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

Molecules

Elena I. Klimova¹  Marcos Flores-Alamo¹  Sandra Cortez Maya¹  Mark E. Martínez¹  Luis Ortiz-Frade¹ 

[1] ¹Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, C. P. 04510, México D. F., Mexico ²Departamento de Electroquímica, Centro de Investigación y Desarrollo Tecnológico en Electroquímica S.C. Parque Tecnológico Querétaro, Sanfandila, Pedro de Escobedo, C. P. 76703, Querétaro, Mexico

关键词: ferrocene;    2-cyano-3-ferrocenylacrylonitrile;    malononitrile;    X-ray diffraction;    amino(ferrocenyl)pyridine-3;    5-dicarbonitriles;    cyclic voltammetry;   

DOI  :  10.3390/molecules170910079

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.