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Monatshefte für Chemie / Chemical Monthly

, Volume 122, Issue 12, pp 1055–1061 | Cite as

Pyridazines, LVIII: 1-Phenyl-1-pyridazinyl-2-substituted ethenes, synthesis and configuration

  • Gottfried Heinisch
  • Wolfgang Holzer
  • Thierry Huber
Organische Chemie Und Biochemie

Summary

Starting from phenyl pyridazinyl ketones1 and3 various 1-phenyl-1-pyridazinyl-2-substituted ethenes (2 a–c, 4, 5 a, b, 6 a, b, 7–9) were prepared by Wittig-Horner- oder Wittig-type reactions. Configurational assignments of these novel compounds were achieved by NOE difference spectroscopy.

Keywords

Phenyl-4-pyridazinylmethanone Phenyl-3-pyridazinylmethanone Phenyl-pyridazinyl-ethenes configuration of NOE-difference spectroscopy 

Pyridazine, 58. Mitt.: Neue 2-substituierte 1-Phenyl-1-pyridazinylethene, Synthese und Konfiguration

Zusammenfassung

Aus den Phenyl-pyridazinylketonen1 und3 wurden mittels Wittig-Horner- bzw. Wittig-Reaktion die 2-substituierten Phenyl-pyridazinylethene2 a–c, 4, 5 a, b, 6 a, b, 7–9 dargestellt. Die Aufklärung der Konfiguration dieser neuen Verbindungen erfolgte mittels NOE-Differenzspektroskopie.

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References

  1. [1]
    Pyridazines, 57: Haider N., Heinisch G., Moshuber J. (submitted) Arch. Pharm. (Weinheim)Google Scholar
  2. [2]
    Taken in part from the Ph.D.-Thesis of T. H., University of Vienna, 1991Google Scholar
  3. [3]
    Lundström J., Högberg T., Gosztonyi T., de Paulis T. (1981) Arzneim.-Forsch./Drug Res.31: 486Google Scholar
  4. [4]
    Högberg T., Ross S. B., Ström P., Grunewald G. L., Creese M. W., Bunce J. D. (1988) J. Med. Chem.31: 913Google Scholar
  5. [5]
    Drugs of the Future (1985)10: 548, and references cited thereinGoogle Scholar
  6. [6]
    Drugs of the Future (1986)11: 183, and references cited thereinGoogle Scholar
  7. [7]
    Drug Data Report (1985)7: 363, and references cited thereinGoogle Scholar
  8. [8]
    Drug Data Report (1985)7: 106, and references cited thereinGoogle Scholar
  9. [9]
    Haider N., Heinisch G., Offenberger S. (1989) Pharmazie44: 598Google Scholar
  10. [10]
    Easmon J., Heinisch G., Holzer W., Rosenwirth B. (1989) Arzneim.-Forsch./Drug Res.39 (II): 1196Google Scholar
  11. [11]
    A preliminary anticonvulsant screening of phenyl 4-pyridazinyl ketone indicated an improved activity compared to that of the 3- and 4-pyridyl congeners [12]Google Scholar
  12. [12]
    Breen M. P., Bojanowski E. M., Cipolle R. J., Dunn III W. J., Frank E., Gearien J. E. J. (1973) Pharm. Sci.62: 847Google Scholar
  13. [13]
    Heinisch G., Kirchner I. (1979) Monatsh. Chem.110: 365Google Scholar
  14. [14]
    Heinisch G., Kirchner I., Kurzmann I., Lötsch G., Waglechner R. (1983) Arch. Pharm. (Weinheim)316: 508Google Scholar
  15. [15]
    Garland I., Hatton L., Leeds W., Parnell E. (1976) German Offen. 2557956; (1976) Chem. Abstr.85: 177470Google Scholar
  16. [16]
    Heinisch G., Huber T. (1989) J. Heterocycl. Chem.26: 1787Google Scholar
  17. [17]
    Varlet J. M., Collignon N., Savignac P. (1978) Synth. Commun.8: 335Google Scholar
  18. [18]
    Neuhaus D., Williamson M. P. (1989) The Nuclear Overhauser Effect in Structural and Conformational Analysis. VCH Publishers, New York, p. 380Google Scholar
  19. [19]
    Heinisch G., Holzer W. (1990) Tetrahedron Lett.31: 3109Google Scholar
  20. [20]
    Heinisch G., Holzer W. (1990) Monatsh. Chem.121: 837Google Scholar
  21. [21]
    Easmon J., Heinisch G., Holzer W. (1989) Heterocycles29: 1399Google Scholar
  22. [22]
    In the 80HMz1H-nmr spectrum of4, the pyridazine H-4 signal could not be identified unambiguously due to an overlap with phenyl-H resonances. In the NOE difference spectrum, however, the four lines of pyridazine H-4 emerged clearly. Their position was confirmed independently by pseudo-INDOR experiments irradiating multiplet lines of pyridazine H-6Google Scholar
  23. [23]
    Kinns M., Sanders J. M. K. (1984) J. Magn. Reson.56: 518Google Scholar
  24. [24]
    An unambiguous differentiation between these protons and the corresponding protons of the other phenyl group is not possibleGoogle Scholar
  25. [25]
    The only modest yield results from incomplete consumption of the ketone3 Google Scholar

Copyright information

© Springer-Verlag 1991

Authors and Affiliations

  • Gottfried Heinisch
    • 1
  • Wolfgang Holzer
    • 1
  • Thierry Huber
    • 1
  1. 1.Institute of Pharmaceutical ChemistryUniversity of ViennaWienAustria

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