Skip to main content
SpringerLink
Log in

Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one derivatives

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

Abstract

Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one and its N-methyl derivatives at 0–5°C and 60°C gives 5-nitro-and 5,6-dinitro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones, respectively. The latter can also be obtained by nitration of 5-mononitro derivatives under similar conditions. The nitration of 6-chloro-and 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones and their N-methyl-substituted analogs leads to the formation of the corresponding 6-chloro(bromo)-5-nitro compounds. The same products are formed in the nitration of 5,6-dichloro-and 5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones. In this case, the process involves replacement of the halogen atom in position 5 of the pyridine fragment by nitro group. The nitration of 6-bromo-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one is accompanied by oxidation of the 5-methyl group to carboxy.

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. Yutilov, Yu.M. and Khabarov, K.M., USSR Inventor’s Certificate no. 891 671, 1981; Byull. Izobret., 1981, no. 47; Yutilov, Yu.M. and Khabarov, K.M., Khim. Geterotsikl. Soedin., 1986, p. 227; Yutilov, Yu.M., Khabarov, K.M., Komissarov, I.V., and Filippov, I.T., USSR Inventor’s Certificate no. 1 048 746, 1987; Byull. Izobret., 1987, no. 47; Yutilov, Yu.M., Khabarov, K.M., Filippov, I.T., and Komissarov, I.V., USSR Inventor’s Certificate no. 991716, 1987; Byull. Izobret., 1987, no. 48; Yutilov, Yu.M., Khabarov, K.M., Filippov, I.T., Komissarov, I.V., and Svertilova, I.A., USSR Inventor’s Certificate no. 1094303, 1987; Byull. Izobret., 1987, no. 48; Yutilov, Yu.M., Khabarov, K.M., Orestenko, L.P., and Kirichenko, V.V., USSR Inventor’s Certificate no. 1048745, 1983; Byull. Izobret., 1997, no. 29; Yutilov, Yu.M., Komissarov, I.V., Khabarov, K.M., and Filippov, I.T., USSR Inventor’s Certificate no. 1010846, 1983; Byull. Izobret., 1997, no. 34; Yutilov, Yu.M., Khabarov, K.M., and Galitsina, V.V., USSR Inventor’s Certificate no. 860463, 1998; Byull. Izobret., 1998, no. 15; Shcherbina, L.I. and Yutilov, Yu.M., Ukr. Khim. Zh., 2002, vol. 68, p. 114.

  2. Bystrova, R.M., Cand. Sci. (Chem.) Dissertation, Donetsk, 1973.

  3. Jaine, P.C., Chatterjee, S.K., and Anand, N., J. Chem. Soc., 1966, p. 403.

  4. Yutilov, Yu.M. and Bystrova, R.M., Khim. Geterotsikl. Soedin., 1968, p. 953.

  5. Yutilov, Yu.M., Bystrova, R.M., and Svertilova, I.A., Abstracts of Papers, XII Ukrainskaya respublikanskaya konferentsiya po organicheskoi khimii (XIIth Ukrainian Republican Conf. on Organic Chemistry), Uzhgorod, 1974, p. 120.

  6. Yutilov, Yu.M., Advances in Heterocyclic Chemistry, Katritzky, A.R., Ed., New York: Academic, 2005, vol. 89, p. 161.

    Google Scholar 

  7. Bystrova, R.M. and Yutilov, Yu.M., Khim. Geterotsikl. Soedin., 1969, p. 378.

  8. Brooks, W. and Day, A.R., J. Heterocycl. Chem., 1969, vol. 6, p. 759.

    Article  CAS  Google Scholar 

  9. Clark-Levis, I.W. and Thompson, M.I., J. Chem. Soc., 1957, p. 442; Yutilov, Yu.M. and Svertilova, I.A., Khim. Geterotsikl. Soedin., 1976, p. 1252.

  10. Vaughan, J.R., Jr., Krapcho, J., and English, J.P., J. Am. Chem. Soc., 1949, vol. 71, p. 1885; Petrov, V. and Saper, J., J. Chem. Soc., 1948, p. 1389; Yutilov, Yu.M., Malyutina, V.F., Lopatinskaya, Kh.Ya., and Svertilova, I.A., Russ. J. Org. Chem., 1998, vol. 34, p. 1363; Yutilov, Yu.M., Lopatinskaya, Kh.Ya., Smolyar, N.N., and Korol’, I.V., Ukr. Khim. Zh., 2003, vol. 69, p. 62; Yutilov, Yu.M., Lopatinskaya, Kh.Ya., Smolyar, N.N., and Korol’, I.V., Russ. J. Org. Chem., 2003, vol. 39, p. 280; Grivas, S. and Lindstrom, S., J. Heterocycl. Chem., 1995, vol. 32, p. 467; Israel, M. and Day, A.R., J. Org. Chem., 1959, vol. 24, p. 1455; Yutilov, Yu.M., Lopatinskaya, Kh.Ya., Smolyar, N.N., and Gres’ko, S.V., Russ. J. Org. Chem., 2005, vol. 41, p. 450; Yutilov, Yu.M., Lopatinskaya, Kh.Ya., Smolyar, N.N., and Gres’ko, S.V., Russ. J. Org. Chem., 2005, vol. 41, p. 575.

    Article  CAS  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, Kh. Ya. Lopatinskaya, A. B. Vasilechko, 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. Kh. Ya. Lopatinskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. B. Vasilechko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. A. Lomov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. 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, Kh.Ya. Lopatinskaya, A.B. Vasilechko, D.A. Lomov, Yu.M. Yutilov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 3, pp. 418–422.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Smolyar, N.N., Lopatinskaya, K.Y., Vasilechko, A.B. et al. Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one derivatives. Russ J Org Chem 43, 417–421 (2007). https://doi.org/10.1134/S1070428007030153

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428007030153

Keywords

Search

Navigation