Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines
Some of the most important transformations in organic chemistry are rearrangement reactions, which play a crucial role in increasing synthetic efficiency and molecular complexity. The development of synthetic strategies involving rearrangement reactions, which can accomplish synthetic goals in a ver...
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MDPI AG
2023-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/7/3139 |
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| author | Yuliya E. Ryzhkova Fedor V. Ryzhkov Michail N. Elinson Anatoly N. Vereshchagin Roman A. Novikov Artem N. Fakhrutdinov |
| author_facet | Yuliya E. Ryzhkova Fedor V. Ryzhkov Michail N. Elinson Anatoly N. Vereshchagin Roman A. Novikov Artem N. Fakhrutdinov |
| author_sort | Yuliya E. Ryzhkova |
| collection | DOAJ |
| description | Some of the most important transformations in organic chemistry are rearrangement reactions, which play a crucial role in increasing synthetic efficiency and molecular complexity. The development of synthetic strategies involving rearrangement reactions, which can accomplish synthetic goals in a very efficient manner, has been an evergreen topic in the synthetic chemistry community. Xanthenes, pyridin-2(1<i>H</i>)-ones, and 1,6-naphthyridines have a wide range of biological activities. In this work, we propose the thermal rearrangement of 7,9-dihalogen-substituted 5-(2-hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines in DMSO. Previously unknown 5,7-dihalogenated 5-(2,3,4,9-tetrahydro-1<i>H</i>-xanthen-9-yl)-6-oxo-1,6-dihydropyridines and 10-(3,5-dihalogen-2-hydroxyphenyl)-5,6,7,8,9,10-hexahydrobenzo[<i>b</i>][1,6]naphthyridines were synthesized with excellent yields (90–99%). The investigation of the transformation using <sup>1</sup>H-NMR monitoring made it possible to confirm the ANRORC mechanism. The structures of synthesized compounds were confirmed by 2D-NMR spectroscopy. |
| first_indexed | 2024-03-11T05:29:55Z |
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| id | doaj.art-9e343c0f93dc4870ad32ad16df10d988 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T05:29:55Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9e343c0f93dc4870ad32ad16df10d9882023-11-17T17:14:11ZengMDPI AGMolecules1420-30492023-03-01287313910.3390/molecules28073139Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridinesYuliya E. Ryzhkova0Fedor V. Ryzhkov1Michail N. Elinson2Anatoly N. Vereshchagin3Roman A. Novikov4Artem N. Fakhrutdinov5N. 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, 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, RussiaSome of the most important transformations in organic chemistry are rearrangement reactions, which play a crucial role in increasing synthetic efficiency and molecular complexity. The development of synthetic strategies involving rearrangement reactions, which can accomplish synthetic goals in a very efficient manner, has been an evergreen topic in the synthetic chemistry community. Xanthenes, pyridin-2(1<i>H</i>)-ones, and 1,6-naphthyridines have a wide range of biological activities. In this work, we propose the thermal rearrangement of 7,9-dihalogen-substituted 5-(2-hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines in DMSO. Previously unknown 5,7-dihalogenated 5-(2,3,4,9-tetrahydro-1<i>H</i>-xanthen-9-yl)-6-oxo-1,6-dihydropyridines and 10-(3,5-dihalogen-2-hydroxyphenyl)-5,6,7,8,9,10-hexahydrobenzo[<i>b</i>][1,6]naphthyridines were synthesized with excellent yields (90–99%). The investigation of the transformation using <sup>1</sup>H-NMR monitoring made it possible to confirm the ANRORC mechanism. The structures of synthesized compounds were confirmed by 2D-NMR spectroscopy.https://www.mdpi.com/1420-3049/28/7/3139rearrangementNMR studychromeno[2,3-<i>b</i>]pyridinedimethyl sulfoxide2,3,4,9-tetrahydro-1<i>H</i>-xanthene5,6,7,8,9,10-hexahydrobenzo[<i>b</i>][1,6]naphthyridine |
| spellingShingle | Yuliya E. Ryzhkova Fedor V. Ryzhkov Michail N. Elinson Anatoly N. Vereshchagin Roman A. Novikov Artem N. Fakhrutdinov Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines Molecules rearrangement NMR study chromeno[2,3-<i>b</i>]pyridine dimethyl sulfoxide 2,3,4,9-tetrahydro-1<i>H</i>-xanthene 5,6,7,8,9,10-hexahydrobenzo[<i>b</i>][1,6]naphthyridine |
| title | Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines |
| title_full | Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines |
| title_fullStr | Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines |
| title_full_unstemmed | Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines |
| title_short | Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines |
| title_sort | thermal rearrangement of 5 2 hydroxy 6 oxocyclohexyl 5 i h i chromeno 2 3 i b i pyridines |
| topic | rearrangement NMR study chromeno[2,3-<i>b</i>]pyridine dimethyl sulfoxide 2,3,4,9-tetrahydro-1<i>H</i>-xanthene 5,6,7,8,9,10-hexahydrobenzo[<i>b</i>][1,6]naphthyridine |
| url | https://www.mdpi.com/1420-3049/28/7/3139 |
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