Pharmaceutical Chemistry Journal

, Volume 1, Issue 5, pp 247–250 | Cite as

Lactams IX. A new approach to the synthesis of 5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidines

  • V. G. Granik
  • R. G. Glushkov
Article
  • 24 Downloads

Abstract

A new method for the synthesis of derivatives of pyrrolo[2,3-d]pyrimidine has been developed, including the ethylation of 3-carboethoxy-2-pyrrolidone with triethyloxonium fluoborate and the condensation of 2-ethoxy-3-carboethoxy-1,2-dihydropyrrolidine with compounds of the general formula R-C(=NH)NH2, where R is NH2, SH, OH, SCH3, or CH3.

Keywords

Organic Chemistry Pyrimidine General Formula Lactam Fluoborate 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    Yu. P. Shvachkin, Uspekhi Khimii,26, No. 7, p. 824 (1957).Google Scholar
  2. 2.
    E. C. Taylor and R. W. Hendness, J. Am. Chem.Soc.,86, p. 951 (1964).Google Scholar
  3. 3.
    Idem, Ibid.,87, p. 1995 (1965).Google Scholar
  4. 4.
    K. Ansai, G. Nakamura, and S. J. Suzuki, Antibiot. (Tokyo),10A, p. 201 (1957).Google Scholar
  5. 5.
    S. Suzuki and S. Marumo, Ibid.,12 A, p. 360 (1960).Google Scholar
  6. 6.
    Idem, Ibid., 14A, p. 34 (1961).Google Scholar
  7. 7.
    Y. Mizuno, M. Ikehara, K. Watanabe, et al., Chem. Pharm. Bull.,11, p. 1093 (1963).Google Scholar
  8. 8.
    Y. Mizuno, M. Ikehara, K. A. Watanabe, et al., J. Org. Chem.,28, p. 3329 (1963).Google Scholar
  9. 9.
    H. Nishimura, K. Katagiri, K. Sato, et al., J. Antibiot. (Tokyo),9A, p. 60 (1956).Google Scholar
  10. 10.
    K. Ohkuma, Ibid.,14A, p. 343 (1961).Google Scholar
  11. 11.
    Idem, Ibid.,13A, p. 361 (1960).Google Scholar
  12. 12.
    Brit. Patent No. 812366, 1959; Chem. Abstr.,54, p. 592 (1960).Google Scholar
  13. 13.
    J. Davoll, J. Chem. Soc.,131 (1960).Google Scholar
  14. 14.
    J. Kopecky and J. Michl, Czech. Patent No. 97821 (1960).Google Scholar
  15. 15.
    L. Schuler and L. Suranyi, Ger. Patent, No. 1109698 (1959); Chem. Abstr.,56, p. 8727b (1962).Google Scholar
  16. 16.
    Idem, Germ. Patent No. 1100030 (1961); Chem. Abstr.,55, p. 27381h (1961).Google Scholar
  17. 17.
    Johnson and Kohmann, Am. Chem. J.,49, p. 186 (1913).Google Scholar
  18. 18.
    P. Nesbitt and P. Sykes, J. Chem.Soc., p. 3057 (1954).Google Scholar
  19. 19.
    Z. Foldi, G. Fodor, I. Demjen, et al., Ber. Dtsch. Chem. Ges.,75B, 755 (1942).Google Scholar
  20. 20.
    J. Biggs and P. Sykes, J.Chem. Soc., p. 1849 (1959).Google Scholar
  21. 21.
    C. Wayne and R. K. Robins, J. Heterocycl. Chem.,1, No. 1, p. 34 (1964).Google Scholar
  22. 22.
    S. Petersen and E. Tietze, Justus Liebigs Ann. Chem.,623, 166 (1959).Google Scholar
  23. 23.
    R. G. Glushkov and O. Yu. Magidson, Zh. Obshchei Khimii,31, p. 1907 (1961).Google Scholar
  24. 24.
    Idem, Khimiya Geterotsikl. Soedinenii, No. 2, p. 240 (1965).Google Scholar
  25. 25.
    J. Kato, H. Jshihara, and O. Hiwataschi, J. Agr. Chem. Soc. Japan,27, p. 498 (1953); Chem. Abstr.,49, p. 30061 (1955).Google Scholar
  26. 26.
    H. Meerwein, E. Battenberg, H. Gold, et al., J. Prakt. Chem.,154, 83 (1939).Google Scholar
  27. 27.
    A. Schrage and G. Hitchings, J. Org. Chem.,16, p. 1153 (1951).Google Scholar
  28. 28.
    R. H. Hammer, J. Pharm. Sci.,54, p. 1826 (1965).Google Scholar
  29. 29.
    R. West, J. Org. Chem.,28, p. 1991 (1963).Google Scholar
  30. 30.
    E. C. Taylor and W. R. Sherman, J. Am. Chem. Soc.,81, p. 2464 (1959).Google Scholar
  31. 31.
    L. N. Yakhontov, M. Ya. Uritskaya, and M. V. Rubtsov, Zh. Obshchei Khimii,34, p. 1449 (1964).Google Scholar

Copyright information

© Consultants Bureau 1968

Authors and Affiliations

  • V. G. Granik
    • 1
  • R. G. Glushkov
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical ChemistryMoscow

Personalised recommendations