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Molecules 2016, 21(11), 1472; doi:10.3390/molecules21111472

Practical and Metal-Free Synthesis of Novel Enantiopure Amides Containing the Potentially Bioactive 5-Nitroimidazole Moiety

Aix-Marseille Université, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS 30064, 13385 Marseille CEDEX 05, France
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Academic Editor: Wim Dehaen
Received: 30 September 2016 / Revised: 26 October 2016 / Accepted: 28 October 2016 / Published: 4 November 2016
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

We report here a practical and metal-free synthesis of novel enantiopure amides containing the drug-like 5-nitroimidazole scaffold. The first step was a metal-free diastereoselective addition of 4-(4-(chloromethyl)phenyl)-1,2-dimethyl-5-nitro-1H-imidazole to enantiomerically pure N-tert-butanesulfinimine. Then, the N-tert-butanesulfinyl–protected amine was easily deprotected under acidic conditions. Finally, the primary amine was coupled with different acid chlorides or acids to give the corresponding amides. The mild reaction conditions and high tolerance for various substitutions make this approach attractive for constructing pharmacologically interesting 5-nitroimidazoles. View Full-Text
Keywords: 5-nitroimidazoles; metal-free; amides 5-nitroimidazoles; metal-free; amides
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Spitz, C.; Mathias, F.; Giuglio-Tonolo, A.G.; Terme, T.; Vanelle, P. Practical and Metal-Free Synthesis of Novel Enantiopure Amides Containing the Potentially Bioactive 5-Nitroimidazole Moiety. Molecules 2016, 21, 1472.

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