Please use this identifier to cite or link to this item:
http://hdl.handle.net/2445/108062
Title: | Expedient organocatalytic syntheses of 4-substituted pyrazolidines and isoxazolidines |
Author: | Yousfi, Tarek Elliott, Alysha Hanane, Messiad Merdes, Rashid Moyano i Baldoire, Albert |
Keywords: | Catàlisi asimètrica Enantioselective catalysis |
Issue Date: | 1-Dec-2016 |
Publisher: | MDPI |
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. |
Note: | Reproducció del document publicat a: https://doi.org/10.3390/molecules21121655 |
It is part of: | Molecules, 2016, vol. 21, p. 1655 |
URI: | http://hdl.handle.net/2445/108062 |
Related resource: | https://doi.org/10.3390/molecules21121655 |
ISSN: | 1420-3049 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
668854.pdf | 1.7 MB | Adobe PDF | View/Open |
This item is licensed under a Creative Commons License