Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines Full article
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Molecules
ISSN: 1420-3049 |
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| Output data | Year: 2023, Volume: 28, Number: 7, Article number : 3139, Pages count : DOI: 10.3390/molecules28073139 | ||
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Abstract:
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(1H)-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)-5H-chromeno[2,3-b]pyridines in DMSO. Previously unknown 5,7-dihalogenated 5-(2,3,4,9-tetrahydro-1H-xanthen-9-yl)-6-oxo-1,6-dihydropyridines and 10-(3,5-dihalogen-2-hydroxyphenyl)-5,6,7,8,9,10-hexahydrobenzo[b][1,6]naphthyridines were synthesized with excellent yields (90–99%). The investigation of the transformation using 1H-NMR monitoring made it possible to confirm the ANRORC mechanism. The structures of synthesized compounds were confirmed by 2D-NMR spectroscopy.
Cite:
Ryzhkova Y.E.
, Ryzhkov F.V.
, Elinson M.N.
, Vereshchagin A.N.
, Novikov R.A.
, Fakhrutdinov A.N.
Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines
Molecules. 2023. V.28. N7. 3139 . DOI: 10.3390/molecules28073139 WOS Scopus OpenAlex
Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines
Molecules. 2023. V.28. N7. 3139 . DOI: 10.3390/molecules28073139 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000969938600001 |
| Scopus: | 2-s2.0-85152346935 |
| OpenAlex: | W4362579390 |
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