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DC Field | Value | Language |
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dc.contributor.author | Yousfi, Tarek | - |
dc.contributor.author | Elliott, Alysha | - |
dc.contributor.author | Hanane, Messiad | - |
dc.contributor.author | Merdes, Rashid | - |
dc.contributor.author | Moyano i Baldoire, Albert | - |
dc.date.accessioned | 2017-03-08T09:42:36Z | - |
dc.date.available | 2017-03-08T09:42:36Z | - |
dc.date.issued | 2016-12-01 | - |
dc.identifier.issn | 1420-3049 | - |
dc.identifier.uri | http://hdl.handle.net/2445/108062 | - |
dc.description.abstract | The efficient organocatalytic synthesis of heterocyclic systems of biological relevance is a subject of growing interest. We have found that the pyrrolidine/benzoic acid-catalyzed reaction of α-substituted propenals such as methacrolein, 2-benzylpropenal and 2-(n-hexyl)propenal with activated hydrazines takes place in very good yields (83%-99.6%) under very mild conditions to afford 4-substituted pyrazolidin-3-ols (as diastereomer mixtures); subsequent oxidation with PCC affords the corresponding-4-substituted-3-pyrazolidinones in essentially quantitative yields. In a similar way, 4-substituted isoxazolidinones are obtained with N-Cbz-hydroxylamine as a reagent. The use of chiral diarylprolinol trimethylsilyl ethers as catalysts allows the synthesis of several of these compounds in optically active form, in some cases with excellent enantioselectivity (up to 96:4 er). A preliminary evaluation of the biological activity shows that some of these compounds exhibit interesting antibacterial and antifungal activities. | - |
dc.format.extent | 16 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | MDPI | - |
dc.relation.isformatof | Reproducció del document publicat a: https://doi.org/10.3390/molecules21121655 | - |
dc.relation.ispartof | Molecules, 2016, vol. 21, p. 1655 | - |
dc.relation.uri | https://doi.org/10.3390/molecules21121655 | - |
dc.rights | cc-by (c) Yousfi, Tarek et al., 2016 | - |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/es | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Catàlisi asimètrica | - |
dc.subject.other | Enantioselective catalysis | - |
dc.title | Expedient organocatalytic syntheses of 4-substituted pyrazolidines and isoxazolidines | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/publishedVersion | - |
dc.identifier.idgrec | 668854 | - |
dc.date.updated | 2017-03-08T09:42:36Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 27916954 | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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668854.pdf | 1.7 MB | Adobe PDF | View/Open |
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