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Chemistry of Heterocyclic Compounds

, Volume 42, Issue 1, pp 70–76 | Cite as

3-Acetyl-4-methylpyrido[2,1-a]-isoquinolin-2-ones. [2+4] cyclocondensation of 3,4-dihydroisoquinolines with triacetylmethane

  • O. V. Gulyakevich
  • P. V. Kurman
  • A. S. Lyakhov
  • A. L. Mikhal’chuk
Article

Abstract

Treatment of 3,4-dihydroisoquinolines with triacetylmethane in refluxing alcohol for 2-3 h gave 3-acetyl-4-methylpyrido[2,1-a]isoquinolin-2-ones. Their basic physicochemical properties have been studied.

Keywords

azomethines benzo[a]quinolizines 3,4-dihydroisoquinolines Schiff’s base pyrido[2,1-a]-isoquinolines triacetylmethane annelation [2+4] cyclocondensation 

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References

  1. 1.
    A. A. Akhrem, O. V. Gulyakevich, and A. L. Mikhal’chuk, in: Enamines in Organic Synthesis [in Russian], Ural Section, Russian Academy of Sciences, Yekaterinburg (2001), p. 47.Google Scholar
  2. 2.
    A. A. Akhrem, O. V. Gulyakevich, and A. L. Mikhal’chuk, in: V. G. Kartsev and G. A. Tolstikov (editors), Nitrogen Heterocycles and Alkaloids [in Russian], Vol. 1, Iridium Press, Moscow (2001), p. 31.Google Scholar
  3. 3.
    D. B. Rubinov, M. V. Budnikova, T. A. Zheldakova, and A. L. Mikhal’chuk, in: V. G. Kartsev and G. A. Tolstikov (editors), Nitrogen Heterocycles and Alkaloids [in Russian], Vol. 1, Iridium Press, Moscow (2001), p. 503.Google Scholar
  4. 4.
    A. L. Mikhal’chuk, O. V. Gulyakevich, V. P. Peresada, A. M. Likhosherstov, and A. A. Akhrem, Dokl. Russ. Acad. Sci, 356, 769 (1997).Google Scholar
  5. 5.
    O. V. Gulyakevich, A. L. Mikhal’chuk, and A. A. Akhrem, Izv. Akad. Nauk, Ser. Khim., 1358 (1997).Google Scholar
  6. 6.
    A. L. Mikhal’chuk, O. V. Gulyakevich, and A. A. Akhrem, Zh. Prikl. Khim., 71, 645 (1998).Google Scholar
  7. 7.
    J. R. Huff, P. S. Anderson, J. J. Baldwin, B. V. Clineschmitt, J. P. Guare, V. J. Lotti, D. J. Pettibone, W. C. Randale, and J. P. Vacca, J. Med. Chem., 28, 1756 (1985).Google Scholar
  8. 8.
    E. S. Viri, I. Toth, G. T. Somogyi, L. Szabo, L. G. Harsing, Jr., and Cs. Szantay, J. Med. Chem., 30, 1355 (1987).Google Scholar
  9. 9.
    T. Kametani, S. A. Surgenor, and K. Fukumoto, Heterocycles, 14, 303 (1980).Google Scholar
  10. 10.
    O. V. Gulyakevich, A. L. Mikhal’chuk, A. I. Verenich, D. B. Rubinov, A. A. Zenyuk, and A. A. Akhrem, in: Enamines in Organic Synthesis [in Russian], Ural Section, Russian Academy of Sciences, Yekaterinburg (1996), p. 111.Google Scholar
  11. 11.
    A. L. Mikhal’chuk, O. V. Gulyakevich, and A. A. Akhrem, Khim. Geterotsikl. Soedin., 1239 (1993).Google Scholar
  12. 12.
    A. L. Mikhal’chuk, O. V. Gulyakevich, A. A. Zenyuk, Yu. V. Shklyaev, V. S. Shklyaev, and A. A. Akhrem, Zh. Obshch. Khim., 63, 1891 (1993).Google Scholar
  13. 13.
    A. A. Akhrem, B. B. Kuz’mitskii, F. A. Lakhvich, V. A. Khripach, and Yu. L. Zhuravkov, in: The Chemistry and Biology of Immunoregulators [in Russian], Zinatne, Riga (1985), p. 265.Google Scholar
  14. 14.
    A. A. Akhrem, F. A. Lakhvich, V. N. Pshenichnyi, O. V. Gulyakevich, I. I. Petrusevich, B. B. Kuz’mitskii, N. K. Kevra, G. I. Reutskaya, and I. A. Gorbacheva, Russian Patent 974800; Buyl. Izobr., No. 39–40, 200 (1993).Google Scholar
  15. 15.
    A. A. Akhrem, O. V. Gulyakevich, G. N. Lysenko, A. L. Mikhal’chuk, and G. B. Tolstorozhev, Zh. Prikl. Spektrosk., 68, 427 (2001).Google Scholar
  16. 16.
    A. A. Akhrem, O. V. Gulyakevich, G. N. Lysenko, A. L. Mikhal’chuk, and G. B. Tolstorozhev, Zh. Prikl. Spektrosk., 68, 551 (2001).Google Scholar
  17. 17.
    N. A. Borisevich, O. V. Gulyakevich, A. L. Mikhal’chuk, and I. V. Skornyakov, Zh. Prikl. Spektrosk., 70, 28 (2003).Google Scholar
  18. 18.
    V. Z. Kurbako, Dokl. Akad. Nauk Beloruss. SSR, 34, 716 (1990).Google Scholar
  19. 19.
    V. M. Uelli and T. R. Govindachari, Organic Reactions [Russian translation], Inostr. Lit., Vol. 6, Moscow (1953), p. 98.Google Scholar
  20. 20.
    A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, and R. Spagna, J. Appl. Crystallogr., 32, 115 (1999).Google Scholar
  21. 21.
    G. M. Sheldrick, Program for Crystal Structure Refinement, Göttingen University, Göttingen, Germany (1997).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • O. V. Gulyakevich
    • 1
  • P. V. Kurman
    • 2
  • A. S. Lyakhov
    • 3
  • A. L. Mikhal’chuk
    • 1
  1. 1.State Science Establishment, Institute of Bioorganic ChemistryBelarus National Academy of SciencesMinsk
  2. 2.RTSC “Ecomir”Belorussian Republic Academy of SciencesMinsk
  3. 3.F. Skorina Science Research CenterBelorussian State UniversityMinsk

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