Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED
Oxidative cyclization is one of the most significant reactions in organic synthesis. Naphthyridine derivatives are often used as luminescence materials in molecular recognition because of their rigid planar structure and as new drugs. Organic light-emitting diodes (OLEDs) have rapidly grown as one o...
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| Format: | Article |
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MDPI AG
2022-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/13/4156 |
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| author | Yuliya E. Ryzhkova Fedor V. Ryzhkov Artem N. Fakhrutdinov Michail N. Elinson |
| author_facet | Yuliya E. Ryzhkova Fedor V. Ryzhkov Artem N. Fakhrutdinov Michail N. Elinson |
| author_sort | Yuliya E. Ryzhkova |
| collection | DOAJ |
| description | Oxidative cyclization is one of the most significant reactions in organic synthesis. Naphthyridine derivatives are often used as luminescence materials in molecular recognition because of their rigid planar structure and as new drugs. Organic light-emitting diodes (OLEDs) have rapidly grown as one of the leading technologies for full-color display panels and eco-friendly lighting sources. In this work, we propose the synthesis of previously unknown benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines via intermolecular oxidative cyclization of 5-(2-hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines in formic acid. The investigation of the reaction mechanism using <sup>1</sup>H-NMR monitoring made it possible to confirm the proposed mechanism of the transformation. The structure of synthesized benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines was confirmed by 2D-NMR spectroscopy. Such a rigid geometry of synthesized compounds is desired to minimize non-radiative energy losses in OLEDs. The quantum chemical calculations are also presented in the study. |
| first_indexed | 2024-03-09T12:43:50Z |
| format | Article |
| id | doaj.art-7a1f0f7de3ae4f3289eb77b77492f742 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T12:43:50Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7a1f0f7de3ae4f3289eb77b77492f7422023-11-30T22:14:32ZengMDPI AGMolecules1420-30492022-06-012713415610.3390/molecules27134156Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LEDYuliya E. Ryzhkova0Fedor V. Ryzhkov1Artem N. Fakhrutdinov2Michail N. Elinson3N. 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, RussiaOxidative cyclization is one of the most significant reactions in organic synthesis. Naphthyridine derivatives are often used as luminescence materials in molecular recognition because of their rigid planar structure and as new drugs. Organic light-emitting diodes (OLEDs) have rapidly grown as one of the leading technologies for full-color display panels and eco-friendly lighting sources. In this work, we propose the synthesis of previously unknown benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines via intermolecular oxidative cyclization of 5-(2-hydroxy-6-oxocyclohexyl)-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines in formic acid. The investigation of the reaction mechanism using <sup>1</sup>H-NMR monitoring made it possible to confirm the proposed mechanism of the transformation. The structure of synthesized benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines was confirmed by 2D-NMR spectroscopy. Such a rigid geometry of synthesized compounds is desired to minimize non-radiative energy losses in OLEDs. The quantum chemical calculations are also presented in the study.https://www.mdpi.com/1420-3049/27/13/4156benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridinechromeno[2,3-<i>b</i>]pyridinecomputer evaluationformic acidNMR studyoxidative cyclization |
| spellingShingle | Yuliya E. Ryzhkova Fedor V. Ryzhkov Artem N. Fakhrutdinov Michail N. Elinson Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED Molecules benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridine chromeno[2,3-<i>b</i>]pyridine computer evaluation formic acid NMR study oxidative cyclization |
| title | Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED |
| title_full | Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED |
| title_fullStr | Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED |
| title_full_unstemmed | Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED |
| title_short | Oxidative Cyclization of 5<i>H</i>-Chromeno[2,3-<i>b</i>]pyridines to Benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridines, Their NMR Study and Computer Evaluation as Material for LED |
| title_sort | oxidative cyclization of 5 i h i chromeno 2 3 i b i pyridines to benzo i b i chromeno 4 3 2 i de i 1 6 naphthyridines their nmr study and computer evaluation as material for led |
| topic | benzo[<i>b</i>]chromeno[4,3,2-<i>de</i>][1,6]naphthyridine chromeno[2,3-<i>b</i>]pyridine computer evaluation formic acid NMR study oxidative cyclization |
| url | https://www.mdpi.com/1420-3049/27/13/4156 |
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