HETEROCYCLIC ANALOGS OF 5,12-NAPHTHACENEQUINONE. 3. SYNTHESIS OF 4,11-DIAMINONAPHTHO[2,3-<i>f</i>]INDOLE-5,10-DIONE AND CERTAIN OF ITS DERIVATIVES

Authors

  • А. Е. Щекотихин G. F. Gauze Institute of New Antibiotics, the Russian Academy of Medical Science Moscow 119021
  • Ю. H. Лузиков G. F. Gauze Institute of New Antibiotics, the Russian Academy of Medical Science Moscow 119021
  • В. Н. Буянов Russian D. I. Mendeleev University of Chemical Technology, Moscow 125190
  • M. Н. Преображенская G. F. Gauze Institute of New Antibiotics, the Russian Academy of Medical Science Moscow 119021

DOI:

https://doi.org/10.1007/7950

Keywords:

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

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]-1H-naphtho[2,3-f]indole-5,10-dione in the presence of a Lewis acid (BBr3).

How to Cite
Shchekotikhin, A. E.; Luzikov, Yu. N.; Buyanov, V. N.; Preobrazhenskaya, M. N.  Chem. Heterocycl. Compd. 2006, 42, 746. [Khim. Geterotsikl. Soedin. 2006, 854.]

For this article in the English edition see DOI 10.1007/s10593-006-0156-5


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Published

2023-08-14

Issue

No. 6 (2006)

Section

Original Papers