Chemistry of Heterocyclic Compounds

, Volume 10, Issue 5, pp 563–566 | Cite as

Azaindole derivatives

XLIV. Peculiarities of the synthesis of 7-azaindolines during the reactions of 2,6-dichloro-3-(β-chloroethyl-4-methylpyridine (trichlorocollidine) with primary aromatic and sterically hindered amines
  • D. M. Krasnokutskaya
  • L. N. Yakhontov
Article
  • 24 Downloads

Abstract

As in the case of N-substituted anilines, trichlorocollidine forms 6-chloro-7-azaindoline derivatives rather than 6-amino-7-azaindoline derivatives with sterically hindered primary amines of the β-phenylisopropylamine type. On passing to tert-butylamine, nucleophilic attack at the α and α′ positions of the pyridine ring proves to be sterically impossible, and dehydrohalogenation of trichlorocollidine to 2,6-dichloro-3-vinyl-4-methylpyridine becomes the principal reaction.

Keywords

Organic Chemistry Pyridine Aniline Primary Amine Pyridine Ring 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    M. Ya. Uritskaya, V. A. Loginova, and L. N. Yakhontov, Khim. Geterotsikl. Soedin., 1370 (1973).Google Scholar
  2. 2.
    L. N. Yakhontov and M. V. Rubtsov, Zh. Obshch. Khim., 30, 3300 (1960).Google Scholar
  3. 3.
    L. N. Yakhontov and M. V. Rubtsov, Zh. Obshch. Khim., 34, 493 (1964).Google Scholar
  4. 4.
    L. N. Yakhontov, M. S. Sokolova. and M. V. Rubtsov. Khim. Geterotsikl. Soedin., No. 1, 455 (1967).Google Scholar
  5. 5.
    L. N. Yakhontov, D. M. Krasnokutskaya, A. N. Akalaev, I. N. Palant, and Yu. I. Vainshtein, Khim. Geterotsikl. Soedin., 789 (1971).Google Scholar
  6. 6.
    A. Albert and E. Serjeant, Determination of Ionization Constants; A Practical Manual, Chapman and Hall (1972).Google Scholar
  7. 7.
    L. N. Yakhontov, M. S. Sokolova, and M. V. Rubtsov, Khim. Geterotsikl. Soedin., 74 (1966).Google Scholar
  8. 8.
    L. N. Yakhontov, D. M. Krasnokutskaya, and M. V. Rubtsov, Khim. Geterotsikl. Soedin., 66 (1966).Google Scholar

Copyright information

© Plenum Publishing Corporation 1975

Authors and Affiliations

  • D. M. Krasnokutskaya
    • 1
  • L. N. Yakhontov
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical Chemistry InstituteMoscow

Personalised recommendations