Advertisement

Chemistry of Heterocyclic Compounds

, Volume 48, Issue 2, pp 368–371 | Cite as

Ethyl 5-amino-3-oxo-1,2-dihydro-1H-pyrazole-1-carboxylate in the selective synthesis of partially hydrogenated pyrazolo[3,4-b]pyridin-3-ones

  • P. S. Lebedˈ
  • N. G. Mozgovaya
  • P. O. Kos
  • M. V. Vovk
Article

Ethyl 5-amino-3-oxo-1,2-dihydro-1H-pyrazole-1-carboxylate undergoes selective cyclocondensation with 1,3-dicarbonyl compounds or their synthetic equivalents to give ethyl 3-oxo-1,2-dihydro-pyrazolo[3,4-b]pyridine-1-carboxylates which are readily converted to their 1-unsubstituted analogs.

Keywords

5-amino-1-ethoxycarbonyl-1,2-dihydro-1H-pyrazol-3-one 5-aminopyrazol-3-one 1,3-di-carbonyl compounds pyrazolo[3,4-b]pyridin-3-ones cyclocondensation 

References

  1. 1.
    E. G. Paronikyan, S. N. Sirikanyan, A. S. Noravyan, R. G. Paronikyan, and I. A. Dzhagatspanyan, Khim.-Farm. Zh., 35, No. 1, 9 (2001).Google Scholar
  2. 2.
    R. M. Schelkun and P.-W. Yuen, US Pat. Appl. 2006116376.Google Scholar
  3. 3.
    M. Manpadi, P. Y. Uglinskii, S. K. Rastogi, K. M. Cotter, Y.-S. C. Wong, L. A. Anderson, A. J. Ortega, S. Slambrouck, W. F. A. Steelant, S. Rogelj, P. Tongwa, M. Y. Antipin, I. V. Magedov, and A. Kornienko, Org. Biomol. Chem., 5, 3865 (2007).CrossRefGoogle Scholar
  4. 4.
    G. Zoller, S. Petry, G. Muller, H. Heuer, and K.-H. Bar-Inghaus, WO Pat. Appl. 2005073199.Google Scholar
  5. 5.
    G. Zoller, S. Petry, G. Muller, H. Heuer, and K.-H. N. Tennagels, US Pat. Appl, 2008287448.Google Scholar
  6. 6.
    A. Chandra Sheker Reddy, B. Narsaiah, and R. V. Venkataratnam, Synth. Commun., 27, 2217 (1997).CrossRefGoogle Scholar
  7. 7.
    Z. A. Kalme, B. Roloff, Yu. E. Pelcher, Yu. Yu. Popelis, F. Hagen, and G. J. Duburs, Khim. Geterotsikl. Soedin., 1218 (1992). [Chem. Heterocycl. Compd., 28, 1031 (1992)].Google Scholar
  8. 8.
    R. Balicki, Pol. J. Chem., 57, 1251 (1983).Google Scholar
  9. 9.
    P. Papini, S. Checchi, and M. Ridi, Gazz. Chim. Ital., 87, 931 (1957).Google Scholar
  10. 10.
    J.-L. Imbach, R. Jacquier, and J.-L. Vidal, Bull. Soc. Chim. Fr., 1929 (1970).Google Scholar
  11. 11.
    R. Balicki and P. Nantka-Nemirski, Pol. J. Chem., 54, 2175 (1980).Google Scholar
  12. 12.
    E. C. Taylor and J. W. Barton, J. Am. Chem. Soc., 81, 2448 (1959).CrossRefGoogle Scholar
  13. 13.
    W. Ried and E. U. Kocher, Justus Liebigs Ann. Chem., 647, 116 (1961).CrossRefGoogle Scholar
  14. 14.
    G. Zoller, S. Petry, G. Muller, H. Hever, and K.-H. N. Tennagels, WO Pat. Appl. 2007110216.Google Scholar
  15. 15.
    R. Balicki, Pol. J. Chem., 56, 711 (1982).Google Scholar
  16. 16.
    P. Papini, S. Checchi, and M. Ridi, Gazz. Chim. Ital., 84, 769 (1954).Google Scholar
  17. 17.
    B. Graham, H. D. Porter, and A. Weissberger, J. Am. Chem. Soc., 71, 983 (1949).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • P. S. Lebedˈ
    • 1
  • N. G. Mozgovaya
    • 1
  • P. O. Kos
    • 1
  • M. V. Vovk
    • 1
  1. 1.Institute of Organic ChemistryUkraine National Academy of SciencesKyivUkraine

Personalised recommendations