Advertisement

Chemistry of Heterocyclic Compounds

, Volume 15, Issue 3, pp 265–268 | Cite as

Synthesis of pyridine and pyrimidine derivatives by reaction of pyrylium salts with ureas, thioureas, and isothioureas

  • é. A. Zvezdina
  • M. P. Zhdanova
  • G. N. Dorofeenko
Article

Abstract

2,4,6-Triphenylpyrylium perchlorate is converted to 2,4,6-triphenylpyridine in reactions with urea and N-acetyl- and N,N-dimethylureas, whereas it is converted to 1,2,4,6-tetraphenylpyridinium perchlorate on reaction with N,N′-diphenylurea. The reaction of pyrylium perchlorates with thiosemicarbazide and semicarbazide leads to 1-thiocarbamido- and 1-carbamidopyridinium salts. The latter reacts with 2,4,6-triphenylpyrylium perchlorate to give 1-aminopyridinium salts, which were acylated with acetic anhydride. Difficult-to-obtain 2-alkylthio-4,6-diarylpyrimidines were synthesized in 40–93% yields by the reaction of 2,4,6-triarylpyrylium salts with S-alkylisothioureas.

Keywords

Acetic Urea Organic Chemistry Pyridine Anhydride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    M. P. Zhdanova, é. A. Zvezdina, and G. N. Dorofeenko, Khim. Geterotsikl. Soedin., No. 4, 456 (1978).Google Scholar
  2. 2.
    A. N. Kost (editor), General Laboratory Manual of Organic Chemistry [in Russian], Mir, Moscow (1965), p. 376.Google Scholar
  3. 3.
    A. T. Balaban and C. Nenitzescu, Liebigs Ann., 625, 66 (1959).Google Scholar
  4. 4.
    R. M. Dodson and J. K. Seyler, J. Org. Chem., 16, 461 (1951).Google Scholar
  5. 5.
    A. T. Balaban, Tetrahedron, 24, 5059 (1968).Google Scholar
  6. 6.
    G. N. Dorofeenko and S. V. Krivun, Zh. Obshch. Khim., 34, 105 (1964).Google Scholar
  7. 7.
    G. N. Dorofeenko, é. A. Zvezdina, M. P. Zhdanova, V. V. Derbenev, and E. S. Matskovskaya, Khim. Geterotsikl. Soedin., No. 8, 1036 (1974).Google Scholar
  8. 8.
    J. Bapat, R. Blade, A. Boulton, J. Epsztain, A. Katritzky, J. Lewis, P. Molina-Buendia, Nie Pai-Lin, and C. Ramsden, Tetrahedron Lett., No. 31, 2691 (1976).Google Scholar
  9. 9.
    G. N. Dorofeenko, A. N. Narkevich, Yu. A. Zhdanov, O. E. Shelepin, and T. G. Soroka, Khim. Geterotsikl. Soedin., No. 2, 223 (1970).Google Scholar
  10. 10.
    Beilstein, 20–22, 87, 180 (1935).Google Scholar

Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • é. A. Zvezdina
    • 1
  • M. P. Zhdanova
    • 1
  • G. N. Dorofeenko
    • 1
  1. 1.Scientific-Research Institute of Physical and Organic ChemistryRostov State UniversityRostov-on-Don

Personalised recommendations