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Chemistry of Heterocyclic Compounds

, Volume 33, Issue 12, pp 1450–1455 | Cite as

Synthesis of pyrrolopyrimidines from 2,5-diaryl-3,3,4,4-tetracyanopyrrolidines

  • O. E. Nasakin
  • A. N. Lyshchikov
  • P. M. Lukin
  • V. A. Tafeenko
  • A. Kh. Bulai
Article

Abstract

Feasibility has been demonstrated for the synthesis of pyrrolo[1,2-a]pyrimidines by the reaction of 2,5-diaryl-3,3,4,4-tetracyanopyrrolidines I with β-dicarbonyl compounds, which was carried out by the rearrangement of I to give 2-(N-arylidenamino)-5-aryl-3,4-dicaynopyrroles II. A different pathway was found for the reaction of pyrroles II with β-diketones and ethyl acetoacetate. The existence of a latento-enaminonitrile fragment in these compounds permits their conversion to pyrrolo[2,3-d]pyrimidines.

Keywords

Ethyl Organic Chemistry Pyrimidine Pyrrole Acetoacetate 
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.
    O. E. Nasakin, A. N. Lyshchikov, P. M. Lukin, and A. Kh. Bulai, Khim. Geterotsikl. Soedin., No. 3, 353 (1994).Google Scholar
  2. 2.
    V. I. Shvedov, M. V. Mezentseva, A. N. Grinev, and A. I. Ermakov, Khim. Geterotsikl. Soedin., No. 12, 1677 (1976).Google Scholar
  3. 3.
    H. Wamhoff and B. Wehling, Chem. Ber.109, No. 9, 2983 (1976).Google Scholar
  4. 4.
    O. E. Nasakin, A. N. Lyshchikov, P. M. Lukin, and A. Kh. Bulai, Khim. Geterotsikl. Soedin., No. 1, 42 (1995).Google Scholar
  5. 5.
    O. E. Nasakin A. N. Lyshchikin, P. M. Lukin, A. Kh. Bulai, B. A. Tafeenko, and P. A. Sharbatyan, Khim. Geterotsikl. Soedin., No. 11, 1502 (1991).Google Scholar
  6. 6.
    O. E. Nasakin, A. N. Lyshchikov, P. M. Lukin, and B. A. Tafeenko, Khim. Geterotsikl. Soedin., No. 11, 1472 (1992).Google Scholar
  7. 7.
    C. W. Smith, D. G. Norton, and S. A. Ballard, J. Am. Chem. Soc.,87, 1995 (1965).Google Scholar
  8. 8.
    R. L. Tolman, R. K. Robins, and L. B. Townsend, J. Am. Chem. Soc.,91, 2102 (1969).Google Scholar

Copyright information

© Plenum Publishing Publishing Corporation 1998

Authors and Affiliations

  • O. E. Nasakin
  • A. N. Lyshchikov
  • P. M. Lukin
  • V. A. Tafeenko
  • A. Kh. Bulai

There are no affiliations available

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