COMPETITIVE CONDENSATION AND TANDEM CYCLIZATION REACTIONS OF 2-CYANO-3-FERROCENYLACRYLONITRILE WITH AMIDINES IN AN AQUEOUS MEDIUM

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-e...

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Bibliographic Details
Published inHeterocycles Vol. 85; no. 10; pp. 2505 - 2515
Main Authors Klimova, Elena I., Flores-Alamo, Marcos, Mendez Stivalet, Jose M., Klimova, Tatiana
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EFFICIENT SYNTHESIS
2-Cyano-3-ferrocenylacrylonitrile Ferrocenyl(pyridine)dicarbonitrile Ferrocenyl(pyrimidine)carbonitrile
PYRIMIDINE-DERIVATIVES
BIOORGANOMETALLIC CHEMISTRY
Cyclodimerization
Ferrocene
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Summary: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-ferroceny1-5-ferrocenylmethyl-5-ferrocenyl methyl-4,5dihydropyridine-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, H-1 and C-13 NMR spectroscopy, mass-spectrometry and X-ray diffraction analysis.
ISSN:0385-5414
DOI:10.3987/COM-12-12540