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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 11, pp 1640–1652 | Cite as

Electron Transfer Reactions in the Chemistry of Di- and Tetrahydropyridines

  • B. TurovskaEmail author
  • I. Goba
  • A. Lielpetere
  • I. Turovskis
  • V. Lusis
  • Dz. Muceniece
  • J. Stradiņš
Article

The mechanism of electrochemical oxidation of 1,2,3,4-tetrahydropyridines in acetonitrile has been studied. A single reversible one-electron oxidation is registered in the accessible voltage range. The reversibility of the process is sensitive to the traces of oxygen in solution. The electrochemically generated radical cation of tetrahydropyridine may act as a mediator in an indirect oxidation of dihydropyridines if the difference in oxidation potentials between two compounds is less than 200 mV. During the indirect oxidation of 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester to 3,5-bis(ethoxycarbonyl)-2,4,6-trimethylpyridinium perchlorate, some of the starting tetrahydropyridine is protonated, thus making it anodically inactive.

Keywords

1,4-dihydropyridine 1,2,3,4-tetrahydropyridine charge transfer mediator electrooxidation indirect oxidation 

Notes

The work was financially supported by the Latvian Council of Science (grant 09-1558) and by the European Regional Development Fund (ERDF) project No. 2DP/2.1.1.1.0/10/APIA/VIAA/065.

The authors thank Dr. Chem. E. Liepinsh for NMR analysis of epimers on the Bruker DMX-600 spectrometer and Dr. Chem. S. Grinberga for GC-MS analysis.

References

  1. 1.
    P. Molina, A. Pastor, and M. J. Vilaplana, J. Org. Chem., 61, 8094 (1996).CrossRefGoogle Scholar
  2. 2.
    L. M. Sayre, P. K. Arora, S. C. Feke, and F. L. Urbach, J. Am. Chem. Soc., 108, 2464 (1986).CrossRefGoogle Scholar
  3. 3.
    T. Shono, in: Z. Rappoport (editor), The Chemistry of Enamines, Wiley (1994).Google Scholar
  4. 4.
    V. D. Parker, Acta Chem. Scand., 52, 145 (1998).CrossRefGoogle Scholar
  5. 5.
    W. J. Albery and S. Bruckenstein, Trans. Faraday Soc., 62, 1920 (1966).CrossRefGoogle Scholar
  6. 6.
    J. Ogle, J. Stradins, and L. Baumane, Electrochim. Acta, 39, 73 (1994).CrossRefGoogle Scholar
  7. 7.
    A. Anne, P. Hapiot, J. Moiroux, P. Neta, and J. M. Saveant, J. Am. Chem. Soc., 114, 4694 (1992).CrossRefGoogle Scholar
  8. 8.
    J. Ludvik, J. Volke, and J. Klima, Electrochim. Acta, 32, 1063 (1987).CrossRefGoogle Scholar
  9. 9.
    H. R. Memarian, M. Ghazaie, and S. K. Mehneh, Z. Naturforsch., B: J. Chem. Sci., 64b, 1187 (2009).Google Scholar
  10. 10.
    B. Turovska, I. Goba, I. Turovskis, S. Grinberga, S. Belyakov, S. Stupnikova, E. Liepinsh, and J. Stradins, Khim. Geterotsikl. Soedin., 1829 (2008). [Chem. Heterocycl. Compd., 44, 1483 (2008).]Google Scholar
  11. 11.
    J. Stradins, J. Ogle, V. Kadysh, L. Baumane, R. Gavars, and G. Duburs, J. Electroanal. Chem., 226, 103 (1987).CrossRefGoogle Scholar
  12. 12.
    K. Daasbjerg, S. U. Pedersen, and H. Lund, Acta Chem. Scand., 45, 424 (1991).CrossRefGoogle Scholar
  13. 13.
    L. V. Jorgensen and H. Lund, Acta Chem. Scand., 48, 759 (1994).CrossRefGoogle Scholar
  14. 14.
    L. Eberson, Acta Chem. Scand., 53, 751 (1999).CrossRefGoogle Scholar
  15. 15.
    K. Broka and J. Stradins, Latv. J. Chem., 2, 245 (1993).Google Scholar
  16. 16.
    R. G. Pearson, J. Am. Chem. Soc., 108, 6109 (1986).CrossRefGoogle Scholar
  17. 17.
    J. F. Evans and H. N. Blount, J. Am. Chem. Soc., 100, 4191 (1978).CrossRefGoogle Scholar
  18. 18.
    U. Rosentreter, Synthesis, 210 (1985).Google Scholar
  19. 19.
    D. Kh. Mutsenietse, V. K. Lusis, and G. Ya. Duburs, Khim. Geterotsikl. Soedin., 1225 (1982). [Chem. Heterocycl. Compd., 18, 942 (1982).]Google Scholar
  20. 20.
    J. R. Pfister, Synthesis, 689 (1990).Google Scholar
  21. 21.
    B. Loev, M. M. Goodman, K. M. Snader, R. Tedeschi, and E. Macko, J. Med. Chem. 17, 956 (1974).CrossRefGoogle Scholar
  22. 22.
    X. Wang, H. Gong, Z. Quan, L. Li, and H. Ye, Synth. Commun., 41, 3251 (2011).CrossRefGoogle Scholar
  23. 23.
    A. A. Krauze, E. E. Liepinsh, Z. A. Kalme, Yu. E. Pelchers, and G. Ya. Duburs, Khim. Geterotsikl. Soedin., 1504 (1984). [Chem. Heterocycl. Compd., 20, 1241 (1984).]Google Scholar
  24. 24.
    M. Anniyappan, D. Muralidharan, and P. T. Perumal, Tetrahedron, 58, 5069 (2002).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • B. Turovska
    • 1
    Email author
  • I. Goba
    • 1
  • A. Lielpetere
    • 1
  • I. Turovskis
    • 1
  • V. Lusis
    • 1
  • Dz. Muceniece
    • 1
  • J. Stradiņš
    • 1
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia

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