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

Abstract

The reactions of 2-cyano-3-ferrocenylacrylonitrile (<strong>1</strong>) with malononitrile (<strong>2</strong>) in a MeOH/H₂O or 2-PrOH/H₂O medium in the presence of Na₂CO₃ afforded 6-alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles <strong>3a</strong>,<strong>b</strong> (multi-component condensation) and 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles <strong>4a</strong>,<strong>b</strong> (multi-component cyclodimerization). Analogous reactions of <strong>1</strong> with <strong>2</strong> in an MeOH/H₂O medium in the presence of NaOH, piperidine, or morpholine gave compounds <strong>3a</strong>, <strong>4a</strong> and 2-amino-4-ferrocenyl-6-hydroxy-, 6-piperidino- and 6-morpholinopyridine-3,5-dicarbonitriles <strong>3c</strong>–<strong>e</strong>, respectively. The structures of the compounds <strong>3b</strong>, <strong>4a</strong> and <strong>4b</strong> were established by the spectroscopic data and X-ray diffraction analysis. The electrochemical behaviour of compounds <strong>3b</strong>, <strong>3d</strong> and <strong>4b</strong> 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