Molecules 2012, 17(9), 10079-10093; doi:10.3390/molecules170910079
Article

4-Ferrocenylpyridine- and 4-Ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: Multi-Component Synthesis, Structures and Electrochemistry

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Received: 18 July 2012; in revised form: 9 August 2012 / Accepted: 10 August 2012 / Published: 24 August 2012
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The reactions of 2-cyano-3-ferrocenylacrylonitrile (1) with malononitrile (2) in a MeOH/H2O or 2-PrOH/H2O medium in the presence of Na2CO3 afforded 6-alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles 3a,b (multi-component condensation) and 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles 4a,b (multi-component cyclodimerization). Analogous reactions of 1 with 2 in an MeOH/H2O medium in the presence of NaOH, piperidine, or morpholine gave compounds 3a, 4a and 2-amino-4-ferrocenyl-6-hydroxy-, 6-piperidino- and 6-morpholinopyridine-3,5-dicarbonitriles 3ce, respectively. The structures of the compounds 3b, 4a and 4b were established by the spectroscopic data and X-ray diffraction analysis. The electrochemical behaviour of compounds 3b, 3d and 4b was investigated by means of cyclic voltammetry.
Keywords: ferrocene; 2-cyano-3-ferrocenylacrylonitrile; malononitrile; X-ray diffraction; amino(ferrocenyl)pyridine-3,5-dicarbonitriles; cyclic voltammetry
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MDPI and ACS Style

Klimova, E.I.; Flores-Alamo, M.; Maya, S.C.; Martínez, M.E.; Ortiz-Frade, L.; Klimova, T. 4-Ferrocenylpyridine- and 4-Ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: Multi-Component Synthesis, Structures and Electrochemistry. Molecules 2012, 17, 10079-10093.

AMA Style

Klimova EI, Flores-Alamo M, Maya SC, Martínez ME, Ortiz-Frade L, Klimova T. 4-Ferrocenylpyridine- and 4-Ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: Multi-Component Synthesis, Structures and Electrochemistry. Molecules. 2012; 17(9):10079-10093.

Chicago/Turabian Style

Klimova, Elena I.; Flores-Alamo, Marcos; Maya, Sandra Cortez; Martínez, Mark E.; Ortiz-Frade, Luis; Klimova, Tatiana. 2012. "4-Ferrocenylpyridine- and 4-Ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: Multi-Component Synthesis, Structures and Electrochemistry." Molecules 17, no. 9: 10079-10093.


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