4-Ferrocenylpyridine- and 4-ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles: multi-component synthesis, structures and electrochemistry

Molecules. 2012 Aug 24;17(9):10079-93. doi: 10.3390/molecules170910079.

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 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Dihydropyridines / chemical synthesis*
  • Dihydropyridines / chemistry*
  • Electrochemical Techniques
  • Ferrous Compounds / chemical synthesis*
  • Ferrous Compounds / chemistry*
  • Models, Molecular
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry*

Substances

  • Dihydropyridines
  • Ferrous Compounds
  • Nitriles