Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines
Abstract
:1. Introduction
2. Results and Discussion
2.1. Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines
2.2. The 1H-NMR Monitoring of Thermal Rearrangement
2.3. Confirmation of the Structure of the Synthesized 2,3,4,9-Tetrahydro-1H-xanthenes 2 and 5,6,7,8,9,10-Hexahydrobenzo[b][1,6]naphthyridines 3
3. Materials and Methods
3.1. General Methods
3.2. Thermal Rearrangement of 7,9-Dihalogenated 5-(2-Hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles 1 at 100 °C
3.3. Thermal Rearrangement of 7,9-Dihalogenated 5-(2-Hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles 1 at 150 °C
3.4. Thermal Rearrangement of 5,7-Dihalogenated 5-(1-oxo-2,3,4,9-tetrahydro-1H-xanthen-9-yl)-6-oxo-1,6-dihydropyridine-3-carbonitriles 2 at 150 °C
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Entry | Solvent, mL | Temperature, °C | Time, h | Yield of 2a, % | Yield of 3a, % |
---|---|---|---|---|---|
1 | DMSO, 0.5 | 100 | 1 | 99 2 | – |
2 | DMSO, 0.5 | 120 | 1 | 88 | 10 |
3 | DMSO, 0.5 | 150 | 1 | – | 98 2 |
4 | DMF, 0.5 | 100 | 1 | 95 2 | – |
5 | DMF, 0.5 | 150 | 1 | – | 94 2 |
6 | H2O, 2 | 100 | 1 | 6 | 5 |
7 | MeCN, 0.5 | 82 | 1 | 8 | – |
8 | n-PrOH, 0.5 | 97 | 1 | 25 | – |
9 | Dioxane, 0.5 | 101 | 1 | – | – |
10 | DMSO, 0.5 | 100 | 0.5 | 82 2 | – |
11 | DMSO, 0.5 | 150 | 0.5 | – | 80 2 |
Entry | Chromeno[2,3-b]pyridine 1 | Heating in DMSO at 100 °C | Heating in DMSO at 150 °C | ||
---|---|---|---|---|---|
Yield of 2, % | Yield of 3, % | Yield of 2, % | Yield of 3, % | ||
1 | 1d | – | – | Decomposition | |
2 | 1e | – | – | Decomposition | |
3 | 1f | 7 | – | 3 | 7 |
4 | 1g | 11 | – | 4 | 7 |
5 | 1h | – | – | Decomposition | |
6 | 1j | 80 | – | – | 78 |
7 | 1k | 82 | – | – | 80 |
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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, 28, 3139. https://doi.org/10.3390/molecules28073139
Ryzhkova YE, Ryzhkov FV, Elinson MN, Vereshchagin AN, Novikov RA, Fakhrutdinov AN. Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines. Molecules. 2023; 28(7):3139. https://doi.org/10.3390/molecules28073139
Chicago/Turabian StyleRyzhkova, Yuliya E., Fedor V. Ryzhkov, Michail N. Elinson, Anatoly N. Vereshchagin, Roman A. Novikov, and Artem N. Fakhrutdinov. 2023. "Thermal Rearrangement of 5-(2-Hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines" Molecules 28, no. 7: 3139. https://doi.org/10.3390/molecules28073139