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Short Paper | Regular issue | Vol 85, No. 10, 2012, pp.2505-2514
Published online, 11th September, 2012
DOI: 10.3987/COM-12-12540
Competitive Condensation and Tandem Cyclization Reactions of 2-Cyano-3-ferrocenylacrylonitrile with Amidines in an Aqueous Medium

Elena I. Klimova,* Marcos Flores-Alamo, José M. Méndez Stivalet, and Tatiana Klimova

*Faculty of Chemistry, National Autonomous University of Mexico, Cd. Universitaria, Coyoacan, C.P. 04510, Mexico

Abstract

The synthesis of a series of ferrocenyl-substituted 2-aminopyridine- and 6-amino-4,5-dihydropyridine-3,5-dicarbonitriles, 4-aminopyrimidine- and 3,4-dihydropyrimidine-5-carbonitriles by reactions of 2-cyano-3-ferrocenylacrylonitrile with amidines in aqueous medium is described. New fused 6-amino-2-ethoxy-4-ferrocenyl-5-ferrocenylmethyl-4,5-dihydropyridine-3,5-dicarbonitrile was prepared in a tricomponent cyclodimerization from 2-cyano-3-ferrocenylacrylonitrile in presence of ethanol. The structures of the obtained compounds were established by IR, 1H and 13C NMR spectroscopy, mass-spectrometry and X-ray diffraction analysis.