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Chemistry of Heterocyclic Compounds

, Volume 29, Issue 11, pp 1335–1339 | Cite as

Synthesis and some properties of 6-β-oxoalkyl(aralkyl, hetaralkyl, cycloalkyl)thiopurines

  • P. M. Kochergin
  • M. Yu. Gromov
  • E. V. Aleksandrova
  • S. Ya. Skachilova
Article

Abstract

The reaction of 6-purinethione with α-haloketones has given a series of new 6-β-oxoalkyl(aralkyl, hetaralkyl, cycloalkyl)thiopurines. Their alkylation in position 9 and acid hydrolysis to hypoxanthine and its 9-alkyl derivatives has been studied. The hydrolysis of the acetals of 6-formylmethylthiopurine and the oxidation of 6-(2,3-dihydroxypropyl)thiopurine leads to 6-formylmethylthiopurine, which shows a ring-chain tautomerism and exists in the form of 7-hydroxy-7,8-dihydrothiazolo[2,3-i]purine.

Keywords

Oxidation Acetal Hydrolysis Organic Chemistry Alkylation 
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.

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References

  1. 1.
    E. V. Kochergina, A. N. Krasovskii, N. A. Klyuev, and V. A. Zamurenko, Farm. Zh., No. 6, 33 (1981).Google Scholar
  2. 2.
    Patent (USA) 3238207, Chem. Abstr., 64, 15899f (1966).Google Scholar
  3. 3.
    P. M. Kochergin, E. V. Aleksandrova, M. Yu. Gromov, E. V. Popova, R. M. Palei, S. Ya. Skachilova, and E. V. Rusinova, 5th All-Union Conf. on the Chemistry of Nitrogen Heterocyclic Compounds, Abstracts of Papers, Part 1 [in Russian], Chernogolovka (1991), p. 79.Google Scholar
  4. 4.
    P. M. Kochergin, E. V. Aleksandrova, and M. Yu. Gromova, Chem. Geterotsikl. Soedin., No. 10, 1435 (1993).Google Scholar
  5. 5.
    W. G. Coburn, M. C. Thorpe, and J. A. Montgomery, J. Org. Chem., 4, 1114 (1965).Google Scholar
  6. 6.
    R. Robins, E. Godefroi, E. C. Taylor, L. R. Lewis, and A. Jackson, J. Am. Chem. Soc., 83, 2574 (1961).Google Scholar
  7. 7.
    W. Gazine, J. Pol. Chem., 55, 1157 (1981).Google Scholar
  8. 8.
    A. N. Krasovskii and P. M. Kochergin, 1st Moscow Conf. on Organic Chemistry and Technology, Abstracts of Papers [in Russian], Moscow (1976), p. 55.Google Scholar
  9. 9.
    P. M. Kochergin, Zh. Obshch. Khim., 26, 2905 (1956).Google Scholar
  10. 10.
    P. M. Kochergin, A. M. Tsyganova, and L. M. Viktorova, Khim. Geterotsikl. Soedin., No. 1, 93 (1967).Google Scholar
  11. 11.
    L. M. Alekseeva, E. I. Peresleni, Yu. N. Sheinker, P. M. Kochergin, A. N. Krasovskii, and B. V. Kurmaz, Khim. Geterotsikl. Soedin., No. 8, 1125 (1972).Google Scholar
  12. 12.
    T. P. Johnston, L. B. Holum, and J. A. Montgomery, J. Am. Chem. Soc., 80, 6265 (1958).Google Scholar
  13. 13.
    G. H. Lister (ed.), Fused Pyrimidines. Part 2. Purines, Wiley Interscience, New York-Sydney (1971), p. 546.Google Scholar
  14. 14.
    E. Fischer, Ber., 31, 114 (1898).Google Scholar
  15. 15.
    J. A. Montgomery and G. Temple, J. Am. Chem. Soc., 79, 5238 (1957).Google Scholar
  16. 16.
    P. Nuhn, E. Schilling, G. Wagner, J. Hemmerling, K. Malberg, H. Stulpner, and H. Ambrosius, Pharmazie, 32, 558 (1977).Google Scholar
  17. 17.
    L. Lewis, C. Noell, and A. Beamen, J. Med. Pharm. Chemical, No. 5, 607 (1962).Google Scholar

Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • P. M. Kochergin
    • 1
    • 2
    • 3
  • M. Yu. Gromov
    • 1
    • 2
    • 3
  • E. V. Aleksandrova
    • 1
    • 2
    • 3
  • S. Ya. Skachilova
    • 1
    • 2
    • 3
  1. 1.Center for Chemistry of DrugsAll-Russian Scientific-Research Chemical and Pharmaceutical InstituteMoscow
  2. 2.All-Russian Scientific Center for the Safety of Biologically Active SubstancesStaraya KupavnaMoscow Region
  3. 3.Zaporozh'e Medical InstituteZaporozh'e

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