Skip to main content
SpringerLink
Log in

Synthesis of 2-hetarylimidazo[4,5-d]pyridazine derivatives

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

Abstract

2-Chloropyridine-3,4-diamine reacted with hetarenecarboxylic acids (pyridine-2-, pyridine-3-, and pyridine-4-carboxylic acids and 6-oxo-1,6-dihydropyridazine-3-carboxylic acid) in polyphosphoric acid at 160–170°C to give the corresponding 2-hetarylimidazo[4,5-c]pyridin-4-ones. Nitration of the latter with a mixture of concentrated nitric and sulfuric acids led to the formation of 2-hetaryl-7-nitroimidazo[4,5-c]pyridin-4-ones which were converted into 2-hetaryl-7-methylimidazo[4,5-d]pyridazin-4-ones by the action of hydrazine hydrate at 140–150°C.

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

Access this article

Log in via an institution

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. Gerhardt, G.A., Aldous, D.L., and Castle, R.N., J. Heterocycl. Chem., 1965, vol. 2, p. 247.

    CAS  Google Scholar 

  2. Austel, V., Heider, J., Hauel, N., Reiffen, M., Nickl, J., Meel, J., and Dideren, W., FRG Patent Appl. no. 3347290, 1985; Ref. Zh., Khim., 1986, no. 13O79P.

  3. Heider, J., Hauel, N., Austel, V., Meel, J., and Dideren, W., FRG Patent Appl. no. 3445299, 1986; Ref. Zh., Khim., 1987, no. 3O147P.

  4. Itai, T. and Suzuki, S., Chem. Pharm. Bull., 1960, vol. 8, p. 999.

    CAS  Google Scholar 

  5. Yanai, M., Kinoshita, T., Takeda, O., Sadaki, H., and Watanabe, H., Chem. Pharm. Bull., 1970, vol. 18, p. 1685.

    CAS  Google Scholar 

  6. Kenji, K., Hiromu, N., Yusho, O., Keizo, T., and Hirohisa, O., J. Heterocycl. Chem., 1984, vol. 21, p. 1249.

    Google Scholar 

  7. Gres’ko, S.V., Smolyar, N.N., and Yutilov, Yu.M., Russ. J. Org. Chem., 2001, vol. 37, p. 1026.

    Article  CAS  Google Scholar 

  8. Yutilov, Yu.M. and Svertilova, I.A., Khim. Geterotsikl. Soedin., 1982, p. 705; Yutilov, Yu.M. and Smolyar, N.N., Khim. Geterotsikl. Soedin., 1984, p. 132; Yutilov, Yu.M. and Smolyar, N.N., Zh. Org. Khim., 1986, vol. 22, p. 1793; Yutilov, Yu.M., Smolyar, N.N., and Gres’ko, S.V., Russ. J. Org. Chem., 1995, vol. 31, p. 273; Yutilov, Yu.M. and Svertilova, I.A., Russ. J. Org. Chem., 1999, vol. 35, p. 583; Gres’ko, S.V., Smolyar, N.N., and Yutilov, Yu.M., Ukr. Khim. Zh., 2003, vol. 69, p. 110; Yutilov, Yu.M., Smolyar, N.N., Eres’ko, A.B., and Gres’ko, S.V., Russ. J. Org. Chem., 2004, vol. 40, p. 1015.

  9. Yutilov, Yu.M. and Svertilova, I.A., Russ. J. Org. Chem., 1999, vol. 35, p. 451.

    CAS  Google Scholar 

  10. Sing, B., Heterocycles, 1984, vol. 22, p. 1801.

    Article  Google Scholar 

  11. Yutilov, Yu.M. and Svertilova, I.A., USSR Inventor’s Certificate no. 1187438, 1985; Byull. Izobret., 1987, no. 29.

  12. Bremer, O., Justus Liebigs Ann. Chem., 1939, vol. 539, p. 276; Koenigs, E., Milds, M., and Gurlt, H., Chem. Ber., 1924, vol. 57, p. 1179; Stetsenko, L.V. and Miroshnichenko, N.S., Ukr. Khim. Zh., 1973, vol. 49, p. 703; Svertilova, I.A., Smolyar, N.N., and Yutilov, Yu.M., Ukr. Khim. Zh., 1986, vol. 62, p. 64.

    CAS  Google Scholar 

  13. Gabriel, S., Chem. Ber., 1909, vol. 42, p. 655.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, ul. R. Lyuksemburg 70, Donetsk, 83114, Ukraine

    N. N. Smolyar, D. A. Lomov & Yu. M. Yutilov

Authors
  1. N. N. Smolyar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. A. Lomov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. M. Yutilov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © N.N. Smolyar, D.A. Lomov, Yu.M. Yutilov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 6, pp. 898–901.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Smolyar, N.N., Lomov, D.A. & Yutilov, Y.M. Synthesis of 2-hetarylimidazo[4,5-d]pyridazine derivatives. Russ J Org Chem 43, 897–900 (2007). https://doi.org/10.1134/S1070428007060164

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428007060164

Keywords

Search

Navigation