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

Cédric Spitz (1) , Fanny Mathias (1) , Alain Gamal Giuglio-Tonolo (1) , Thierry Terme (1) , Patrice Vanelle (1)

1 ICR - Institut de Chimie Radicalaire

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.

Mots clés: 5-nitroimidazoles; metal-free; amides

Domaines: Chimie

Cédric Spitz, Fanny Mathias, Alain Gamal Giuglio-Tonolo, Thierry Terme, Patrice Vanelle. Practical and Metal-Free Synthesis of Novel Enantiopure Amides Containing the Potentially Bioactive 5-Nitroimidazole Moiety. Molecules, 2016, ⟨10.3390/molecules21111472⟩. ⟨hal-01425650⟩