Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction
The simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of <i>S</i>-vinyl phosphorodithioate with thi...
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MDPI AG
2021-03-01
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| Online Access: | https://www.mdpi.com/1996-1944/14/6/1342 |
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| author | Bartosz Jędrzejewski Mateusz Musiejuk Justyna Doroszuk Dariusz Witt |
| author_facet | Bartosz Jędrzejewski Mateusz Musiejuk Justyna Doroszuk Dariusz Witt |
| author_sort | Bartosz Jędrzejewski |
| collection | DOAJ |
| description | The simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of <i>S</i>-vinyl phosphorodithioate with thiotosylates or <i>S</i>-vinyl thiotosylate with thiols. The designed methods allow for the synthesis of unsymmetrical vinyl disulfides with additional functionalities such as hydroxy, carboxy, protected amino, or ester groups. Vinyl disulfides reacted with the generated transient <i>o</i>-iminothioquinones in an inverse electron-demand [4+2] cycloaddition to produce benzo[<i>b</i>][1,4]thiazine derivatives. |
| first_indexed | 2024-03-10T13:22:09Z |
| format | Article |
| id | doaj.art-46393888709845ecb0eae28c82f500ef |
| institution | Directory Open Access Journal |
| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-10T13:22:09Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Materials |
| spelling | doaj.art-46393888709845ecb0eae28c82f500ef2023-11-21T09:57:07ZengMDPI AGMaterials1996-19442021-03-01146134210.3390/ma14061342Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder ReactionBartosz Jędrzejewski0Mateusz Musiejuk1Justyna Doroszuk2Dariusz Witt3Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, PolandDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, PolandThe simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of <i>S</i>-vinyl phosphorodithioate with thiotosylates or <i>S</i>-vinyl thiotosylate with thiols. The designed methods allow for the synthesis of unsymmetrical vinyl disulfides with additional functionalities such as hydroxy, carboxy, protected amino, or ester groups. Vinyl disulfides reacted with the generated transient <i>o</i>-iminothioquinones in an inverse electron-demand [4+2] cycloaddition to produce benzo[<i>b</i>][1,4]thiazine derivatives.https://www.mdpi.com/1996-1944/14/6/1342alkenescycloadditionhetero-Diels-Alderthiosulfonatesvinyl disulfides |
| spellingShingle | Bartosz Jędrzejewski Mateusz Musiejuk Justyna Doroszuk Dariusz Witt Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction Materials alkenes cycloaddition hetero-Diels-Alder thiosulfonates vinyl disulfides |
| title | Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction |
| title_full | Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction |
| title_fullStr | Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction |
| title_full_unstemmed | Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction |
| title_short | Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction |
| title_sort | convenient synthesis of functionalized unsymmetrical vinyl disulfides and their inverse electron demand hetero diels alder reaction |
| topic | alkenes cycloaddition hetero-Diels-Alder thiosulfonates vinyl disulfides |
| url | https://www.mdpi.com/1996-1944/14/6/1342 |
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