Oxidative Cyclization of 5H-Chromeno[2,3-b]pyridines to Benzo[b]chromeno[4,3,2-de][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED
Abstract
:1. Introduction
2. Results and Discussion
2.1. Intramolecular Oxidative Cyclization of 5H-Chromeno[2,3-b]pyridines to Benzo[b]chromeno[4,3,2-de][1,6]naphthyridines
2.2. 2D NMR Study of the Structure of Compound 2a
2.3. 1H NMR Reaction Monitoring and Mechanism of the Process
2.4. Computer Evaluation as Material for LED
3. Materials and Methods
3.1. General Information
3.2. Intramolecular Oxidative Cyclization of 5-(2-Hydroxy-6-Oxocyclohexyl)-5H-Chromeno[2,3-b]pyridine-3-Carbonitrile 1
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 | Catalyst | Time (h) | Temp. (°C) | Yield (%) |
---|---|---|---|---|---|
1 | EtOH | TsOH × H2O | 2 | 78 | – |
2 | EtOH | HCl | 2 | 78 | – |
3 | EtOH | P2O5 | 2 | 78 | – |
4 | HCOOH | – | 2 | 101 | 78 2 |
5 | HCONH2 | – | 2 | 100 | 54 2 |
6 | HCONH2 | – | 4 | 100 | 58 2 |
7 | HCONH2 | – | 2 | 210 | 31 |
8 | HCOOH | – | 4 | 101 | 79 2 |
9 | HCOOH | – | 6 | 101 | 81 |
Compound | Total Energy, a.u. | E(HOMO), eV | E(LUMO), eV | ∆E(L-H), eV |
---|---|---|---|---|
2a | −1183.31 | −5.789 | −1.670 | 4.119 |
2b | −1298.58 | −5.692 | −1.551 | 4.142 |
2c | −3755.00 | −5.751 | −1.675 | 4.076 |
2d | −6326.70 | −5.715 | −1.645 | 4.071 |
2e | −3869.55 | −5.564 | −1.556 | 4.008 |
2f | −1104.56 | −5.785 | −1.653 | 4.132 |
Compound | HOMO | LUMO |
---|---|---|
2a | ||
2b | ||
2c | ||
2d | ||
2e | ||
2f |
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Ryzhkova, Y.E.; Ryzhkov, F.V.; Fakhrutdinov, A.N.; Elinson, M.N. Oxidative Cyclization of 5H-Chromeno[2,3-b]pyridines to Benzo[b]chromeno[4,3,2-de][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED. Molecules 2022, 27, 4156. https://doi.org/10.3390/molecules27134156
Ryzhkova YE, Ryzhkov FV, Fakhrutdinov AN, Elinson MN. Oxidative Cyclization of 5H-Chromeno[2,3-b]pyridines to Benzo[b]chromeno[4,3,2-de][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED. Molecules. 2022; 27(13):4156. https://doi.org/10.3390/molecules27134156
Chicago/Turabian StyleRyzhkova, Yuliya E., Fedor V. Ryzhkov, Artem N. Fakhrutdinov, and Michail N. Elinson. 2022. "Oxidative Cyclization of 5H-Chromeno[2,3-b]pyridines to Benzo[b]chromeno[4,3,2-de][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED" Molecules 27, no. 13: 4156. https://doi.org/10.3390/molecules27134156