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
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-benzyl...
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MDPI AG
2022-01-01
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| Online Access: | https://www.mdpi.com/1422-8599/2022/1/M1317 |
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| author | Yuliya E. Ryzhkova Varvara M. Kalashnikova Fedor V. Ryzhkov Michail N. Elinson |
| author_facet | Yuliya E. Ryzhkova Varvara M. Kalashnikova Fedor V. Ryzhkov Michail N. Elinson |
| author_sort | Yuliya E. Ryzhkova |
| collection | DOAJ |
| description | 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(4<i>H</i>)-one and 1,3-dimethylbarbituric acid in the presence of <i>N</i>-bromosuccinimide and sodium acetate in EtOH at room temperature was carefully investigated to give novel 1,3-dimethyl-3′,5-diphenyl-1,5-dihydro-2<i>H</i>,5′<i>H</i>-spiro[furo[2,3-<i>d</i>]pyrimi- dine-6,4′-isoxazole]-2,4,5′(3<i>H</i>)-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. |
| first_indexed | 2024-03-09T13:13:40Z |
| format | Article |
| id | doaj.art-f3be5b20a47046f780514b458d1efa08 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T13:13:40Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-f3be5b20a47046f780514b458d1efa082023-11-30T21:39:16ZengMDPI AGMolbank1422-85992022-01-0120221M131710.3390/M13171,3-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>)-trioneYuliya E. Ryzhkova0Varvara M. Kalashnikova1Fedor V. Ryzhkov2Michail N. Elinson3N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, RussiaMichael 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(4<i>H</i>)-one and 1,3-dimethylbarbituric acid in the presence of <i>N</i>-bromosuccinimide and sodium acetate in EtOH at room temperature was carefully investigated to give novel 1,3-dimethyl-3′,5-diphenyl-1,5-dihydro-2<i>H</i>,5′<i>H</i>-spiro[furo[2,3-<i>d</i>]pyrimi- dine-6,4′-isoxazole]-2,4,5′(3<i>H</i>)-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.https://www.mdpi.com/1422-8599/2022/1/M13174-benzylidene-3-phenylisoxazol-5(4<i>H</i>)-one1,3-dimethylbarbituric acidspiro[furo[2,3-<i>d</i>]pyrimidine]<i>N</i>-bromosuccinimideMHIRC process |
| spellingShingle | Yuliya E. Ryzhkova Varvara M. Kalashnikova Fedor V. Ryzhkov Michail N. Elinson 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 Molbank 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 |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | 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 |
| url | https://www.mdpi.com/1422-8599/2022/1/M1317 |
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