Chemistry of Heterocyclic Compounds

, Volume 17, Issue 9, pp 932–936 | Cite as

Electrophilic substitution in n-aryl-2-pyrazolines: Reactions with 1,3-dithioles

  • I. M. Gella
  • V. N. Vakula
  • V. D. Orlov
Article
  • 23 Downloads

Abstract

Dyes that absorb at 525–580 nm were obtained by the reaction of derivatives of 1,3-dithiolium iodide (or perchlorate) with 1-phenyl-3,5-di-R-2-pyrazolines, N,N-dimethylaniline, and benzaldehyde N-methylphenylhydrazone. It was demonstrated by alternative synthesis that the reaction takes place in the para position of the N-phenyl group. Dyes can be obtained in two steps from 2-dimethylamino-1,3-dithioles and activated aromatic compounds with subsequent oxidation of the intermediate leuco compounds with air oxygen.

Keywords

Oxidation Oxygen Organic Chemistry Iodide Perchlorate 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    E. Campaigne and R. D. Hamilton, Quart. Rep. Sulfur Chem., 5, 275 (1970).Google Scholar
  2. 2.
    M. Narita and C. U. Pittman, Jr., Synthesis, No. 8, 489 (1976).Google Scholar
  3. 3.
    J. Nakayama, K. Fujiwara, and M. Hoshino, Bull. Chem. Soc. Jpn., 49, 3567 (1976).Google Scholar
  4. 4.
    J. Nakayama, Synthesis, No. 3, 171 (1975).Google Scholar
  5. 5.
    V. D. Orlov and A. I. Roberman, Dokl. Akad. Nauk SSSR, 246, 888 (1979).Google Scholar
  6. 6.
    V. D. Orlov, A. I. Roberman, A. I. Rybachenko, and V. F. Lavrushin, Khim. Geterotsikl. Soedin., No. 11, 1538 (1977).Google Scholar
  7. 7.
    A. F. Plue, U.S. Patent No. 2976295; Chem. Abstr., 55, 16569 (1961).Google Scholar
  8. 8.
    L. A. Kutulya, A. E. Shevchenko, and Yu. N. Surov, Khim. Geterotsikl. Soedin., No. 2, 250 (1975).Google Scholar
  9. 9.
    G. F. Duffin and J. D. Kendall, J. Chem. Soc., No. 1, 408 (1954).Google Scholar
  10. 10.
    L. Szucs and A. Bradlerova, Z. Chem., 15, 477 (1975).Google Scholar
  11. 11.
    J. Nakayama, Synthesis, No. 1, 38 (1975).Google Scholar
  12. 12.
    J. Degani and R. Fochi, J. Chem. Soc., Perkin Trans. I, No. 17, 1886 (1976).Google Scholar
  13. 13.
    A. V. Luzanov, A. A. Sukhorukov, and V. É. Umanskii, Teor. Éksp. Khim., 10, 456 (1974).Google Scholar
  14. 14.
    L. A. Kutulya, V. F. Morina, A. E. Shevchenko, and Yu. N. Surov, Zh. Prikl. Khim., 27, 76 (1977).Google Scholar
  15. 15.
    E. Campaigne and R. D. Hamilton, J. Org. Chem., 29, 1711 (1964).Google Scholar
  16. 16.
    K. Hirai, Tetrahedron, 27, 4003 (1971).Google Scholar
  17. 17.
    R. Zahradnik and R. Polak, Fundamentals of Quantum Chemistry [Russian translation], Mir, Moscow (1977), p. 230.Google Scholar
  18. 18.
    E. Faughanel, J. Prakt. Chem., 317, 123 (1975).Google Scholar
  19. 19.
    E. Campaigne and N. W. Jacobsen, J. Org. Chem., 29, 1703 (1964).Google Scholar
  20. 20.
    K. M. Pazdro and W. Polaczkowa, Rocz. Chem., 45, 811 (1971).Google Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • I. M. Gella
    • 1
  • V. N. Vakula
    • 1
  • V. D. Orlov
    • 1
  1. 1.Kharkov Scientific-Research Institute of Endocrinology and the Chemistry of HormonesA. M. Gor'kii Kharkov State UniversityKharkov

Personalised recommendations