1,3-Dimethyl-3′,5-diphenyl-1,5-dihydro-2<i>H</i>,5′<i>H</i>-spiro[furo[2,3-<i>d</i>]pyrimidine-6,4′-isoxazole]-2,4,5′(3<i>H</i>)-trione

Abstract

Michael addition–halogenation–intramolecular ring-closing (MHIRC) reactions are processes in which a halogen atom as a leaving group can attach to substrates or reactants during the reaction, which then undergoes intramolecular ring closure. In this communication the MHIRC transformation of 4-benzylidene-3-phenylisoxazol-5(4H)-one and 1,3-dimethylbarbituric acid in the presence of N-bromosuccinimide and sodium acetate in EtOH at room temperature was carefully investigated to give novel 1,3-dimethyl-3′,5-diphenyl-1,5-dihydro-2H,5′H-spiro[furo[2,3-d]pyrimi- dine-6,4′-isoxazole]-2,4,5′(3H)-trione in a good yield. The structure of the new compound was confirmed by the results of elemental analysis as well as mass, nuclear magnetic resonance, and infrared spectroscopy.

Keywords

• 4-benzylidene-3-phenylisoxazol-5(4<i>H</i>)-one
• 1,3-dimethylbarbituric acid
• spiro[furo[2,3-<i>d</i>]pyrimidine]
• <i>N</i>-bromosuccinimide
• MHIRC process