Heterocyclic Analogs of 5,12-Naphthacene-Quinone. 12. Synthesis of 2-Substituted Derivatives of 4,11-Dimethoxy-5,10-Dioxo-Anthra[2,3-b]Furan-3-Carboxylic Acids
A. S. TIKHOMIROV
1, 2
,
A E Shchekotikhin
1, 2
,
Yu N Luzikov
1
,
A.M Korolev
1
,
M.N. Preobrazhenskaya
1
Publication type: Journal Article
Publication date: 2014-04-23
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
The synthesis of anthrafurandiones, by means of which it is possible to obtain a series of previously unknown 2-substituted derivatives of 4,11-dimethoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylic acids after protection of the hydroxy groups of the initial 2,3-dibromoquinizarin, was optimized. Unlike most of the analogs, 4,11-dimethoxy-5,10-dioxo-2-(trifluoromethyl)anthra[2,3-b]furan-3-carboxylic acid ester is best synthesized from 2,3-dibromoquinizarin with subsequent methylation of the hydroxy groups. The heterocyclic ring of this ester was found to have low stability during the action of alkalis. This, together with the side deacetylation of the intermediate, is probably the main reason for its low yield at the heterocyclization stage.
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TIKHOMIROV A. S. et al. Heterocyclic Analogs of 5,12-Naphthacene-Quinone. 12. Synthesis of 2-Substituted Derivatives of 4,11-Dimethoxy-5,10-Dioxo-Anthra[2,3-b]Furan-3-Carboxylic Acids // Chemistry of Heterocyclic Compounds. 2014. Vol. 50. No. 2. pp. 271-280.
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TIKHOMIROV A. S., Shchekotikhin A. E., Luzikov Yu. N., Korolev A., Preobrazhenskaya M. Heterocyclic Analogs of 5,12-Naphthacene-Quinone. 12. Synthesis of 2-Substituted Derivatives of 4,11-Dimethoxy-5,10-Dioxo-Anthra[2,3-b]Furan-3-Carboxylic Acids // Chemistry of Heterocyclic Compounds. 2014. Vol. 50. No. 2. pp. 271-280.
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TY - JOUR
DO - 10.1007/s10593-014-1471-x
UR - https://doi.org/10.1007/s10593-014-1471-x
TI - Heterocyclic Analogs of 5,12-Naphthacene-Quinone. 12. Synthesis of 2-Substituted Derivatives of 4,11-Dimethoxy-5,10-Dioxo-Anthra[2,3-b]Furan-3-Carboxylic Acids
T2 - Chemistry of Heterocyclic Compounds
AU - TIKHOMIROV, A. S.
AU - Shchekotikhin, A E
AU - Luzikov, Yu N
AU - Korolev, A.M
AU - Preobrazhenskaya, M.N.
PY - 2014
DA - 2014/04/23
PB - Springer Nature
SP - 271-280
IS - 2
VL - 50
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2014_TIKHOMIROV,
author = {A. S. TIKHOMIROV and A E Shchekotikhin and Yu N Luzikov and A.M Korolev and M.N. Preobrazhenskaya},
title = {Heterocyclic Analogs of 5,12-Naphthacene-Quinone. 12. Synthesis of 2-Substituted Derivatives of 4,11-Dimethoxy-5,10-Dioxo-Anthra[2,3-b]Furan-3-Carboxylic Acids},
journal = {Chemistry of Heterocyclic Compounds},
year = {2014},
volume = {50},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1007/s10593-014-1471-x},
number = {2},
pages = {271--280},
doi = {10.1007/s10593-014-1471-x}
}
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MLA
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TIKHOMIROV, A. S., et al. “Heterocyclic Analogs of 5,12-Naphthacene-Quinone. 12. Synthesis of 2-Substituted Derivatives of 4,11-Dimethoxy-5,10-Dioxo-Anthra[2,3-b]Furan-3-Carboxylic Acids.” Chemistry of Heterocyclic Compounds, vol. 50, no. 2, Apr. 2014, pp. 271-280. https://doi.org/10.1007/s10593-014-1471-x.
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