Synthesis, structure, and properties of 1,3,5-triarylpyridazines


Treatment of γ-bromodypnone with arylhydrazines gives differently structured products, i.e. γ-bromo-dypnone hydrazones, 1-aryl-3,5-diphenyl-1,4-dihydropyridazines, 1-aryl-3,5-diphenyl-1,6-dihydro-pyridazines, and aromatic 1,3,5-triarylpyridazinium salts. We have studied the pattern of formation of all of the products and their properties. Heating an alcohol solution of 1,3,5-triphenyl-1,4-dihydro-pyridazine gives N,2,4-triphenyl-1H-pyrrole-1-amine or to a 1,3,5-triphenylpyridazinium salt dependent upon the acidity of the medium. The product of addition of HBr to the 1,6-dihydropyridazine system is 5-bromo-1-(4-nitrophenyl)-3,5-diphenyl-1,4,5,6-tetrahydropyridazine.


γ-bromodypnone 1,3,5-triarylpyridazinium bromide 1,3,5-triaryl-1,4-dihydropyridazine 1,3,5-triaryl-1,6-dihydropyridazine N,2,4-triphenyl-1H-pyrrole-1-amine 


  1. 1.
    D. W. Combs, K. Reese, L. A. M. Cornelius, J. W. Gunnet, E. V. Cryan, K. S. Granger, J. J. Jordan, and K. T. Demarest, J. Med. Chem., 38, 4880 (1995).CrossRefGoogle Scholar
  2. 2.
    G. Cignarella, D. Barlocco, and S. Villa, J. Heterocycl. Chem., 35, 1161 (1998).CrossRefGoogle Scholar
  3. 3.
    M. Tišler and P. Kolar, Adv. Heterocycl. Chem., 75, 167 (2000).Google Scholar
  4. 4.
    J. P. Hieble and R. R. Ruffolo, Progr. Drug Res., 47, 81 (1996).Google Scholar
  5. 5.
    D. Wensbo and S. Gronowitz, Tetrahedron, 52, 14975 (1996).CrossRefGoogle Scholar
  6. 6.
    L. M. Potikha and V. A. Kovtunenko, Khim. Geterotsikl. Soedin., 626 (2007). [Chem. Heterocycl. Comp., 43, 523 (2007)].Google Scholar
  7. 7.
    L. M. Potikha, V. A. Kovtunenko, A. V. Turov, G. V. Palamarchuk, R. I. Zubatyuk, and O. V. Shishkin, Khim. Geterotsikl. Soedin., 404 (2009). [Chem. Heterocycl. Comp., 45, 327 (2009)].Google Scholar
  8. 8.
    D. M. Lemal and T. W. Rave, Tetrahedron, 19, 1119 (1963).CrossRefGoogle Scholar
  9. 9.
    M. T. Cocco, C. Congiu, A. Maccioni, and A. Plumitallo, Gazz. Chim. Ital., 118, 187 (1988).Google Scholar
  10. 10.
    A. S. Morkovnik and O. Yu. Okhlobystin, Khim. Geterotsikl. Soedin., 551 (1985). [Chem. Heterocycl. Comp., 21, 461 (1985)].Google Scholar
  11. 11.
    M. E. Scott, Y. Bethuel, and M. Lautens, J. Am. Chem. Soc., 129, 1482 (2007).CrossRefGoogle Scholar
  12. 12.
    M. Hartnagel, K. Grimm, and H. Mayr, Liebigs Ann. Chem., 71 (1997).Google Scholar
  13. 13.
    B. A. Carson, W. A. Sheppard, and O. W. Webster, J. Am. Chem. Soc., 97, 5291 (1975).CrossRefGoogle Scholar
  14. 14.
    H. H. Wasserman, N. E. Aubrey, and H. E. Zimmerman, J. Am. Chem. Soc., 75, 96 (1953).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • L. M. Potikha
    • 1
  • V. A. Kovtunenko
    • 1
  • A. V. Turov
    • 1
  1. 1.Taras Shevchenko National UniversityKievUkraine

Personalised recommendations