HETEROCYCLIC ANALOGS OF 5,12-NAPHTHACENEQUINONE. 9. STUDY OF THE SYNTHESIS AND REACTIVITY OF 4,11-DIMETHOXYNAPHTHO[2,3-<i>f</i>]ISATIN-5,10-DIONES

Authors

  • А. Н. Никитина G. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences
  • А. Е. Щекотихин G. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences
  • Ю. H. Лузиков G. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences
  • А. М. Королев G. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences
  • В. Н. Буянов D. I. Mendeleev University of Chemical Technology of Russia
  • M. Н. Преображенская G. F. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences

DOI:

https://doi.org/10.1007/2134

Keywords:

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

Abstract

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.

How to Cite
Nikitina, A. N.; Shchekotikhin, A. E.; Luzikov, Y. N.; Korolev, A. M.; Buyanov, V. N.; Preobrazhenskaya, M. N. Chem. Heterocycl. Compd. 2011, 47(2), 194. [Khim. Geterotsikl. Soedin. 2011, 245.]

For this article in the English edition see DOI 10.1007/s10593-011-0740-1

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Published

2014-12-04

Issue

No. 2 (2011)

Section

Original Papers