6-Alkylsulfanyl-5-cyano-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylates containing electron-donating or electron-withdrawing groups were prepared by alkylation of 6-thioxo-1,4,5,6-tetra-hydropyridine-3-carboxylate with alkyl halides. The H-bond formation in the case of 6-alkylsulfanyl substituent bearing sterically small hydrogen bond acceptor explains a partial lack of correlation of the electrochemical oxidation potentials with Taft's σ*-constants.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1752-1759, November, 2013.
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Baumane, L., Krauze, A., Krasnova, L. et al. Role of Steric Factors in Intramolecular H-Bond Formation and Peculiarities of Electrochemical Oxidation of Ethyl 6-Alkylsulfanyl-5-Cyano-2-Methyl-4-Phenyl-1,4-Dihydropyridine-3-Carboxylates. Chem Heterocycl Comp 49, 1623–1630 (2014). https://doi.org/10.1007/s10593-014-1413-7
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DOI: https://doi.org/10.1007/s10593-014-1413-7