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Monatshefte für Chemie / Chemical Monthly

, Volume 123, Issue 12, pp 1163–1173 | Cite as

On the structure of guanylhydrazones derived from aromatic aldehydes

  • Wolfgang Holzer
  • Zoltán Györgydeák
Organische Chemie Und Biochemie

Summary

The synthesis of some novel guanylhydrazones derived from aromatic aldehydes (benzylideneaminoguanidines) is described. Structural assignments of these compounds as well as of some already known congeners, particularly with respect to the configuration of the HC=N double bond, were achieved using1H- and13C-NMR data as well as homonuclear NOE difference spectroscopy.

Keywords

Benzaldehyde guanylhydrazones, substituted Benzylideneaminoguanidines 1H-NMR spectroscopy 13C-NMR spectroscopy NOE Difference spectroscopy 

Zur Struktur von Guanylhydrazonen aromatischer Aldehyde

Zusammenfassung

Die Synthese einiger neuer Guanylhydrazone abgeleitet von aromatischen Aldehyden (Benzylidenaminoguanidine) wird beschrieben. Die Strukturzuordnung bei diesen Verbindungen sowie bei einigen literaturbeschriebenen Analoga — besonders im Hinblick auf die Konfiguration an der HC=N Doppelbindung — erfolgte mittels1H- und13C-NMR Spektroskopie sowie mit Hilfe homonuklearer NOE-Differenzspektroskopie.

