4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione
An environment-friendly photochemical approach to the synthesis of 4a,7a-dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione from 2-(4-(3-hydroxy-6-methyl-4-oxo-4<i>H&...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-11-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2022/4/M1481 |
| _version_ | 1797456071421329408 |
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| author | Andrey N. Komogortsev Boris V. Lichitsky Valeriya G. Melekhina |
| author_facet | Andrey N. Komogortsev Boris V. Lichitsky Valeriya G. Melekhina |
| author_sort | Andrey N. Komogortsev |
| collection | DOAJ |
| description | An environment-friendly photochemical approach to the synthesis of 4a,7a-dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione from 2-(4-(3-hydroxy-6-methyl-4-oxo-4<i>H</i>-pyran-2-yl)tetrahydro-2<i>H</i>-pyran-4-yl)-<i>N</i>-(2-hydroxyethyl)acetamide was elaborated. The suggested method is based on the ESIPT-promoted contraction of 3-hydroxypyran-4-one fragment followed by intramolecular cyclization of generated in situ α-hydroxy-1,2-diketone intermediate. The distinctive feature of the presented protocol is the employment of water as a solvent for the considered photoreaction. The structure of the obtained photoproduct was confirmed by <sup>1</sup>H, <sup>13</sup>C-NMR, IR spectroscopy and high-resolution mass spectrometry. |
| first_indexed | 2024-03-09T16:03:08Z |
| format | Article |
| id | doaj.art-514f2cb72a9e40f9a8339ff3a2e0bfb2 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T16:03:08Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-514f2cb72a9e40f9a8339ff3a2e0bfb22023-11-24T16:54:01ZengMDPI AGMolbank1422-85992022-11-0120224M148110.3390/M14814a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dioneAndrey N. Komogortsev0Boris V. Lichitsky1Valeriya G. Melekhina2N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, 119991 Moscow, RussiaAn environment-friendly photochemical approach to the synthesis of 4a,7a-dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione from 2-(4-(3-hydroxy-6-methyl-4-oxo-4<i>H</i>-pyran-2-yl)tetrahydro-2<i>H</i>-pyran-4-yl)-<i>N</i>-(2-hydroxyethyl)acetamide was elaborated. The suggested method is based on the ESIPT-promoted contraction of 3-hydroxypyran-4-one fragment followed by intramolecular cyclization of generated in situ α-hydroxy-1,2-diketone intermediate. The distinctive feature of the presented protocol is the employment of water as a solvent for the considered photoreaction. The structure of the obtained photoproduct was confirmed by <sup>1</sup>H, <sup>13</sup>C-NMR, IR spectroscopy and high-resolution mass spectrometry.https://www.mdpi.com/1422-8599/2022/4/M1481allomaltolESIPT-processphotochemical transformationsgreen chemistry |
| spellingShingle | Andrey N. Komogortsev Boris V. Lichitsky Valeriya G. Melekhina 4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione Molbank allomaltol ESIPT-process photochemical transformations green chemistry |
| title | 4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione |
| title_full | 4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione |
| title_fullStr | 4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione |
| title_full_unstemmed | 4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione |
| title_short | 4a,7a-Dihydroxy-1-(2-hydroxyethyl)-5-methyl-2′,3′,4a,5′,6′,7a-hexahydrospiro[cyclopenta[<i>b</i>]pyridine-4,4′-pyran]-2,7(1<i>H</i>,3<i>H</i>)-dione |
| title_sort | 4a 7a dihydroxy 1 2 hydroxyethyl 5 methyl 2 3 4a 5 6 7a hexahydrospiro cyclopenta i b i pyridine 4 4 pyran 2 7 1 i h i 3 i h i dione |
| topic | allomaltol ESIPT-process photochemical transformations green chemistry |
| url | https://www.mdpi.com/1422-8599/2022/4/M1481 |
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