HETEROCYCLIC ANALOGS OF 5,12-NAPHTHACENEQUINONE. 8. SYNTHESIS OF FURANOANTHRAQUINONES

Authors

  • А. Е. Щекотихин G. F. Gauze Scientific Research Institute for Investigation of New Antibiotics, Moscow 119021
  • Ю. H. Лузиков G. F. Gauze Scientific Research Institute for Investigation of New Antibiotics, Moscow 119021
  • В. Н. Буянов D. I. Mendeleev Russian Chemical Technology University, Moscow 125047
  • M. Н. Преображенская G. F. Gauze Scientific Research Institute for Investigation of New Antibiotics, Moscow 119021

DOI:

https://doi.org/10.1007/6815

Keywords:

anthra[2, 1-d][1, 3]dioxole-6, 11-dione, 3-b]furan-5, 10-dione, anthra[1, 2-b]furan-6, 3-b]furan-2, 6, 11(3H)-trione, 2, 3-dichloroquinizarine, methyl pivaloylacetate, condensation, modification

Abstract

During the condensation of 2,3-dichloroquinizarine  with methyl pivaloylacetate in the presence of potassium carbonate in dimethyl sulfoxide the  main reaction products are derivatives of angular 3-pivaloylanthra[1,2-b]furan-2,6,11(3H)-trione (about 70%) and anthra[2,1-d][1,3]dioxole-6,11-dione (15%), whereas the yield of the targeted linear methyl 2-tert-butyl-4,11-dihydroxyanthra[2,3-b]furan-5,10-dione-3-carboxylate is only 2%. Methods are developed for modification of the obtained 3-pivaloylanthra[1,2-b]furan-2,6,11(3H)-trione, making it possible to use it for the synthesis of the tert-butyl derivatives of linear anthra[2,3-b]furan-5,10-dione or angular anthra[1,2-b]furan-6,11-dione.

How to Cite
Shchekotikhin, A. E.; Luzikov, Yu. N.; Buyanov, V. N.; Preobrazhenskaya, M. N.  Chem. Heterocycl. Compd. 2009, 45, 151. [Khim. Geterotsikl. Soedin. 2009, 191.]

For this article in the English edition see DOI 10.1007/s10593-009-0244-4


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Published

2022-05-23

Issue

No. 2 (2009)

Section

Original Papers