HETEROCYCLIC ANALOGS OF 5,12-NAPHTHACENE- QUINONE. 11. A NEW METHOD FOR PREPARING 4,11-DIMETHOXYANTHRA[2,3-<i>b</i>]FURAN-5,10-DIONE

Authors

  • А. С. Тихомиров Gause Institute of New Antibiotics, Russian Academy of Medical Sciences
  • А. Е. Щекотихин Gause Institute of New Antibiotics, Russian Academy of Medical Sciences
  • Ю. H. Лузиков Gause Institute of New Antibiotics, Russian Academy of Medical Sciences
  • А. М. Королев Gause Institute of New Antibiotics, Russian Academy of Medical Sciences
  • M. Н. Преображенская Gause Institute of New Antibiotics, Russian Academy of Medical Sciences

DOI:

https://doi.org/10.1007/403

Keywords:

2, 5-dihydroxy-6, 11-dioxo-6, 11-dihydroanthra[1, 2-b]furan-3-carboxylic acid derivatives, 4, 11-dimethoxyanthra[2, 3-b]furan-5, 10-dione derivatives

Abstract

A new method was developed for the synthesis of 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione and some of its previously unknown derivatives. The method was based on heterocyclization of 2-(3-haloanthraquinon-2-yl)formylacetic acid derivatives by the action of bases, leading to methyl 4,11-dimethoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylate. Subsequent acid hydrolysis of the ester group and decarboxylation of the obtained acid gave 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione. The low yield of the target compound was probably due to heterocycle instability in the 5,10-dioxo-anthra[2,3-b]furan-3-carboxylic acid derivatives in basic medium.

Authors: A. S. Tikhomirov, A. E. Shchekotikhin, Yu. N. Luzikov, A. M. Korolev, and M. N. Preobrazhenskaya

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (2), pp 241-248

http://link.springer.com/article/10.1007/s10593-013-1240-2

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Published

2013-03-18

Issue

No. 2 (2013)

Section

Original Papers