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Issue 11, 2016
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Synthesis of ferrocene amides and esters from aminoferrocene and 2-substituted ferrocenecarboxylic acid and properties thereof

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Abstract

Different ferrocenecarboxamides were synthesized from aminoferrocene and various acid coupling partners such as Nα-Boc-L-tryptophan and N-protected sugar amino acids (N-Boc-3-amino-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranoic acid, N-Boc-3-amino-3-deoxy-1,2-O-isopropylidene-α-D-xylofuranoic acid and their corresponding homo- and hetero-dimers). Similarly, reactions between 2-aminoethyl ferrocenecarboxylate and N-protected sugar amino acids afforded compounds with a carboxamide functional group remotely positioned from the ferrocene core. The X-ray diffraction structure of one of them showed the presence of an intermolecular hydrogen bond between the amide functional groups. Carbonylamino (or carbonyloxy) and oxycarbonyl 1,2-disubstituted ferrocenes were prepared either as racemic mixtures or in enantiomerically pure (SP) form. Their electrochemical evaluation revealed distinctive features. Interestingly, the enantiomerically pure ferrocene diester showed a large potential shift (+45 mV) in the presence of L-glutamic acid. Finally, some of the synthesized ferrocenes were evaluated for their antibacterial, antifungal and antiproliferative (MCF-7) activities.

Graphical abstract: Synthesis of ferrocene amides and esters from aminoferrocene and 2-substituted ferrocenecarboxylic acid and properties thereof

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Publication details

The article was received on 28 Jun 2016, accepted on 21 Sep 2016 and first published on 22 Sep 2016


Article type: Paper
DOI: 10.1039/C6NJ02018F
Citation: New J. Chem., 2016,40, 9441-9447
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    Synthesis of ferrocene amides and esters from aminoferrocene and 2-substituted ferrocenecarboxylic acid and properties thereof

    P. Srinivas, S. Prabhakar, F. Chevallier, E. Nassar, W. Erb, V. Dorcet, V. Jouikov, P. Radha Krishna and F. Mongin, New J. Chem., 2016, 40, 9441
    DOI: 10.1039/C6NJ02018F

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