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Expedient Organocatalytic Syntheses of 4-Substituted Pyrazolidines and Isoxazolidines.


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 ?-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.

SUBMITTER: Yousfi T 

PROVIDER: S-EPMC6274280 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Expedient Organocatalytic Syntheses of 4-Substituted Pyrazolidines and Isoxazolidines.

Yousfi Tarek T   Elliott Alysha A   Hanane Messiad M   Merdes Rachid R   Moyano Albert A  

Molecules (Basel, Switzerland) 20161201 12


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-(<i>n</i>-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 corre  ...[more]

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