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

Yuliya E Ryzhkova,Michail N Elinson,Fedor V Ryzhkov,Varvara M Kalashnikova

doi:10.3390/m1317

Yuliya E Ryzhkova, Michail N Elinson + Show 2 more

Open Access

https://doi.org/10.3390/m1317

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Journal: Molbank	Publication Date: Jan 14, 2022
Citations: 2	License type: CC BY 4.0

Affiliation: N.D. Zelinsky Institute of Organic Chemistry

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.

Highlights

Michaelinitiated ring closure (MIRC) reactions a nucleophile with a well-leaving group is added to the substrate, which is necessary for further cyclization [2]
In the Michael addition–halogenation–intramolecular ring-closing (MHIRC) strategy the halogen atom as a leaving group can attach to substrates or reactants during the reaction, which undergoes intramolecular ring closure [3]
Barbituric acid has been utilized in the design and synthesis of diverse different types of heterocyclic and carbocyclic compounds, and is considered to be an important building block in organic synthesis [5]

Summary

Discussion

MHIRC transformations including electrochemWe transformations including electrochemical ical transformations [14,15,16,17]. In these reactions the source of the well-leaving group was was transformations [14,15,16,17]. In these reactions the source of the well-leaving group molecular bromine, bromine, which which was was either either formed formed during during electrolysis electrolysis or or was was added added directly directly as as molecular reagent.

Reaction

General Methods

Conclusions