Chemistry of Heterocyclic Compounds

, Volume 42, Issue 6, pp 746–752 | Cite as

Heterocyclic analogs of 5,12-naphthacene-quinone. 3. Synthesis of 4,11-diaminonaphtho-[2,3-f]indole-5,10-dione and certain of its derivatives

  • A. E. Shchekotikhin
  • Yu. N. Luzikov
  • V. N. Buyanov
  • M. N. Preobrazhenskaya
Article

Abstract

Nucleophilic substitution of methoxy groups in 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione by the action of primary and secondary alkylamines, or arylamines leads to the formation of N-alkyl or N-aryl derivatives of 4,11-diaminonaphtho[2,3-f]indole-5,10-dione respectively. 4,11-Diamino-1H-naphtho-[2,3-f]indole-5,10-dione is obtained by the dealkylation of 4,11-bis[(1-phenylethyl)amino]-1Hnaphtho[ 2,3-f]indole-5,10-dione in the presence of a Lewis acid (BBr3).

Keywords

4,11-diamino-1H-naphtho[2,3-f]indole-5,10-dione 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione dealkylation of alkylamino groups nucleophilic aromatic substitution solvatochromism 

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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • A. E. Shchekotikhin
    • 1
  • Yu. N. Luzikov
    • 1
  • V. N. Buyanov
    • 2
  • M. N. Preobrazhenskaya
    • 1
  1. 1.G. F. Gauze Institute of New Antibioticsthe Russian Academy of Medical Science MoscowRussia
  2. 2.Russian D. I. Mendeleev University of Chemical TechnologyMoscow

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