Monatshefte für Chemie / Chemical Monthly

, Volume 112, Issue 8–9, pp 973–985 | Cite as

Synthese und Fluoreszenzeigenschaften von cyansubstituierten 2-Aminopyridinen

Synthesen mit Nitrilen, 61. Mitt.
  • Gerald Koitz
  • Walter Fabian
  • Hans-Werner Schmidt
  • Hans Junek
Organische Chemie und Biochemie

Syntheses with nitriles, LXI. Synthesis and fluorescence of cyano-substituted 2-aminopyridines

Abstract

The synthesis of several 2-aminopyridines is described. The reaction of tetracyanoethylene with 3-imino-propane-carbonitrile gives 2-amino-3,4,5-tricyano-pyridines with alkyl and aryl-substituents, resp., in position 6. Nucleophilic substitution of 2-amino-6-chloro-3,5-dicyanopyridines and 2-amino-6-chloro-3,4,5-tricyano-pyridines with phenolates leads to a variety of pyridines. Spectroscopical data of absorption and fluorescence are presented and the influence of the cyano groups is discussed. The results are in good agreement with quantum chemical calculations (PPP).

Key words

3,5-Dicyanopyridines 3,4,5-Tricyanopyridines 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. 1.
    Schmidt, H. W., Zacharias, G., Junek, H., Synthesis1980, 471.Google Scholar
  2. 2.
    Middleton, W. J., US-Pat. 2,794,803 (1957); C.A.52, 2933 (1958).Google Scholar
  3. 3.
    Little, E. L., Jr., Middleton, W. J., Coffman, D. D., Engelhardt, V. A., Sausen, G. N., J. Amer. Chem. Soc.80, 2832 (1958).Google Scholar
  4. 4.
    Schmidt, H. W., Junek, H., Mh. Chem.108, 895 (1977).Google Scholar
  5. 5.
    Johnson, L. F., Jankowski, W. C., Carbon 13-NMR Spectra, S. 109, New York: Wiley.Google Scholar
  6. 6.
    Levy, G. C., Nelson, G. L., Carbon-13 Nuclear Magnetic Resonance for Organic Chemists. New York: Wiley. 1972.Google Scholar
  7. 7.
    Faganeli, J., Polanc, S., Stanovnik, B., Tiŝler, M., Croat. Chem. Acta48, 161 (1976).Google Scholar
  8. 8.
    Mittelbach, M., Junek, H., Z. Naturforsch.34 b, 1580 (1980).Google Scholar
  9. 9.
    Pariser, R., Parr, R. G., J. Chem. Phys.21, 466 (1953).Google Scholar
  10. 10.
    Pople, J. A., Trans. Faraday Soc.49, 1375 (1953).Google Scholar
  11. 11.
    Fratev, F., Hiebaum, G., Gochev, A., J. Mol. Struct.23, 437 (1974).Google Scholar
  12. 12.
    Fratev, F., Z. Naturforsch.30 a, 1691 (1975).Google Scholar
  13. 13.
    Fratev, F., J. Mol. Struct.30, 217 (1976).Google Scholar
  14. 14.
    Fabian, W., Z. Naturforsch.35 a, 428 (1980).Google Scholar
  15. 15.
    Anliker, R., Müller, G., Fluorescent Whitening Agents. Stuttgart: G. Thieme. 1975.Google Scholar
  16. 16.
    Benary, E., Schwoch, G., Ber. dtsch. chem. Ges.57, 335 (1924).Google Scholar
  17. 17.
    Zacharias G., Dissertation, Universität Graz, 1975.Google Scholar

Copyright information

© Springer-Verlag 1981

Authors and Affiliations

  • Gerald Koitz
    • 1
  • Walter Fabian
    • 1
  • Hans-Werner Schmidt
    • 1
  • Hans Junek
    • 1
  1. 1.Institut für Organische Chemie, Abteilung für Organische Chemie IUniversität GrazGrazÖsterreich

Personalised recommendations