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- Title
Ultrasound-Assisted Synthesis of 3-(Arylamino)-1-ferrocenylpropan-1-ones.
- Authors
Pejović, Anka; Stevanović, Dragana; Damljanović, Ivan; Vukićević, Mirjana; Novaković, Sladjana B.; Bogdanović, Goran A.; Mihajilov-Krstev, Tatjana; Radulović, Niko; Vukićević, Rastko D.
- Abstract
A successful aza- Michael addition of arylamines to a conjugated enone, acryloylferrocene, has been achieved by ultrasonic irradiation of the mixture of these reactants and the catalyst, i.e., montmorillonite K-10. This solvent-free reaction, yielding ferrocene containing Mannich bases, 3-(arylamino)-1-ferrocenylpropan-1-ones, considered as valuable precursors in organic synthesis, has been performed by using a simple ultrasonic cleaner. Among 17 synthesized β-amino ketones, three were new ones, and these were fully characterized by spectroscopic means. X-Ray crystallographic analysis of three of these crystalline products enabled the insight into the conformational details of these compounds. All compounds were evaluated for their antibacterial activities against six Gram-positive and five Gram-negative strains in a microdilution assay. The observed promising antibacterial activity (with a MIC value of 25 μg/ml ( ca. 0.07 μmol/ml) as the best result for almost all tested compounds against Micrococcus flavus) seems not only to be compound but also bacterial species-specific.
- Subjects
AROMATIC amines; IRRADIATION; CATALYSTS; ANTIBACTERIAL agents; ORGANIC synthesis
- Publication
Helvetica Chimica Acta, 2012, Vol 95, Issue 8, p1425
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201200009