Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffold
Abstract A new method for the preparation of tetrahydroquinolin-2-one derivatives is presented. This approach involves a two-step reaction between enaminones and acylating agents, immediately followed by electrophilic cyclization, all within a single synthesis procedure, eliminating the need to isol...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2024-01-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-023-50535-0 |
| _version_ | 1797363320828723200 |
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| author | Małgorzata Ryczkowska Alicja Trocka Anna Hromova Sławomir Makowiec |
| author_facet | Małgorzata Ryczkowska Alicja Trocka Anna Hromova Sławomir Makowiec |
| author_sort | Małgorzata Ryczkowska |
| collection | DOAJ |
| description | Abstract A new method for the preparation of tetrahydroquinolin-2-one derivatives is presented. This approach involves a two-step reaction between enaminones and acylating agents, immediately followed by electrophilic cyclization, all within a single synthesis procedure, eliminating the need to isolate intermediates. The entire process is facilitated by the use of acyl Meldrum’s acids which not only shortens the preparation time of the substrates but also easily extends the range of substituents That can be used. The method’s scope and limitations were evaluated with various reagent combinations thus demonstrating its general applicability to the synthesis of tetrahydroquinolin-2-one core. Interestingly, some exceptions to the regular reaction pathway were observed when a strong EDG (electron donating group) was introduced via acyl Meldrum’s acids. The underlying mechanism of this phenomenon was elucidated during the investigation. |
| first_indexed | 2024-03-08T16:19:45Z |
| format | Article |
| id | doaj.art-ae4085ffb5454e56ae3b450b0674622f |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-03-08T16:19:45Z |
| publishDate | 2024-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-ae4085ffb5454e56ae3b450b0674622f2024-01-07T12:26:16ZengNature PortfolioScientific Reports2045-23222024-01-011411910.1038/s41598-023-50535-0Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffoldMałgorzata Ryczkowska0Alicja Trocka1Anna Hromova2Sławomir Makowiec3Department of Organic Chemistry, Faculty of Chemistry, Gdansk University of TechnologyDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of TechnologyDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of TechnologyDepartment of Organic Chemistry, Faculty of Chemistry, Gdansk University of TechnologyAbstract A new method for the preparation of tetrahydroquinolin-2-one derivatives is presented. This approach involves a two-step reaction between enaminones and acylating agents, immediately followed by electrophilic cyclization, all within a single synthesis procedure, eliminating the need to isolate intermediates. The entire process is facilitated by the use of acyl Meldrum’s acids which not only shortens the preparation time of the substrates but also easily extends the range of substituents That can be used. The method’s scope and limitations were evaluated with various reagent combinations thus demonstrating its general applicability to the synthesis of tetrahydroquinolin-2-one core. Interestingly, some exceptions to the regular reaction pathway were observed when a strong EDG (electron donating group) was introduced via acyl Meldrum’s acids. The underlying mechanism of this phenomenon was elucidated during the investigation.https://doi.org/10.1038/s41598-023-50535-0 |
| spellingShingle | Małgorzata Ryczkowska Alicja Trocka Anna Hromova Sławomir Makowiec Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffold Scientific Reports |
| title | Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffold |
| title_full | Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffold |
| title_fullStr | Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffold |
| title_full_unstemmed | Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffold |
| title_short | Meldrum’s acid assisted formation of tetrahydroquinolin-2-one derivatives a short synthetic pathway to the biologically useful scaffold |
| title_sort | meldrum s acid assisted formation of tetrahydroquinolin 2 one derivatives a short synthetic pathway to the biologically useful scaffold |
| url | https://doi.org/10.1038/s41598-023-50535-0 |
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