Skip to main content
SpringerLink
Log in

Oxidation of 4,7-phenanthroline derivatives

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

Abstract

Oxidation of 1,3-diphenyl-4,7-phenanthroline with potassium permanganate in alkaline medium results in transformation of the 4,7-phenanthroline ring system into 1,8-diaazafluorenone. Oxidation of 12-aryl-and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-ones (condensation products of 6-arylmethylene-aminoquinolines with 1,3-cyclohexanedione and dimedone) with sodium nitrite in acetic acid leads to 12-aryl-9,10-dihydro-8H-benzo[b][4,7]phenanthrolin-11-ones. 13-Aryl-7,13-dihydro-12H-indeno-[2,1-b][4,7]phenanthrolin-12-ones obtained by reaction of 6-arylmethyleneaminoquinolines with 1,3-indandione are oxidized to 13-aryl-12H-indeno[2,1-b][4,7]phenanthrolin-12-ones on heating in nitrobenzene.

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. Smith, C.R., J. Am. Chem. Soc., 1930, vol. 52, p. 397.

    Google Scholar 

  2. Kabachnik, M.I. and Rezon, V.V., Zh. Prikl. Khim., 1936, vol. 9, p. 2026.

    Google Scholar 

  3. Husseini, R. and Stretton, R.J., Microbios, 1981, vol. 30, p. 7.

    Google Scholar 

  4. Bailenger, J., Therapie, 1961, vol. 16, p. 287; Chem. Abstr., 1964, vol. 60, p. 2222 z.

    Google Scholar 

  5. Mashkovskii, M.D., Lekarstvennye veshchestva (Drugs), Khar’kov: Torsing, 1998, vol. 2, p. 313.

    Google Scholar 

  6. FRG Patent no. 1 232 156, 1967; Chem. Abstr., 1967, vol. 66, p. 115 700 b.

  7. Fr. Patent no. 1 369 625, 1964; Chem. Abstr., 1965, vol. 62, p. 1664 i.

  8. Fr. Patent no. 1 382 542, 1964; Chem. Abstr., 1965, vol. 63, p. 7912 a.

  9. Kozlov, N.S., Gusak, K.N., Serzhanina, V.A., and Krot, N.A., Khim. Geterotsikl. Soedin., 1985, p. 1398.

  10. Eckhard, J.F. and Summers, L.A., Aust. J. Chem., 1973, vol. 26, p. 2727.

    Google Scholar 

  11. Klock, K., Mlochowski, J., and Szulc, Z., J. Prakt. Chem., 1977, vol. 319, p. 959.

    Google Scholar 

  12. Diesveld, J.W., Borkent, J.H., and Laarhoven, W.H., Tetrahedron, 1982, vol. 38, p. 1803.

    Google Scholar 

  13. Mlochowski, J. and Skrowarczewska, Z., Roczn. Chem., 1973, vol. 47, p. 2255.

    Google Scholar 

  14. Martinez, R., Cortes, E., and Toscano, R.A., J. Heterocycl. Chem., 1990, vol. 27, p. 363.

    Google Scholar 

  15. Kozlov, N.S., Gusak, K.N., and Serzhanina, V.A., Dokl. Akad. Nauk SSSR, 1986, vol. 287, p. 1142.

    Google Scholar 

  16. Kozlov, N.S., 5,6-Benzokhinoliny (5,6-Benzoquinolines), Minsk: Nauka i Tekhnika, 1970, p. 96.

    Google Scholar 

  17. Neiland, O., Tsiklicheskie β-diketony (Cyclic β-Diketones), Riga: Akad. Nauk Latv. SSR, 1961, p. 155.

    Google Scholar 

  18. Kozlov, N.S., Pak, V.D., and Nugumanov, Z.Z., Khim. Geterotsikl. Soedin., 1970, p. 194.

Download references

Author information

Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, 220072, Minsk, Belarus

    K. N. Gusak, N. G. Kozlov & A. B. Tereshko

Authors
  1. K. N. Gusak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. G. Kozlov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. B. Tereshko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 9, 2004, pp. 1369–1375.

Original Russian Text Copyright © 2004 by Gusak, Kozlov, Tereshko.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gusak, K.N., Kozlov, N.G. & Tereshko, A.B. Oxidation of 4,7-phenanthroline derivatives. Russ J Org Chem 40, 1322–1328 (2004). https://doi.org/10.1007/s11178-005-0014-4

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0014-4

Keywords

Search

Navigation