Electrochemical synthesis of substituted 2-amino-4H-chromen-3-carbonitrides based on cross-conjugated dienone derivatives of cyclohexane and malononitrile
The relevance of research in the fi eld of chemistry of compounds of a number of 2-aminochromen(pyran)-3-carbonitrile is due to their practical signifi cance and numerous transformation possibilities. Over the past two decades, there has been a dynamic development of the electrochemical synthesis of...
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Saratov State University
2024-09-01
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| Series: | Известия Саратовского университета. Новая серия: Серия Химия. Биология. Экология |
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| Online Access: | https://ichbe.sgu.ru/sites/ichbe.sgu.ru/files/text-pdf/2024/10/himiya_2024_3-240-248.pdf |
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| author | Nikulin, Alexandr V. Burashnikova, Marina Mihaylovna Vasilkova, Natalia Olegovna Krivenko, Adel P. |
| author_facet | Nikulin, Alexandr V. Burashnikova, Marina Mihaylovna Vasilkova, Natalia Olegovna Krivenko, Adel P. |
| author_sort | Nikulin, Alexandr V. |
| collection | DOAJ |
| description | The relevance of research in the fi eld of chemistry of compounds of a number of 2-aminochromen(pyran)-3-carbonitrile is due to their practical signifi cance and numerous transformation possibilities. Over the past two decades, there has been a dynamic development of the electrochemical synthesis of compounds of this series, which is determined by the possibility of eliminating expensive or toxic reagents, conducting reactions at normal temperatures and pressure in electrolyzers of a fairly simple design and other advantages. Based on the effi ciency and environmental friendliness of this method, we have for the fi rst time synthesized 2-aminotetrahydro-4H-chromene-3-carbonitriles based on available cross-conjugated dienone derivatives of cyclohexane series and malononitrile under electrolysis conditions (platinum cathode, graphite anode, KBr electrolyte, 80% EtOH). The control over the course of the reaction and the electrochemical behavior of all components has been carried out using cyclic voltammetry. The analysis of the voltammograms made it possible to establish the direct activation of the methylene component at the cathode with the formation of the anion - CH(CN)2. A comparison of the electrochemical synthesis of chromencarbonitriles with the chemical one indicates a signifi cant advantage of electrosynthesis due to the exclusion of a toxic organic catalyst, reduction of reaction time with good yields of products, as well as the possibility of monitoring reactions using cyclic voltammetry, dispersion of products. |
| format | Article |
| id | doaj-art-c055ff9c36ec4157ba6ebd0c23907729 |
| institution | OA Journals |
| issn | 1816-9775 2541-8971 |
| language | English |
| publishDate | 2024-09-01 |
| publisher | Saratov State University |
| record_format | Article |
| series | Известия Саратовского университета. Новая серия: Серия Химия. Биология. Экология |
| spelling | doaj-art-c055ff9c36ec4157ba6ebd0c239077292025-08-20T02:35:26ZengSaratov State UniversityИзвестия Саратовского университета. Новая серия: Серия Химия. Биология. Экология1816-97752541-89712024-09-0124324024810.18500/1816-9775-2024-24-3-240-248Electrochemical synthesis of substituted 2-amino-4H-chromen-3-carbonitrides based on cross-conjugated dienone derivatives of cyclohexane and malononitrileNikulin, Alexandr V.0Burashnikova, Marina Mihaylovna1Vasilkova, Natalia Olegovna2Krivenko, Adel P.3Saratov State University, 83, Astrakhanskaya str., Saratov, 410012, RussiaSaratov State University, 83, Astrakhanskaya str., Saratov, 410012, RussiaSaratov State University, 83, Astrakhanskaya str., Saratov, 410012, RussiaSaratov State University, 83, Astrakhanskaya str., Saratov, 410012, RussiaThe relevance of research in the fi eld of chemistry of compounds of a number of 2-aminochromen(pyran)-3-carbonitrile is due to their practical signifi cance and numerous transformation possibilities. Over the past two decades, there has been a dynamic development of the electrochemical synthesis of compounds of this series, which is determined by the possibility of eliminating expensive or toxic reagents, conducting reactions at normal temperatures and pressure in electrolyzers of a fairly simple design and other advantages. Based on the effi ciency and environmental friendliness of this method, we have for the fi rst time synthesized 2-aminotetrahydro-4H-chromene-3-carbonitriles based on available cross-conjugated dienone derivatives of cyclohexane series and malononitrile under electrolysis conditions (platinum cathode, graphite anode, KBr electrolyte, 80% EtOH). The control over the course of the reaction and the electrochemical behavior of all components has been carried out using cyclic voltammetry. The analysis of the voltammograms made it possible to establish the direct activation of the methylene component at the cathode with the formation of the anion - CH(CN)2. A comparison of the electrochemical synthesis of chromencarbonitriles with the chemical one indicates a signifi cant advantage of electrosynthesis due to the exclusion of a toxic organic catalyst, reduction of reaction time with good yields of products, as well as the possibility of monitoring reactions using cyclic voltammetry, dispersion of products.https://ichbe.sgu.ru/sites/ichbe.sgu.ru/files/text-pdf/2024/10/himiya_2024_3-240-248.pdfelectrochemical synthesiscyclic voltammetrydiaryl(getaryl)methylidene cyclohexanonemalononitrile2-aminochromen-3-carbonitrilescondensation |
| spellingShingle | Nikulin, Alexandr V. Burashnikova, Marina Mihaylovna Vasilkova, Natalia Olegovna Krivenko, Adel P. Electrochemical synthesis of substituted 2-amino-4H-chromen-3-carbonitrides based on cross-conjugated dienone derivatives of cyclohexane and malononitrile Известия Саратовского университета. Новая серия: Серия Химия. Биология. Экология electrochemical synthesis cyclic voltammetry diaryl(getaryl)methylidene cyclohexanone malononitrile 2-aminochromen-3-carbonitriles condensation |
| title | Electrochemical synthesis of substituted 2-amino-4H-chromen-3-carbonitrides based on cross-conjugated dienone derivatives of cyclohexane and malononitrile |
| title_full | Electrochemical synthesis of substituted 2-amino-4H-chromen-3-carbonitrides based on cross-conjugated dienone derivatives of cyclohexane and malononitrile |
| title_fullStr | Electrochemical synthesis of substituted 2-amino-4H-chromen-3-carbonitrides based on cross-conjugated dienone derivatives of cyclohexane and malononitrile |
| title_full_unstemmed | Electrochemical synthesis of substituted 2-amino-4H-chromen-3-carbonitrides based on cross-conjugated dienone derivatives of cyclohexane and malononitrile |
| title_short | Electrochemical synthesis of substituted 2-amino-4H-chromen-3-carbonitrides based on cross-conjugated dienone derivatives of cyclohexane and malononitrile |
| title_sort | electrochemical synthesis of substituted 2 amino 4h chromen 3 carbonitrides based on cross conjugated dienone derivatives of cyclohexane and malononitrile |
| topic | electrochemical synthesis cyclic voltammetry diaryl(getaryl)methylidene cyclohexanone malononitrile 2-aminochromen-3-carbonitriles condensation |
| url | https://ichbe.sgu.ru/sites/ichbe.sgu.ru/files/text-pdf/2024/10/himiya_2024_3-240-248.pdf |
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