A highly chemo- and regioselective synthesis of heterocyclic [3.3.3]propellanes via sequential multicomponent reactions in water
Abstract A simple and highly chemoselective heteroannulation protocol for the synthesis of polysubstituted heterocycles is reported. In this work, various oxa-aza[3.3.3]propellanes were synthesized via a sequential one-pot reaction of ninhydrin, malononitrile and nitroketene acetal or nitroketene am...
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Nature Portfolio
2025-07-01
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| Series: | Scientific Reports |
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| Online Access: | https://doi.org/10.1038/s41598-025-13577-0 |
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| author | Zahra Rahimi Mohammad Bayat Hajar Hosseini |
| author_facet | Zahra Rahimi Mohammad Bayat Hajar Hosseini |
| author_sort | Zahra Rahimi |
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| description | Abstract A simple and highly chemoselective heteroannulation protocol for the synthesis of polysubstituted heterocycles is reported. In this work, various oxa-aza[3.3.3]propellanes were synthesized via a sequential one-pot reaction of ninhydrin, malononitrile and nitroketene acetal or nitroketene aminals in water at ambient temperature. This successive Knoevenagel condensation/Michael addition/cyclization sequence features high atom economy, excellent efficiency, and the use of water as a solvent without the need for metal catalysts or external activators. This method can be presented as a good example of group-assisted purification (GAP), in which traditional purification techniques such as recrystallization and column chromatography are avoided and pure products are obtained simply by washing the crude products. |
| format | Article |
| id | doaj-art-e87bac459d83408fb7dfa0dd8ff5b4e1 |
| institution | Kabale University |
| issn | 2045-2322 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Nature Portfolio |
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| series | Scientific Reports |
| spelling | doaj-art-e87bac459d83408fb7dfa0dd8ff5b4e12025-08-20T04:01:51ZengNature PortfolioScientific Reports2045-23222025-07-0115111110.1038/s41598-025-13577-0A highly chemo- and regioselective synthesis of heterocyclic [3.3.3]propellanes via sequential multicomponent reactions in waterZahra Rahimi0Mohammad Bayat1Hajar Hosseini2Department of Chemistry, Faculty of Science, Imam Khomeini International UniversityDepartment of Chemistry, Faculty of Science, Imam Khomeini International UniversityDepartment of Chemistry, Faculty of Science, Imam Khomeini International UniversityAbstract A simple and highly chemoselective heteroannulation protocol for the synthesis of polysubstituted heterocycles is reported. In this work, various oxa-aza[3.3.3]propellanes were synthesized via a sequential one-pot reaction of ninhydrin, malononitrile and nitroketene acetal or nitroketene aminals in water at ambient temperature. This successive Knoevenagel condensation/Michael addition/cyclization sequence features high atom economy, excellent efficiency, and the use of water as a solvent without the need for metal catalysts or external activators. This method can be presented as a good example of group-assisted purification (GAP), in which traditional purification techniques such as recrystallization and column chromatography are avoided and pure products are obtained simply by washing the crude products.https://doi.org/10.1038/s41598-025-13577-0[3.3.3]propellaneNitroketene aminalMulticomponent reaction |
| spellingShingle | Zahra Rahimi Mohammad Bayat Hajar Hosseini A highly chemo- and regioselective synthesis of heterocyclic [3.3.3]propellanes via sequential multicomponent reactions in water Scientific Reports [3.3.3]propellane Nitroketene aminal Multicomponent reaction |
| title | A highly chemo- and regioselective synthesis of heterocyclic [3.3.3]propellanes via sequential multicomponent reactions in water |
| title_full | A highly chemo- and regioselective synthesis of heterocyclic [3.3.3]propellanes via sequential multicomponent reactions in water |
| title_fullStr | A highly chemo- and regioselective synthesis of heterocyclic [3.3.3]propellanes via sequential multicomponent reactions in water |
| title_full_unstemmed | A highly chemo- and regioselective synthesis of heterocyclic [3.3.3]propellanes via sequential multicomponent reactions in water |
| title_short | A highly chemo- and regioselective synthesis of heterocyclic [3.3.3]propellanes via sequential multicomponent reactions in water |
| title_sort | highly chemo and regioselective synthesis of heterocyclic 3 3 3 propellanes via sequential multicomponent reactions in water |
| topic | [3.3.3]propellane Nitroketene aminal Multicomponent reaction |
| url | https://doi.org/10.1038/s41598-025-13577-0 |
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