Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation
The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino-2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that...
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MDPI AG
2021-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/16/4719 |
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| author | Daniil N. Lyapustin Evgeny N. Ulomsky Ilya A. Balyakin Alexander V. Shchepochkin Vladimir L. Rusinov Oleg N. Chupakhin |
| author_facet | Daniil N. Lyapustin Evgeny N. Ulomsky Ilya A. Balyakin Alexander V. Shchepochkin Vladimir L. Rusinov Oleg N. Chupakhin |
| author_sort | Daniil N. Lyapustin |
| collection | DOAJ |
| description | The reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino-2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed. |
| first_indexed | 2024-03-10T08:34:26Z |
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| id | doaj.art-aca4eb4075f54e528780b6d96c0f20ad |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T08:34:26Z |
| publishDate | 2021-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-aca4eb4075f54e528780b6d96c0f20ad2023-11-22T08:50:56ZengMDPI AGMolecules1420-30492021-08-012616471910.3390/molecules26164719Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental SubstantiationDaniil N. Lyapustin0Evgeny N. Ulomsky1Ilya A. Balyakin2Alexander V. Shchepochkin3Vladimir L. Rusinov4Oleg N. Chupakhin5Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaNANOTECH Centre, Ural Federal University, 620002 Ekaterinburg, RussiaInstitute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, 620041 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, RussiaThe reaction tolerance of the multicomponent process between 3-aminoazoles, 1-morpholino-2-nitroalkenes, and aldehydes was studied. The main patterns of this reaction have been established. Conditions for the oxidation of 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines were selected. Previous claims that the 4,7-dihydro-6-nitroazolo[1,5-a]pyrimidines could not be aromatised have now been refuted. Compounds with an electron-donor substituent at position seven undergo decomposition during oxidation. The phenomenon was explained based on experimental data, electro-chemical experiment, and quantum-chemical calculation. The mechanism of oxidative degradation has been proposed.https://www.mdpi.com/1420-3049/26/16/4719azolo[1,5-a]pyrimidinesnitro-synthonsoxidationoxidative destructionsynthesis of heterocyclesmulticomponent reactions |
| spellingShingle | Daniil N. Lyapustin Evgeny N. Ulomsky Ilya A. Balyakin Alexander V. Shchepochkin Vladimir L. Rusinov Oleg N. Chupakhin Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation Molecules azolo[1,5-a]pyrimidines nitro-synthons oxidation oxidative destruction synthesis of heterocycles multicomponent reactions |
| title | Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation |
| title_full | Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation |
| title_fullStr | Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation |
| title_full_unstemmed | Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation |
| title_short | Oxidative Aromatization of 4,7-Dihydro-6-nitroazolo[1,5-a]pyrimidines: Synthetic Possibilities and Limitations, Mechanism of Destruction, and the Theoretical and Experimental Substantiation |
| title_sort | oxidative aromatization of 4 7 dihydro 6 nitroazolo 1 5 a pyrimidines synthetic possibilities and limitations mechanism of destruction and the theoretical and experimental substantiation |
| topic | azolo[1,5-a]pyrimidines nitro-synthons oxidation oxidative destruction synthesis of heterocycles multicomponent reactions |
| url | https://www.mdpi.com/1420-3049/26/16/4719 |
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