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. Shchekotikhin
  • 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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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • A. E. Shchekotikhin
    • 1
  • 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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