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

Authors

  • L. Baumane LOSI
  • A. Krauze LOSI
  • L. Krasnova LOSI
  • S. Belyakov LOSI
  • G. Duburs LOSI
  • J. Stradins LOSI

DOI:

https://doi.org/10.1007/885

Keywords:

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

Abstract

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-tetrahydropyridine-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.

How to Cite
Baumane, L.; Krauze, A.; Krasnova, L.; Belyakov, S.; Duburs, G.; Stradiņš, J. Chem. Heterocycl. Compd. 2014, 49, 1623. [Khim. Geterotsikl. Soedin. 2013, 1752.]

For this article in the English edition see DOI 10.1007/s10593-014-1413-7

Author Biographies

L. Baumane, LOSI

Larisa Baumane

leading researcher

A. Krauze, LOSI

Aivars Krauze

leading researcher

L. Krasnova, LOSI

Laura Krasnova

S. Belyakov, LOSI

Sergey Belyakov

G. Duburs, LOSI

Gunars Duburs

leading researcher, academician

J. Stradins, LOSI

Janis Stradins

leading researcher, academician

Published

2013-10-14

Issue

Section

Original Papers