Chemistry of Heterocyclic Compounds

, Volume 13, Issue 3, pp 307–311 | Cite as

Introduction of substituents in the pyridine proton of 7-azaindoline

  • D. M. Krasnokut-skaya
  • L. N. Yakhontov
Article
  • 26 Downloads

Abstract

Electropilic substitution (nitration, bromination, and chlorination) of 4-methyl-6-chloro-7-azaindoline (and its N-acetyl derivative) takes place in the 5 position. 4-Methyl-5-amino-7-azaindoline, 4-methyl-5-nitro-7-azaindoline, and 1-acetyl-4-methyl-5-amino-6-chloro-7-azaindoline were obtained by reduction of 1-acetyl-4-methyl-5-nitro-6-chloro-7-azaindoline under various conditions. A method was developed for the preparation of a new three-ring system — 1,2,3-oxadiazolo[5,4-b]-pyrrolo[2,3-e]pyridine.

Keywords

Organic Chemistry Pyridine Nitration Pyridine Proton 

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Literature cited

  1. 1.
    I. N. Palant, D. M. Krasnokut-skaya, K. F. Turchin, S. S. Anisimova, and Yu. I. Vainshtein, Khim. Geterotsikl. Soedin., No. 9, 1277 (1975).Google Scholar
  2. 2.
    M. M. Robison and B. L. Robison, J. Am. Chem. Soc. 78, 1247 (1956).Google Scholar
  3. 3.
    L. N. Yakhontov, V. A. Azimov, and E. I. Lapan, Tetrahedron Lett., 1909 (1969).Google Scholar
  4. 4.
    M. M. Robison, B. L. Robison, and F. P. Butler, J. Am. Chem. Soc., 81, 743 (1959).Google Scholar
  5. 5.
    L. N. Yakhontov, M. Ya. Uritskaya, and M. V. Rubtsov, Zh. Obshch. Khim., 34, 1449 (1964).Google Scholar
  6. 6.
    L. N. Yakhontov, Usp. Khim., 37, 1258 (1968).Google Scholar
  7. 7.
    D. M. Krasnokut-skaya and L. N. Yakhontov, Inventors' Certificate No. 453403 (1973); Byul. Izobr., No. 46, 55 (1974).Google Scholar

Copyright information

© Plenum Publishing Corporation 1977

Authors and Affiliations

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

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