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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 2, pp 194–203 | Cite as

Heterocyclic analogs of 5,12-naphthacenequinone 9*. Study of the synthesis and reactivity of 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones

  • A. N. Nikitina
  • A. E. ShchekotikhinEmail author
  • Y. N. Luzikov
  • A. M. Korolev
  • V. N. Buyanov
  • M. N. Preobrazhenskaya
Article

A preparative method has been developed for N-alkyl 4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones. Condensation reactions with several N- and C-nucleophiles have been carried out to give the corresponding derivatives at position 3. An efficient method has been discovered for the demethylation of the N-alkyl-4,11-dimethoxynaphtho[2,3-f]isatin-5,10-diones to give a high yield of N-substituted 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-diones. Successive halogenation using phosphorus penta-chloride and acylation of tert-butylamine by the intermediate 2-chloro derivative converted 4,11-di-methoxynaphtho[2,3-f]isatin-5,10-dione to the 2-amino-3H-naphtho[2,3-f]indole-3,5,10-trione derivative.

Keywords

4,11-dimethoxynaphtho[2,3-f]isatin-5,10-dione 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione alkylation halogenation demethylation condensation derivatives 

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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • A. N. Nikitina
    • 1
  • A. E. Shchekotikhin
    • 1
    Email author
  • Y. N. Luzikov
    • 1
  • A. M. Korolev
    • 1
  • V. N. Buyanov
    • 2
  • M. N. Preobrazhenskaya
    • 1
  1. 1.G. F. Gause Institute of New AntibioticsRussian Academy of Medical SciencesMoscowRussia
  2. 2.D. I. Mendeleev University of Chemical Technology of RussiaMoscowRussia

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