1,3-Dimethyl-3′,5-diphenyl-1,5-dihydro-2H,5′H-spiro[furo[2,3-d]pyrimidine-6,4′-isoxazole]-2,4,5′(3H)-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.

Furo, Pyrano, and Pyrido[2,3‐d]Pyrimidines: A Comprehensive Review of Synthesis and Medicinal Applications

“…In a recent study published in 2022, Ryzhkova and colleagues [135] made a significant contribution to the field of organic synthesis. They utilized the MHIRC process to synthesize a novel compound, 1,3‐Dimethyl‐3′,5‐diphenyl‐1,5‐dihydro‐2 H ,5′ H ‐spiro[furo[2,3‐ d ]pyrimidine‐6,4′‐isoxazole]‐2,4,5′(3 H )‐triones 209 .The MHIRC process, known for its efficiency in synthesizing complex organic compounds, was effectively employed by the team to create this unique compound.…”

Review on synthetic approaches towards barbituric acids‐based furo[2,3‐d]pyrimidines

“…An intramolecular. O ‐attack of the hydroxy group to the electrophilic bromo substituted carbon atom gives the desired product 134 [66].…”