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Molecules 2016, 21(12), 1655; doi:10.3390/molecules21121655

Expedient Organocatalytic Syntheses of 4-Substituted Pyrazolidines and Isoxazolidines

1
Division de Biotechnologie Industrielle, Centre National de Recherche en Biotechnologie, Ali Mendjli Nouvelle Ville, UV 03 BP E73, Constantine 25000, Algeria
2
Laboratoire de Chimie Appliquée, Département de Chimie, Université 8 Mai 1945—Guelma, BP 401, Guelma 24000, Algeria
3
Institute for Molecular Biosciences, The University of Queensland, St. Lucia QLD 4072, Australia
4
Département de Génie de l’Environnement, Faculté de Génie des Procédés, Université de Constantine 3, Ali Mendjli Nouvelle Ville, BP72, Constantine 25000, Algeria
5
Departament de Química Inorgànica i Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, Barcelona 08028, Catalonia, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: Raquel Herrera
Received: 9 November 2016 / Revised: 24 November 2016 / Accepted: 28 November 2016 / Published: 1 December 2016
(This article belongs to the Collection Recent Advances in Organocatalysis)
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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. View Full-Text
Keywords: asymmetric catalysis; isoxazolidinones; pyrazolidinones; organocatalysis; hydrazines; hydroxylamines; enals asymmetric catalysis; isoxazolidinones; pyrazolidinones; organocatalysis; hydrazines; hydroxylamines; enals
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MDPI and ACS Style

Yousfi, T.; Elliott, A.; Hanane, M.; Merdes, R.; Moyano, A. Expedient Organocatalytic Syntheses of 4-Substituted Pyrazolidines and Isoxazolidines. Molecules 2016, 21, 1655.

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