Article Dans Une Revue Journal of Fluorine Chemistry Année : 2011

ClickEnam. 1. Synthesis of novel 1,4-disubsituted-[1,2,3]-triazole-derived β-aminovinyl trifluoromethylated ketones and their copper(II) complexes

Résumé

The copper(I) catalyzed cycloaddition reaction of N-Boc propargyl amine (dipolarophile) 1 with benzyl azide (1,3-dipole) 2 was found to proceed smoothly in t-BuOH/H2O at room temperature, to furnish the corresponding 1,4-disubstituted-[1,2,3]-triazole-derived N-Boc amine 3 in good yield. Deprotection of 3 with trifluoroacetic acid and addition of the trifluoroacetate salt 4 in the presence of triethylamine, with a series of methoxyvinyl(trifluoromethyl)ketones 10–14, gave the corresponding β-aminovinyl trifluoromethylated ketones 15–19 in moderate to good yields. Two copper(II) complexes, one monomer and one dimer with chlorine double bridge, 20 and 21, respectively, were also prepared and their crystal structure determined. β-Aminovinyl trifluoromethylated ketones 15–17 and complexes 20 and 21 have been screened as potential antifungal agents and the antimalarial activity of 15 and 16 were tested against two Plasmodium falciparum strains (3D7 and W2).

DOI

Cite 10.5517/ccwhtms Jeu de données Chopin, N., Decamps, S., Gouger, A., Medebielle, M., Picot, S., Bienvenu, A.-L., & Pilet, G. (2011). CCDC 819566: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCWHTMS

DOI

Cite 10.5517/ccwhtlr Jeu de données Chopin, N., Decamps, S., Gouger, A., Medebielle, M., Picot, S., Bienvenu, A.-L., & Pilet, G. (2011). CCDC 819565: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCWHTLR

Dates et versions

hal-02907163 , version 1 (27-07-2020)

Identifiants

Citer

Nicolas Chopin, Sophie Decamps, Aude Gouger, Maurice Médebielle, Stéphane Picot, et al.. ClickEnam. 1. Synthesis of novel 1,4-disubsituted-[1,2,3]-triazole-derived β-aminovinyl trifluoromethylated ketones and their copper(II) complexes. Journal of Fluorine Chemistry, 2011, 132 (10), pp.850-857. ⟨10.1016/j.jfluchem.2011.05.011⟩. ⟨hal-02907163⟩
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