Advertisement

Chemistry of Heterocyclic Compounds

, Volume 16, Issue 11, pp 1153–1156 | Cite as

Synthesis of 3-azafluorene and 2h-2-methylindeno[1,2-c]pyridine

  • N. S. Prostakov
  • P. K. Radzhan
  • A. T. Soldatenkov
Article
  • 47 Downloads

Abstract

4-Methyl-3-phenylpyridine was isolated from the mixture of four isomeric methylphenyl-pyridines formed in the condensation of crotonaldehyde with phenylacetaldehyde (β-phenylethanol or phenylacetylene) with ammonia in the presence of a cadmium-calcium phosphate catalyst. 4-Methyl-3-phenylpyridine was converted to 3-azafluorene by catalytic dehydrocyclization. A representative of a new series of pseudoazulenes, viz., 2H-2-methylindeno[1,2-c]-pyridine, was obtained by treatment of 3-azafluorene methiodide with sodium hydroxide solution; the product was a crystalline black substance that remained unchanged during storage in air for 1 month.

Keywords

Phosphate Ammonia Hydroxide Pyridine Sodium Hydroxide 
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.
    N. S. Prostakov, A. T. Soldatenkov, V. O. Fedorov, S. Mobio, and M. A. Galiullin, Khim. Geterotsikl. Soedin., No. 11, 1511 (1980).Google Scholar
  2. 2.
    G. V. Boyd, J. Chem. Soc., No. 1, 55 (1955).Google Scholar
  3. 3.
    W. Treibs and J. Beger, Lieb. Ann., 652, 192 (1962).Google Scholar
  4. 4.
    A. E. Chichibabin and D. I. Orochko, Zh. Russk. Khim. Obshchestva, 62, 1201 (1930).Google Scholar
  5. 5.
    N. S. Prostakov, A. T. Soldatenkov, and V. O. Fedorov, Zh. Org. Khim., 15, 1109 (1979).Google Scholar
  6. 6.
    N. S. Prostakov, K. D. Matthew, and V. A. Kurichev, Khim. Geterotsikl. Soedin., No. 5, 876 (1967).Google Scholar
  7. 7.
    C. Mayor and C. Wentrup, J. Am. Chem. Soc., 97, 7467 (1975).Google Scholar
  8. 8.
    J. N. Chatterjea and K. Prasad, Chem. Ber., 93, 1740 (1960).Google Scholar
  9. 9.
    C. Osuch and R. Levine, J. Am. Chem. Soc., 78, 1725 (1956).Google Scholar
  10. 10.
    J. M. Bonnier, J. Court, and T. Fay, Bull. Soc. Chim. Fr., No. 4, 1204 (1967).Google Scholar

Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • N. S. Prostakov
    • 1
  • P. K. Radzhan
    • 1
  • A. T. Soldatenkov
    • 1
  1. 1.Patrice Lumumba People's Friendship UniversityMoscow

Personalised recommendations