HETEROCYCLIC ANALOGS OF 5,12-NAPHTHACENEQUINONE. 6. SYNTHESIS OF 4,11-DIMETHOXY DERIVATIVES OF ANTHRA[2,3-<i>b</i>]THIOPHENE-5,10-DIONE AND ANTHRA[2,3-<i>d</i>]ISOTHIAZOLE-5,10-DIONE

Authors

  • А. Е. Щекотихин G. F. Gause Institute of New Antibiotics, Moscow 119021
  • Ю. H. Лузиков G. F. Gause Institute of New Antibiotics, Moscow 119021
  • В. Н. Буянов D. Mendeleev University of Chemical Technology, Moscow 125190
  • M. Н. Преображенская G. F. Gause Institute of New Antibiotics, Moscow 119021

DOI:

https://doi.org/10.1007/7548

Keywords:

3-chloro-1, 4-dimethoxyanthracene-9, 10-dione-2-carbaldehyde, 4, 11-dimethoxyanthra[2, 3-d]isothiazole-5, 10-dione, 3-b]thiophene-5, 10-dione derivatives, fluorescence spectra, Stokes shift

Abstract

Condensation of 2-formyl- or 2-cyano-3-chloro-1,4-dimethoxyanthraquinone with methyl thioglycolate in the presence of base gave methyl 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione-2-carboxylate and its 3-amino derivative respectively. Hydrolysis of the ester group in methyl 4,11-dimethoxy-anthra[2,3-b]thiophene-5,10-dione-2-carboxylate and subsequent decarboxylation of the carboxylic acid formed gave 4,11-dimethoxyanthra[2,3-b]thiophene-5,10-dione. Condensation of 3-chloro-2-formyl-1,4-dimethoxyanthraquinone with ammonia in the presence of sulfur gave 4,11-dimethoxy-anthra[2,3-d]isothiazole-5,10-dione.

How to Cite
Shchekotikhin, A. E.; Lusikov, Yu. N.; Buyanov, V. N.; Preobrazhenskaya, M. N.  Chem. Heterocycl. Compd. 2007, 43, 439. [Khim. Geterotsikl. Soedin. 2007, 538.]

For this article in the English edition see DOI 10.1007/s10593-007-0063-4


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Published

2023-03-23

Issue

No. 4 (2007)

Section

Original Papers