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-halo-anthraquinon-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.
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Notes
Here and subsequently all the signals in the 13C NMR spectra without designations belong to the quaternary carbon atoms.
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*For Communication 10, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 264-272, February, 2013.
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Tikhomirov, A.S., Shchekotikhin, A.E., Luzikov, Y.N. et al. Heterocyclic analogs of 5,12-naphthacene-quinone. 11*. A new method for preparing 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione. Chem Heterocycl Comp 49, 241–248 (2013). https://doi.org/10.1007/s10593-013-1240-2
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DOI: https://doi.org/10.1007/s10593-013-1240-2