Chemistry of Heterocyclic Compounds

, Volume 45, Issue 2, pp 151–160 | Cite as

Heterocyclic analogs of 5,12-naphthacenequinone 8.* Synthesis of furano-anthraquinones

  • A. E. ShchekotikhinEmail author
  • Yu. N. Luzikov
  • V. N. Buyanov
  • M. N. Preobrazhenskaya

During the condensation of 2,3-dichloroquinizarine with methyl pivaloylacetate in the presence of potassium carbonate in dimethyl sulfoxide the main reaction products are derivatives of angular 3-pivaloylanthra[1,2-b]furan-2,6,11(3H)-trione (about 70%) and anthra[2,1-d][1,3]dioxole-6,11-dione (15%), whereas the yield of the targeted linear methyl 2-tert-butyl-4,11-dihydroxyanthra[2,3-b]furan-5,10-dione-3-carboxylate is only 2%. Methods are developed for modification of the obtained 3-pivaloylanthra[1,2-b]furan-2,6,11(3H)-trione, making it possible to use it for the synthesis of the tert-butyl derivatives of linear anthra[2,3-b]furan-5,10-dione or angular anthra[1,2-b]furan-6,11-dione.


anthra[2,1-d][1,3]dioxole-6,11-dione anthra[2,3-b]furan-5,10-dione anthra[1,2-b]furan-6,11-dione anthra[1,3-b]furan-2,6,11(3H)-trione 2,3-dichloroquinizarine methyl pivaloylacetate condensation modification 


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  1. 1.
    A. E. Shchekotikhin, Yu. N. Luzikov, Yu. B. Sinkevich, V. N. Buyanov, and M. N. Preobrazhenskaya, Khim. Geterotsikl. Soedin., 1532 (2008). [Chem. Heterocycl. Comp., 44, 1245 (2008)].Google Scholar
  2. 2.
    C. A. Townsend, Y. Isomura, S. G. Davis, and J. A. Hodge, Tetrahedron, 45, 2263 (1989).CrossRefGoogle Scholar
  3. 3.
    M. V. Gorelik and E. V. Mishina, Zh. Org. Khim., 19, 2185 (1983).Google Scholar
  4. 4.
    V. Ya. Fain, Electronic Absorption Spectra and Structure of Anthraquinones [in Russian], Sputnik+ (2003), Vol. 1, 9,10-Anthraquinone and its Monosubstituted Derivatives [in Russian], p. 107.Google Scholar
  5. 5.
    H. Raudnitz and W. Bohm, J. Prakt. Chem., 123, 284 (1929).CrossRefGoogle Scholar
  6. 6.
    P. Chang, K. H. Lee, T. Shingu, T. Hirayama, I. H. Hall, and H. C. Huang, J. Nat. Prod., 45, 206 (1982).CrossRefGoogle Scholar
  7. 7.
    N. Thompson and W. Grimshaw, J. Chem. Soc., Chem. Commun., 240 (1987).Google Scholar
  8. 8.
    A. E. Shchekotikhin, E. K. Shevtsova, and V. F. Traven, Zh. Org. Khim., 43, 1687 (2007).Google Scholar
  9. 9.
    V. Ya. Fain, Electronic Absorption Spectra and Structure of Anthraquinones [in Russian], Sputnik+ (2003), Vol. 2, Disubstituted 9,10-Anthraquinones [in Russian], p. 34.Google Scholar
  10. 10.
    Yu. B. Sinkevich, A. E. Shchekotikhin, Yu. N. Luzikov, V. N. Buyanov, and L. V. Kovalenko, Khim. Geterotsikl. Soedin., 1478 (2007). [Chem. Heterocycl. Comp., 43, 1252 (2007)].Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • A. E. Shchekotikhin
    • 1
    Email author
  • Yu. N. Luzikov
    • 1
  • V. N. Buyanov
    • 2
  • M. N. Preobrazhenskaya
    • 1
  1. 1.G. F. Gauze Scientific Research Institute for Investigation of New AntibioticsMoscowRussia
  2. 2.D. I. Mendeleev Russian Chemical Technology UniversityMoscowRussia

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