Abstract
1-Ferrocenylphenyl-4-aryl(furyl)-2,6-dimethyl-3,5-diethoxycarbonyl-1,4-dihydropyridines and 4-ferrocenyl-2,6-dimethyl-3,5-diethoxycarbonyl-1,4-dihydropyridines (Hantzsch esters) have been prepared, and their reactions with triphenylcarbenium and 1-oxo-2,2,6,6-tetramethyl-piperidinium perchlorate salts have been studied. Treatment with triphenylmethyl perchlorate results in oxidation of the ferrocenyl substituent to the ferrocenium cation, whereas treatment with the oxoammonium cation results in aromatization and the formation of salts containing a pyridinium cation and a neutral ferrocene ring. A 4-ferrocenyl-containing Hantzsch ester which was unsubstituted at the nitrogen atom constituted a single exception to this trend; it could be aromatized only upon treatment with sulfur.
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For Communication 9, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1094–1101, August, 1986.
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Sheinkman, A.K., Nesterova, E.Y., Yashchenko, G.N. et al. Twofold reactivity of 1,2-disubstituted dihydro-n-heteroaromatic systems. 10. Synthesis and aromatization of ferrocene-containing hantzsch esters. Chem Heterocycl Compd 22, 886–893 (1986). https://doi.org/10.1007/BF01175066
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DOI: https://doi.org/10.1007/BF01175066