Russian Journal of Organic Chemistry

, Volume 43, Issue 11, pp 1686–1695 | Cite as

Synthesis and fluorescence of anthra[2,3-b]furan-5,10-dione derivatives

  • A. E. Shchekotikhin
  • E. K. Shevtsova
  • V. F. Traven’
Article

Abstract

4,11-Dialkoxyanthra[2,3-b]furan-5,10-diones containing various substituents in the 3-position were synthesized. Reactions of these compounds with primary and secondary amines resulted in nucleophilic replacement of one or two alkoxy groups by the corresponding amine residues. 4,11-Dialkoxy derivatives of anthra[2,3-b]furan-5,10-dione showed fluorescence with large Stokes shifts (170–200 nm).

Keywords

Yellow Crystal Oxadiazole Stokes Shift Ethyl Iodide Benzohydrazide 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Haugland, R.P., Handbook of Fluorescent Probes and Research Chemicals, Spence, M.T.Z. and Johnson, I.D., Eds., Eugene, OR, USA: Molecular Probes, 1996, 6th ed., p. 545.Google Scholar
  2. 2.
    Irie, M., Chem. Rev., 2000, vol. 100, p. 1685.CrossRefGoogle Scholar
  3. 3.
    Krasovitskii, B.M. and Bolotin, B.M., Organicheskie lyuminofory (Organic Luminophores), Moscow: Khimiya, 1984, p. 136.Google Scholar
  4. 4.
    Gorelik, M.V., Khimiya antrakhinonov i ikh proizvodnykh (Chemistry of Anthraquinones and Their Derivatives), Moscow: Khimiya, 1983, p. 218.Google Scholar
  5. 5.
    Radanov, S. and Pavlov, P., Sud.-Med. Ekspert., 1976, vol. 19, p. 34.Google Scholar
  6. 6.
    Fischer-Reimann, E., EP patent no. 592366, 1993; Chem. Abstr., 1994, vol. 121, no. 108509b.Google Scholar
  7. 7.
    Shchekotikhin, A.E., Luzikov, Yu.N., Anisimova, O.S., Buyanov, V.N., and Preobrazhenskaya, M.N., Khim. Geterotsikl. Soedin., 2006, p. 691.Google Scholar
  8. 8.
    Patony, G., Salon, J., Sowell, J., and Strekowski, L., Molecules, 2004, vol. 9, p. 41.Google Scholar
  9. 9.
    Allevi, P., Anastasia, M., Ciuffreda, P., Fiecchi, A., and Scala, A., J. Org. Chem., 1987, vol. 52, p. 5469.CrossRefGoogle Scholar
  10. 10.
    Townsend, C.A., Isomura, Y., Davis, S.G., and Hodge, J.A., Tetrahedron, 1989, vol. 45, p. 2263.CrossRefGoogle Scholar
  11. 11.
    Gorelik, M.V. and Mishina, E.V., Zh. Org. Khim., 1983, vol. 19, p. 2185.Google Scholar
  12. 12.
    Suzuki, F., Trenbeath, S., Gleim, R.J., and Sih, C.J., J. Org. Chem., 1978, vol. 43, p. 4159.CrossRefGoogle Scholar
  13. 13.
    Appel, R., Kleinstuk, R., and Ziehn, K.-D., Chem. Ber., 1971, vol. 104, p. 1030.CrossRefGoogle Scholar
  14. 14.
    Lysova, I.V. and Krasovitskii, B.M., Stsintillyatory i organicheskie lyuminofory (Scintillators and Organic Luminophores), Khar’kov, 1975, p. 34.Google Scholar
  15. 15.
    Krasovitskii, B.M. and Afanasiadi, L.M., Preparativnaya khimiya organicheskikh lyuminoforov (Preparative Chemistry of Organic Luminophores), Khar’kov: Folio, 1997, pp. 105, 109, 113.Google Scholar
  16. 16.
    Jones, G.B. and Chapman, B.J., J. Org. Chem., 1993, vol. 58, p. 5558.CrossRefGoogle Scholar
  17. 17.
    Naiki, K., Cho, E., and Tsuruoka, S., J. Synth. Org. Chem., 1959, vol. 17, p. 705.Google Scholar
  18. 18.
    Krapcho, A.P., Shaw, K.J., Landi, J.J., Jr., and Phinney, D.J., J. Org. Chem., 1984, vol. 49, p. 5253.CrossRefGoogle Scholar
  19. 19.
    Shchekotikhin, A.E., Luzikov, Yu.N., Buyanov, V.N., and Preobrazhenskaya, M.N., Khim. Geterotsikl. Soedin., 2006, p. 854.Google Scholar
  20. 20.
    Fain, V.Ya., Elektronnye spektry pogloshcheniya i stroenie antrakhinonov. Dizameshchennye 9,10-antrakhinony (Electronic Absorption Spectra and Structure of Anthraquinones. Disubstituted 9,10-Anthraquinones), Moscow: Sputnik+, 2003, vol. 2, p. 104.Google Scholar
  21. 21.
    Stepanov, B.I., Vvedenie v khimiyu i tekhnologiyu organicheskikh krasitelei (An Introduction to Chemistry and Technology of Organic Dyes), Moscow: Khimiya, 1983, p. 147.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • A. E. Shchekotikhin
    • 1
  • E. K. Shevtsova
    • 1
  • V. F. Traven’
    • 1
  1. 1.Mendeleev Russian University of Chemical TechnologyMoscowRussia

Personalised recommendations