Skip to main content
Log in

Synthesis of partially hydrogenated pyrazolo[3,4-b]quinolinones by condensation of 3-amino-5-methylpyrazole with aromatic aldehydes and dimedone

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Cyclocondensation of 3-amino-5-methylpyrazole with 2-arylmethylidene-5,5-dimethylcyclohexane-1,3-diones or 9-aryl-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-diones, as well as with synthetic precursors of the latter (para-substituted benzaldehydes and dimedone), in dimethylformamide or methanol gives the corresponding 4-aryl-3,7,7-trimethyl-2,4,6,7,8,9-hexahydropyrazolo[3,4-b]quinolin-5-ones. The structure of 4-(4-methoxyphenyl)-3,7,7-trimethyl-2,4,6,7,8,9-hexahydropyrazolo[3,4-b]quinolin-5-one was proved by the X-ray diffraction data.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Bossert, F. and Vater, W., Med. Res. Rev., 1989, vol. 9, p. 291.

    CAS  Google Scholar 

  2. Alajarin, R., Alvarez-Builla, J., Vaquero, J.J., Sunkel, C., Fau de Casa-Juanna, M., Statkow, P.R., and Sanz-Aparicio, J., Tetrahedron: Asymmetry, 1993, vol. 4, p. 617.

    Article  CAS  Google Scholar 

  3. Orlov, V.D., Desenko, S.M., Potekhin, K.A., and Struchkov, Yu.T., Khim. Geterotsikl. Soedin., 1988, p. 229.

  4. Desenko, S.M., Orlov, V.D., and Estrada, Kh., Khim. Geterotsikl. Soedin., 1990, p. 999.

  5. Desenko, S.M., Orlov, V.D., Estrada, Kh., and Ponomarev, L.A., Khim. Geterotsikl. Soedin., 1991, p. 105.

  6. Desenko, S.M., Orlov, V.D., and Estrada, Kh., Khim. Geterotsikl. Soedin., 1991, p. 694.

  7. Desenko, S.M., Orlov, V.D., Lipson, V.V., Ryndina, E.N., Chuvurin, A.V., Kirichenko, A.A., and Gorbenko, N.I., Khim.-Farm. Zh., 1994, no. 3, p. 19.

  8. Lipson, V.V., Desenko, S.M., Shirobokova, M.G., and Borodina, V.V., Khim. Geterotsikl. Soedin., 2003, p. 1383.

  9. Lipson, V.V., Ignatenko, I.V., Desenko, S.M., Shishkina, S.V., Shishkin, O.V., Komykhov, S.A., Logvinenko, N.V., Orlov, V.D., and Meier, H., J. Heterocycl. Chem., 2003, vol. 40, p. 1081.

    CAS  Google Scholar 

  10. Lipson, V.V., Desenko, S.M., Borodina, V.V., Shirobokova, M.G., and Musatov, V.I., Russ. J. Org. Chem., 2005, vol. 41, p. 114.

    Article  CAS  Google Scholar 

  11. Desenko, S.M., Orlov, V.D., Lipson, V.V., and Estrada, Kh., Khim. Geterotsikl. Soedin., 1991, p. 1215.

  12. Lipson, V.V., Desenko, S.M., Orlov, V.D., Ryndina, E.N., Chuvurin, A.V., Gorbenko, N.I., and Kirichenko, A.A., Khim.-Farm. Zh., 1994, no. 2, p. 14.

  13. El Ella, D.A., Gnitzer, E., and Wendelin, W., J. Heterocycl. Chem., 1996, vol. 33, p. 373.

    Article  Google Scholar 

  14. Lipson, V.V. Desenko, S.M., Shishkina, S.V., Shirobokova, M.G., Shishkin, O.V., and Orlov, V.D., Khim. Geterotsikl. Soedin., 2003, p. 1194.

  15. Orlov, V.D., Kolos, N.N., Quiroga, J., and Desenko, S.M., Khim. Geterotsikl. Soedin., 1988, p. 962.

  16. Desenko, S.M., Orlov, V.D., Lipson, V.V., Shishkin, O.V., Potekhin, K.A., and Struchkov, Yu.T., Khim. Geterotsikl. Soedin., 1993, p. 109.

  17. Lindeman, S.V., Strychkov, Yu.T., Shishkin, O.V., Desenko, S.M., Lipson, V.V., and Orlov, V.D., Acta Crystallogr., Sect. C, 1993, vol. 49, p. 896.

    Article  Google Scholar 

  18. Bellec, C. and Lhommet, G., J. Heterocycl. Chem., 1995, vol. 32, p. 1793.

    CAS  Google Scholar 

  19. Quiroga, J., Hormaza, A., Insuasty, B., Saitz, C., Jullian, C., and Canete, A., J. Heterocycl. Chem., 1998, vol. 35, p. 61.

    CAS  Google Scholar 

  20. Desenko, S.M., Orlov, V.D., Shishkin, O.V., Getmanskii, N.V., Lipson, V.V., Lindeman, S.V., and Struchkov, Yu.T., Khim. Geterotsikl. Soedin., 1993, p. 481.

