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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

1,* , 1
,
1
,
1
,
2
 and
1
1 Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, C. P. 04510, México D. F., Mexico 2 Departamento de Electroquímica, Centro de Investigación y Desarrollo Tecnológico en Electroquímica S.C. Parque Tecnológico Querétaro, Sanfandila, Pedro de Escobedo, C. P. 76703, Querétaro, Mexico
* Author to whom correspondence should be addressed.
Received: 18 July 2012 / Revised: 9 August 2012 / Accepted: 10 August 2012 / Published: 24 August 2012
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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 ferrocene; 2-cyano-3-ferrocenylacrylonitrile; malononitrile; X-ray diffraction; amino(ferrocenyl)pyridine-3,5-dicarbonitriles; cyclic voltammetry
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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.

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