Chemistry of Heterocyclic Compounds

, Volume 9, Issue 7, pp 891–894 | Cite as

N-Anions of heteroaromatic amines

VI. Alkylation of N-anions of heteroaromatic amines in liquid ammonia with alkyl halides and benzyl chloride
  • V. I. Sokolov
  • A. F. Pozharskii
  • B. I. Ardashev


The alkylation of the N-anions of 2- and 4-aminopyridines, 1-aminoisoquinoline, and 2-amino-1-ethylbenzimidazole with C2-C4 alkyl halides in liquid ammonia leads to the formation of a mixture of the products of mono- and dialkylation at the NH2 group (usually with a predominance of the latter). The role of stepwise processes and the yield of the dialkyl derivative increase on passing from alkyl bromides to iodides and from the heavier and branched radicals (C4H9, i-C3H7) to lighter radicals (C2H5).


Ammonia Bromide Organic Chemistry Iodide Alkylation 
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Literature cited

  1. 1.
    A. F. Pozharskii and A. A. Konstantinchenko, Khim. Geterotsikl. Soedin., 363 (1973).Google Scholar
  2. 2.
    Yu. P. Andreichikov, É. A. Zvezdina, I. S. Kashparov, V. M. Mar'yanovskii, A. F. Pozharskii, and A. M. Simonov, USSR Authors' Certificate No. 330,167 (1969); Byul. Izobret., No. 5, 81 (1972).Google Scholar
  3. 3.
    A. F. Pozharskii, É. A. Zvezdina, I. S. Kashparov, Yu. P. Andreichikov, V. M. Mar'yanovskii, and A. M. Simonov, Khim. Geterotsikl. Soedin., 1230 (1971).Google Scholar
  4. 4.
    Organic Syntheses [Russian translation], Vol. 3, IL, Moscow (1952), p. 31.Google Scholar
  5. 5.
    J. Renault and J. Berlot, Compt. Rend., C, 270, 358 (1970).Google Scholar
  6. 6.
    D. Jerchel and L. Jakob, Chem. Ber., 91, 1266 (1958).Google Scholar
  7. 7.
    T. Kauffmann and R. Nürnberg, Chem. Ber., 100, 3427 (1967).Google Scholar
  8. 8.
    É. A. Zvezdina, A. F. Pozharskii, and V. I. Sokolov, Khim. Geterotsikl. Soedin., 419 (1970).Google Scholar
  9. 9.
    J. Bernstein, B. Stearns, M. Dexster, and N. Brunswick, J. Amer. Chem. Soc., 69, 1147 (1947).Google Scholar
  10. 10.
    C. Hauser and M. Weiss, J. Org. Chem., 14, 310 (1949).Google Scholar
  11. 11.
    C. Hunger, I. Kebrle, A. Rossi, and K. Hoffman, Helv. Chim. Acta, 44, 1273 (1961).Google Scholar
  12. 12.
    F. F. Blické and M. U. Tsao. J. Amer. Chem. Soc., 68, 905 (1946).Google Scholar
  13. 13.
    A. Katritzky and A. Waring, J. Chem. Soc., 1544 (1962).Google Scholar
  14. 14.
    B. A. Arbuzov, V. M. Zoroastrova, and M. P. Osipova, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 2163 (1961).Google Scholar

Copyright information

© Plenum Publishing Corporation 1975

Authors and Affiliations

  • V. I. Sokolov
    • 1
  • A. F. Pozharskii
    • 1
  • B. I. Ardashev
    • 1
  1. 1.Novocherkassk Polytechnic InstituteNovocherkassk. Rostov State UniversityRostov-on-Don

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