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References

  1. [1] (a)
    For instance: Piesche L., Hilse H., Oehme P. (1979) Pharmazie34: 332;Google Scholar
  2. [1] (b)
    Hagen A., Frömmel B., Kühmstedt H., Wunderlich I., Kottke K., Göres E. (1979) Pharmazie34: 330;Google Scholar
  3. [1] (c)
    Mamolo M. G., Vio L., Fabris B., Fischetti F., Carretta R., Giraldi T. (1986) Il Farmaco-Ed. Sci.41: 873;Google Scholar
  4. [1] (d)
    Vio L., Mamolo M. G., Pellizer G. (1988) Arch. Pharm. (Weinheim)321: 713;Google Scholar
  5. [1] (e)
    Foye W. O., Almassian B., Eisenberg M. S., Maher T. J. (1990) J. Pharm. Sci.79: 527Google Scholar
  6. [2]
    Vio L., Mamolo M. G. (1983) Il Farmaco-Ed. Sci.38: 255Google Scholar
  7. [3]
    American Home Products Corp. (Bruce W. F., Baum T., inv.) (1969) Ger. Offen. 1, 802, 394; 08 May 1969; (1969) C. A.71: 60991zGoogle Scholar
  8. [4]
    Sandoz-Wander, Inc. (Houlihan W. J., Manning R. E., inv.) (1972) U. S. 3, 657, 337; 18 Apr 1972; (1972) C. A.77: 48073tGoogle Scholar
  9. [5]
    Tsujikawa T., Hayashi M., Masuda K. (1975) Yakugaku Zasshi95: 1271; (1976) C. A.84: 121759xGoogle Scholar
  10. [6] (a)
    Schütz S., Meyer K., Krätzer H. (1969) Arznm.-Forsch. /Drug Res.19: 69;Google Scholar
  11. [6] (b)
    Wollert U. (1969) Arznm.-Forsch. /Drug Res.19: 680;Google Scholar
  12. [6] (c)
    Mutschler E., Röttger E. (1976) Arch. Pharm. (Weinheim)309: 372Google Scholar
  13. [7]
    Nishimura T., Yamazaki C., Toku H., Yoshii S., Hasegawa K., Saito M., Nagaki D. (1974) Chem. Pharm. Bull.22: 2444Google Scholar
  14. [8]
    Mamolo M. G., Vio L., Banfi E., Cinco M. (1986) Eur. J. Med. Chem.-Chim. Ther.21: 467Google Scholar
  15. [9] (a)
    DoAmaral J. R., French F. A., Blanz E. J. Jr., French D. A. (1971) J. Med. Chem.14: 862;Google Scholar
  16. [9] (b)
    Werbel L. M., Hung J., McNamara D., Ortwine D. F. (1985) Eur. J. Med. Chem.-Chim. Ther.20: 363Google Scholar
  17. [10]
    Sundberg R. J., Dahlhausen D. J., Manikumar G., Mavunkel B., Biswas A., Srinivasan V., Musallam H. A., Reid W. A. Jr., Ager A. L. (1990) J. Med. Chem.33: 298Google Scholar
  18. [11]
    Korytnyk W., Angelino N., Dave C., Caballes L. (1978) J. Med. Chem.21: 507Google Scholar
  19. [12]
    Choay S. A. (Orzalesi H., Castel J., inv.) (1978) Ger. Offen. 2, 745, 596; 20 Apr 1978; (1978) C. A.89: 163248pGoogle Scholar
  20. [13]
    (a) American Home Products Corp. (Bruce W. F., inv.) (1973) U. S. 3, 775, 405; 27 Nov 1973; (1974) C. A.80: 59693h; (b) American Home Products Corp. (Bruce W. F., inv.) (1974) U. S. 3, 850, 915;26 Nov 1974; (1975) C. A.82: 155791aGoogle Scholar
  21. [14]
    Shell Oil Co. (Kodama J. K., Haynes G. R., Albert J. R., inv.) (1976) U. S. 3, 975, 533; 17 Aug 1976; (1976) C. A.85: 130539yGoogle Scholar
  22. [15]
    Pitzele B. S., Moormann A. E., Gullikson G. W., Albin D., Bianchi R. G., Palicharla P., Sanguinetti E. L., Walters D. E. (1988) J. Med. Chem. 31: 138Google Scholar
  23. [16]
    Baum T., Eckfeld D. K., Metz N., Dinish J. L., Rowles G., van Pelt R., Shropshire A. T., Fernandez S. P., Gluckman M. I., Bruce W. F. (1969) Experientia25: 1066Google Scholar
  24. [17] (a)
    King H., Wright J. (1948) J. Chem. Soc.: 2314;Google Scholar
  25. [17] (b)
    Tomchin A. B., Ioffe I. S., Lepp Yu V., Timofeeva T. N. (1974) Zh. Org. Khim.10: 371; (1974) C. A.81: 3896eGoogle Scholar
  26. [18]
    Tsujikawa T., Mizuta E., Hayashi M. (1976) Yakugaku Zasshi96: 125; (1976) C. A.85: 108218wGoogle Scholar
  27. [19]
    Shearer C. M., DeAngelis N. J. (1979) J. Pharm. Sci.68: 1010Google Scholar
  28. [20] (a)
    Ercoli A., Gardi R., Gladiali S., Tenconi F., Vitali R. (1977) Boll. Chim. Farm.116: 218;Google Scholar
  29. [20] (b)
    Axelson M., Sjovall J., Drakenberg T., Forsen S. (1978) Anal. Lett.B 11: 229Google Scholar
  30. [21]
    Heinisch G., Holzer W. (1990) Tetrahedron Lett.31: 3109Google Scholar
  31. [22]
    Heinisch G., Holzer W. (1990) Monatsh. Chem.121: 837Google Scholar
  32. [23]
    Easmon J., Heinisch G., Holzer W. (1989) Heterocycles29: 1399Google Scholar
  33. [24]
    It should be mentioned that due to chemical exchange (slow compared to the NMR-timescale) it is not possible to irradiate different types of NH2 or NH protons selectively. Thus, in all NOE difference experiments saturation transfer between NH2 and NH (OH) protons was observed (see also footnote in Table 1)Google Scholar
  34. [25] (a)
    Kalinowski H.-O., Berger S., Braun S. (1984)13C-NMR Spektroskopie. Thieme, New York, p. 457;Google Scholar
  35. [25] (b)
    Gil V. M. S., von Philipsborn W. (1989) Magn. Reson. Chem.27: 409Google Scholar
  36. [26] (a)
    For instance: Karabatsos G. J., Taller R. A., Vaine F. M. (1963) J. Am. Chem. Soc.85: 2326;Google Scholar
  37. [26] (b)
    Bell C. F., Mortimore G. R. (1975) Org. Magn. Reson.7: 512Google Scholar
  38. [27]
    LeCocq C., Lallemand J.-Y. (1981) J. Chem. Soc. Chem. Commun.: 150Google Scholar
  39. [28]
    Ref. 25, p. 220Google Scholar
  40. [29]
    Bunnell C. A., Fuchs P. L. (1977) J. Org. Chem.42: 2614Google Scholar
  41. [30] (a)
    Kalchhauser H., Robien W. (1985) J. Chem. Inform. Comput. Sci.25: 103;Google Scholar
  42. [30] (b)
    SADTLER Collection, SADTLER Research Laboratories, Philadelphia, PA, USAGoogle Scholar
  43. [31] (a)
    Gothe L., Salome S., Werner P.-E. (1979) Cryst. Struct. Commun.8: 1;Google Scholar
  44. [31] (b)
    Carpy A., Saux M., Montagut M. (1984) Acta Cryst.C 40: 1265Google Scholar
  45. [32]
    Hegarty A. F., O'Mahony T. A. F., Quain P., Scott F. L. (1973) J. Chem. Soc. Perkin Trans.II: 2047Google Scholar
  46. [33]
    Kinns M., Sanders J. K. M. (1984) J. Magn. Reson.56: 518Google Scholar
  47. [34]
    Thiele J. (1892) Ann. Chem.270: 1Google Scholar
  48. [35]
    Grammaticakis P. (1952) Bull. Soc. Chim. Fr.: 446Google Scholar
  49. [36]
    Thiele J., Bihan R. (1898) Ann. Chem.302: 299Google Scholar
  50. [37]
    Beyer H., Hetzheim A., Honeck H., Ling D., Pyl T. (1968) Chem. Ber.101: 3151Google Scholar
  51. [38]
    Finnegan W. G., Henry R. A., Smith G. B. L. (1952) J. Am. Chem. Soc.74: 2981Google Scholar
  52. [39]
    Atkinson M. R., Komzak A. A., Parkes E. A., Polya J. B. (1954) J. Chem. Soc.: 4508Google Scholar
  53. [40]
    Micovic V. M., Mihailovic M. L. (1952) Rec. trav. chim.71: 970Google Scholar
  54. [41]
    For the free base9 see: Bokaldere R., Grinsteins V., Medne K. (1969) Latv. PSR Zinat. Akad. Vestis, Kim. Ser.: 347; (1969) C. A.71: 101495mGoogle Scholar
  55. [42]
    For the hydroiodide salt12 · HI see: Zelenin K. N., Sergutina V. P., Solod O. V., Pinson V. V. (1987) Khim. Geterotsikl. Soedin.: 1071; (1988) C. A.108: 166788mGoogle Scholar
  56. [43]
    Scott F. L., Morrish W. N., Reilly J. (1957) J. Org. Chem.22: 692Google Scholar

Copyright information

© Springer-Verlag 1992

Authors and Affiliations

  • Wolfgang Holzer
    • 1
  • Zoltán Györgydeák
    • 2
  1. 1.Institut für Pharmazeutische ChemieUniversität WienWienAustria
  2. 2.Department of Organic ChemistryUniversity of DebrecenDebrecenHungary

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