Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles
Due to the presence of two acrylonitrile fragments, 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles are prone to react under Radziszewski reaction conditions (oxidative hydrolysis of nitriles to amides) with the simultaneous epoxidation and formation of epoxyamides. We found that the reaction proceeds in a...
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MDPI AG
2022-10-01
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| Series: | Chemistry Proceedings |
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| Online Access: | https://www.mdpi.com/2673-4583/8/1/111 |
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| author | Polina G. Dahno Arina G. Levchenko Victor V. Dotsenko |
| author_facet | Polina G. Dahno Arina G. Levchenko Victor V. Dotsenko |
| author_sort | Polina G. Dahno |
| collection | DOAJ |
| description | Due to the presence of two acrylonitrile fragments, 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles are prone to react under Radziszewski reaction conditions (oxidative hydrolysis of nitriles to amides) with the simultaneous epoxidation and formation of epoxyamides. We found that the reaction proceeds in a non-selective way and yields a mixture of products of regioisomeric oxidation. Only in one case we succeeded to isolate the product of double epoxidation. The structure of the epoxyamides products was confirmed by IR and NMR spectroscopy data. |
| first_indexed | 2024-03-11T06:45:46Z |
| format | Article |
| id | doaj.art-806b8b8ed9d9458db75e37a59f636aba |
| institution | Directory Open Access Journal |
| issn | 2673-4583 |
| language | English |
| last_indexed | 2024-03-11T06:45:46Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
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| series | Chemistry Proceedings |
| spelling | doaj.art-806b8b8ed9d9458db75e37a59f636aba2023-11-17T10:19:37ZengMDPI AGChemistry Proceedings2673-45832022-10-018111110.3390/ecsoc-25-11790Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazolesPolina G. Dahno0Arina G. Levchenko1Victor V. Dotsenko2Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya Str., 350040 Krasnodar, RussiaDepartment of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya Str., 350040 Krasnodar, RussiaDepartment of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya Str., 350040 Krasnodar, RussiaDue to the presence of two acrylonitrile fragments, 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles are prone to react under Radziszewski reaction conditions (oxidative hydrolysis of nitriles to amides) with the simultaneous epoxidation and formation of epoxyamides. We found that the reaction proceeds in a non-selective way and yields a mixture of products of regioisomeric oxidation. Only in one case we succeeded to isolate the product of double epoxidation. The structure of the epoxyamides products was confirmed by IR and NMR spectroscopy data.https://www.mdpi.com/2673-4583/8/1/111arylmethylene cyanothioacetamides1,2,4-thiadiazolesRadziszewski oxidationepoxyamides |
| spellingShingle | Polina G. Dahno Arina G. Levchenko Victor V. Dotsenko Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles Chemistry Proceedings arylmethylene cyanothioacetamides 1,2,4-thiadiazoles Radziszewski oxidation epoxyamides |
| title | Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles |
| title_full | Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles |
| title_fullStr | Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles |
| title_full_unstemmed | Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles |
| title_short | Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles |
| title_sort | radziszewski type oxidation of 3 5 di α cyanostyryl 1 2 4 thiadiazoles |
| topic | arylmethylene cyanothioacetamides 1,2,4-thiadiazoles Radziszewski oxidation epoxyamides |
| url | https://www.mdpi.com/2673-4583/8/1/111 |
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