-oxazine-5-carboxylate; 2-dimethylamino-1,3-oxazin-4-one; alkoxycarbonylformylketene
