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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 11, pp 1623–1630 | Cite as

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

  • L. BaumaneEmail author
  • A. Krauze
  • L. Krasnova
  • S. Belyakov
  • G. Duburs
  • J. Stradiņš
Article

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.

Keywords

6-alkylsulfanyl-5-cyano-2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylates electro-chemical oxidation hydrogen bonding X-ray diffraction analysis 

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • L. Baumane
    • 1
    Email author
  • A. Krauze
    • 1
  • L. Krasnova
    • 1
  • S. Belyakov
    • 1
  • G. Duburs
    • 1
  • J. Stradiņš
    • 1
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia

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