  21. Quiroga, J., Insuasty, B., Hormaza, A., Gamenara, D., Dominguez, L., and Saldana, J., J. Heterocycl. Chem., 1999, vol. 36, p. 11.

    CAS  Google Scholar 

  22. Desenko, S.M., Orlov, V.D., Lipson, V.V., Lindeman, S.V., and Struchkov, Yu.T., Khim. Geterotskl. Soedin., 1991, p. 1539.

  23. Tsuda, Y.N., Mishina, T., Obata, M., Araki, K., Inui, A., and Nakamura, T., JPN Patent Appl. no. 61-227584, 1986; Chem. Abstr., 1987, vol. 106, no. 176416m.

  24. Tsuda, Y.N., Mishina, T., Obata, M., Araki, K., Inui, A., and Nakamura, T., JPN Patent Appl. no. 63-101383, 1988; Chem. Abstr., 1988, vol. 109, no. 128988g.

  25. Reiter, J. and Esses-Reiter, K., J. Heterocycl. Chem., 1991, vol. 28, p. 561.

    Article  CAS  Google Scholar 

  26. Reiter, J., Berecz, G., and Pallagi, I., J. Heterocycl. Chem., 1991, vol. 28, p. 721.

    CAS  Google Scholar 

  27. Rivo, E. and Reiter, J., J. Heterocycl. Chem., 1992, vol. 29, p. 1189.

    CAS  Google Scholar 

  28. Berecz, G., Reiter, J., and Csaszar, J., J. Heterocycl. Chem., 1999, vol. 36, p. 1199.

    Article  CAS  Google Scholar 

  29. Desenko, S.M., Lipson, V.V., Shishkin, O.V., Komykhov, S.A., Orlov, V.D., Lakin, E.E., Kuznetsov, V.P., and Meier, H., J. Heterocycl, Chem., 1999, vol. 36, p. 205.

    CAS  Google Scholar 

  30. Lipson, V.V., Orlov, V.D., Desenko, S.M., Karnozhitskaya, T.M., and Shirobokova, M.G., Khim. Geterotsikl. Soedin., 1999, p. 664.

  31. Lipson, V.V., Orlov, V.D., Desenko, S.M., Shishkina, S.V., Shishkin, O.V., and Shirobokova, M.G., Khim. Geterotsikl. Soedin., 2000, p. 1190.

  32. Lipson, V.V., Orlov, V.D., Desenko, S.M., Shishkin, O.V., Shirobokova, M.G., Chernenko, V.N., and Zinov’eva, L.I., Khim. Geterotsikl. Soedin., 2000, p. 1542.

  33. Lipson, V.V., Desenko, S.M., Borodina, V.V., Shirobokova, M.G., Karnozhitskaya, T.M., Musatov, V.I., and Kravchenko, S.V., Khim. Geterotsikl. Soedin., 2005, p. 246.

  34. Lipson, V.V., Borodina, V.V., Bozhko, T.S., Ladogubets, E.V., and Rozhovetskaya, I.A., Ukrainian Patent no. 68302A, 2004; Ukr. Pat. Byul., 2004, p. 7.

  35. Zefirov, N.S., Palyulin, V.A., and Dashevskaya, E.E., J. Phys. Org. Chem., 1990, vol. 3, p. 147.

    Article  CAS  Google Scholar 

  36. Zefirov, Yu.V. and Zorkii, P.M., Usp. Khim., 1989, vol. 58, p. 713.

    CAS  Google Scholar 

  37. Burgi, H.-B. and Dunitz, J.D., Structure Correlation, Weinheim: VCH, 1994, vol. 2, p. 741.

    Google Scholar 

  38. Margaretha, P. and Polansky, O.E., Monatsh. Chem., 1970, vol. 101, p. 824.

    Article  CAS  Google Scholar 

  39. Zitsmanie, A.Kh., Klyavin’sh, M.K., and Roska, A.S., Izv. Akad. Nauk Latv. SSR, 1988, no. 1, p. 91.

  40. Handbook of Chemistry and Physics, Lide, D.R., Ed., London: CRC, 1994, pp. 3–122.

    Google Scholar 

  41. Sheldrick, G.M., SHELX97. PC Version. Rev. 2, 1998.

Download references

Author information

Authors and Affiliations

Authors

Additional information

Original Russian Text © V.V. Lipson, M.G. Shirobokova, O.V. Shishkin, S.V. Shishkina, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 7, pp. 1034–1039.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lipson, V.V., Shirobokova, M.G., Shishkin, O.V. et al. Synthesis of partially hydrogenated pyrazolo[3,4-b]quinolinones by condensation of 3-amino-5-methylpyrazole with aromatic aldehydes and dimedone. Russ J Org Chem 42, 1015–1021 (2006). https://doi.org/10.1134/S1070428006070141

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428006070141

Keywords

Navigation