The synthesis of 2-amino-3-carboxamideindolizines with using pyridinium salt and C-nucleophiles–derivatives acetonitrile
This study reports the synthesis of a pyridinium salt achieved by heating 2-chloropyridine with 2-bromoacetamide in the absence of solvent. The synthesized salt exhibits a high reactivity towards nucleophilic substitution reactions with C-nucleophiles derived from acetonitrile. Furthermore, the resu...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-12-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715624005575 |
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| author | Oleksii Y. Kashner Kyryl O. Bocharov Gennadii E. Khoroshilov |
| author_facet | Oleksii Y. Kashner Kyryl O. Bocharov Gennadii E. Khoroshilov |
| author_sort | Oleksii Y. Kashner |
| collection | DOAJ |
| description | This study reports the synthesis of a pyridinium salt achieved by heating 2-chloropyridine with 2-bromoacetamide in the absence of solvent. The synthesized salt exhibits a high reactivity towards nucleophilic substitution reactions with C-nucleophiles derived from acetonitrile. Furthermore, the resulting N-carboxamide-2(1H)pyridines are efficiently transformed into 2-amino-3-carboxamideindolizines via a cyclisation process, leading to a high yield of the desired product. These findings highlight the potential of this synthetic route for the production of valuable indolizine derivatives. |
| format | Article |
| id | doaj-art-14560bccf6c94200b2f9a19a8d047803 |
| institution | OA Journals |
| issn | 2211-7156 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-14560bccf6c94200b2f9a19a8d0478032025-08-20T02:39:02ZengElsevierResults in Chemistry2211-71562024-12-011210186110.1016/j.rechem.2024.101861The synthesis of 2-amino-3-carboxamideindolizines with using pyridinium salt and C-nucleophiles–derivatives acetonitrileOleksii Y. Kashner0Kyryl O. Bocharov1Gennadii E. Khoroshilov2Luhansk Taras Shevchenko National University, Ivan Bank Street 3, Poltava 36003, UkraineLuhansk Taras Shevchenko National University, Ivan Bank Street 3, Poltava 36003, UkraineCorresponding author.; Luhansk Taras Shevchenko National University, Ivan Bank Street 3, Poltava 36003, UkraineThis study reports the synthesis of a pyridinium salt achieved by heating 2-chloropyridine with 2-bromoacetamide in the absence of solvent. The synthesized salt exhibits a high reactivity towards nucleophilic substitution reactions with C-nucleophiles derived from acetonitrile. Furthermore, the resulting N-carboxamide-2(1H)pyridines are efficiently transformed into 2-amino-3-carboxamideindolizines via a cyclisation process, leading to a high yield of the desired product. These findings highlight the potential of this synthetic route for the production of valuable indolizine derivatives.http://www.sciencedirect.com/science/article/pii/S2211715624005575Pyridinium saltSNVin reactionsIndolizinesCyclisation reactionStereoselectivityThorpe reaction |
| spellingShingle | Oleksii Y. Kashner Kyryl O. Bocharov Gennadii E. Khoroshilov The synthesis of 2-amino-3-carboxamideindolizines with using pyridinium salt and C-nucleophiles–derivatives acetonitrile Results in Chemistry Pyridinium salt SNVin reactions Indolizines Cyclisation reaction Stereoselectivity Thorpe reaction |
| title | The synthesis of 2-amino-3-carboxamideindolizines with using pyridinium salt and C-nucleophiles–derivatives acetonitrile |
| title_full | The synthesis of 2-amino-3-carboxamideindolizines with using pyridinium salt and C-nucleophiles–derivatives acetonitrile |
| title_fullStr | The synthesis of 2-amino-3-carboxamideindolizines with using pyridinium salt and C-nucleophiles–derivatives acetonitrile |
| title_full_unstemmed | The synthesis of 2-amino-3-carboxamideindolizines with using pyridinium salt and C-nucleophiles–derivatives acetonitrile |
| title_short | The synthesis of 2-amino-3-carboxamideindolizines with using pyridinium salt and C-nucleophiles–derivatives acetonitrile |
| title_sort | synthesis of 2 amino 3 carboxamideindolizines with using pyridinium salt and c nucleophiles derivatives acetonitrile |
| topic | Pyridinium salt SNVin reactions Indolizines Cyclisation reaction Stereoselectivity Thorpe reaction |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624005575 |
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