HETEROCYCLIC ANALOGS OF 5,12-NAPHTHACENEQUINONE. 7. SYNTHESIS OF NAPHTHO[2,3-<i>f</i>]ISATIN-5,10-DIONE DERIVATIVES

Authors

  • А. Е. Щекотихин G. F. Gauze Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow 119021
  • Ю. H. Лузиков G. F. Gauze Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow 119021
  • Ю. Б. Синкевич Russian D. I. Mendeleev University of Chemical Technology, Moscow 125047
  • В. Н. Буянов Russian D. I. Mendeleev University of Chemical Technology, Moscow 125047
  • M. Н. Преображенская G. F. Gauze Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow 119021

DOI:

https://doi.org/10.1007/7215

Keywords:

4, 11-dihydroxynaphtho[2, 3-f]indole-2, 3, 5, 10-tetraone, 11-dimethoxynaphtho[2, 3-f]indole-5, 10-dione, hydrolysis, demethylation, chlorination

Abstract

On chlorination of 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione with sulfuryl chloride in chloroform, its mono-, di-, and trichloro derivatives are formed depending on the conditions. Hydrolysis of the di- and trichloro derivatives gives a new polycondensed derivative of isatin, 4,11-dimethoxynaphtho-[2,3-f]isatin-5,10-dione. Its demethylation occurs effectively on extended heating with HBr in acetic acid and leads to 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-dione (4,11-di-hydroxynaphtho[2,3-f]indole-2,3,5,10-tetraone).

How to Cite
Shchekotikhin, A. E.; Luzikov, Y. N.; Sinkevich, Y. B.; Buyanov, V. N.; Preobrazhenskaya, M. N.  Chem. Heterocycl. Compd. 2008, 44, 1245. [Khim. Geterotsikl. Soedin. 2008, 1532.]

For this article in the English edition see DOI 10.1007/s10593-009-0173-2


Downloads

Published

2022-11-25

Issue

No. 10 (2008)

Section

Original Papers