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

Elena I. Klimova, Marcos Flores-Alamo, Sandra Cortez Maya, Mark E. Martínez, Luis Ortiz-Frade, Tatiana Klimova
2012 Molecules  
The reactions of 2-cyano-3-ferrocenylacrylonitrile (1) with malononitrile (2) in a MeOH/H 2 O or 2-PrOH/H 2 O medium in the presence of Na 2 CO 3 afforded 6-alkoxy-2amino-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/H 2 O medium in the presence of NaOH, piperidine, or morpholine gave
more » ... orpholine gave compounds 3a, 4a and 2-amino-4-ferrocenyl-6-hydroxy-, 6-piperidino-and 6-morpholinopyridine-3,5dicarbonitriles 3c-e, 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.
doi:10.3390/molecules170910079 pmid:22922279 fatcat:c4kkwtvsqzb7hddba5ix6sfp3q