3-Benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone
We describe an approach towards the synthesis of previously unknown 3-benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone. The presen...
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2025-01-01
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| author | Michail N. Elinson Varvara M. Kalashnikova Yuliya E. Ryzhkova Oleg A. Rakitin |
| author_facet | Michail N. Elinson Varvara M. Kalashnikova Yuliya E. Ryzhkova Oleg A. Rakitin |
| author_sort | Michail N. Elinson |
| collection | DOAJ |
| description | We describe an approach towards the synthesis of previously unknown 3-benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone. The presented method is based on the cyclization of 5-(1-(4-hydroxy-6-methyl-2-oxo-2<i>H</i>-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1<i>H</i>,3<i>H</i>,5<i>H</i>)-trione. It was shown that the presented reaction proceeds through the stage of bromination of the starting compound followed by <i>O</i>-nucleophilic attack. The structures of the obtained compound were established by <sup>1</sup>H, <sup>13</sup>C NMR and IR spectroscopy, and high-resolution mass spectrometry. |
| format | Article |
| id | doaj-art-abff0195fa264874bb8c59b14a56db63 |
| institution | DOAJ |
| issn | 1422-8599 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj-art-abff0195fa264874bb8c59b14a56db632025-08-20T02:42:28ZengMDPI AGMolbank1422-85992025-01-0120251M195110.3390/M19513-Benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraoneMichail N. Elinson0Varvara M. Kalashnikova1Yuliya E. Ryzhkova2Oleg A. Rakitin3N. 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, RussiaWe describe an approach towards the synthesis of previously unknown 3-benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone. The presented method is based on the cyclization of 5-(1-(4-hydroxy-6-methyl-2-oxo-2<i>H</i>-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1<i>H</i>,3<i>H</i>,5<i>H</i>)-trione. It was shown that the presented reaction proceeds through the stage of bromination of the starting compound followed by <i>O</i>-nucleophilic attack. The structures of the obtained compound were established by <sup>1</sup>H, <sup>13</sup>C NMR and IR spectroscopy, and high-resolution mass spectrometry.https://www.mdpi.com/1422-8599/2025/1/M1951spiro[furo[3,2-<i>c</i>]pyran-2,5?-pyrimidine]<i>N</i>-bromosuccinimidesodium acetatecyclization |
| spellingShingle | Michail N. Elinson Varvara M. Kalashnikova Yuliya E. Ryzhkova Oleg A. Rakitin 3-Benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone Molbank spiro[furo[3,2-<i>c</i>]pyran-2,5?-pyrimidine] <i>N</i>-bromosuccinimide sodium acetate cyclization |
| title | 3-Benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone |
| title_full | 3-Benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone |
| title_fullStr | 3-Benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone |
| title_full_unstemmed | 3-Benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone |
| title_short | 3-Benzoyl-1′,3′,6-trimethyl-2′<i>H</i>,3<i>H</i>,4<i>H</i>-spiro[furo[3,2-<i>c</i>]pyran-2,5′-pyrimidine]-2′,4,4′,6′(1′<i>H</i>,3′<i>H</i>)-tetraone |
| title_sort | 3 benzoyl 1 3 6 trimethyl 2 i h i 3 i h i 4 i h i spiro furo 3 2 i c i pyran 2 5 pyrimidine 2 4 4 6 1 i h i 3 i h i tetraone |
| topic | spiro[furo[3,2-<i>c</i>]pyran-2,5?-pyrimidine] <i>N</i>-bromosuccinimide sodium acetate cyclization |
| url | https://www.mdpi.com/1422-8599/2025/1/M1951 |
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