New approach to the synthesis of 2,2':5',2''-terthiophene-5,5''-and 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids
Anastasia S. Kostyuchenko
1, 2
,
Evgeny B. Ulyankin
1, 2
,
Anton L. Shatsauskas
1, 2
,
Vladislav Yu. Shuvalov
1, 2
,
Alexander S. Fisyuk
1, 2
Publication type: Journal Article
Publication date: 2018-11-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
The reaction of bromosuccinimide with esters of 3-substituted 2,2'-bithiophene-5-carboxylic acids was used to obtain their 5'-bromo derivatives, which were further converted to esters of 3,3'''-disubstituted 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids by heating in DMF with catalytic amounts of Pd(PPh3)4. Ester of 3-decyl-2,2'-bithiophene-5-carboxylic acid was acylated at the С-5' position with lauroyl chloride in the presence of SnCl4, producing the respective ketone that was used in Vilsmeier–Haack reaction (DMF, POCl3). The 3-chloroacrylaldehyde derivative that was thus obtained was further used in reaction with ethyl thioglycolate in the presence of sodium ethoxide, giving ester of 3,3''-decyl-2,2':5',2''-terthiophene-5,5''-dicarboxylic acid. Alkaline hydrolysis of the obtained esters led to the corresponding 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''- and 2,2':5',2''-terthiophene-5,5''-dicarboxylic acids.
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Kostyuchenko A. S. et al. New approach to the synthesis of 2,2':5',2''-terthiophene-5,5''-and 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids // Chemistry of Heterocyclic Compounds. 2018. Vol. 54. No. 11. pp. 1026-1032.
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Kostyuchenko A. S., Ulyankin E. B., Shatsauskas A. L., Shuvalov V. Y., Fisyuk A. S. New approach to the synthesis of 2,2':5',2''-terthiophene-5,5''-and 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids // Chemistry of Heterocyclic Compounds. 2018. Vol. 54. No. 11. pp. 1026-1032.
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TY - JOUR
DO - 10.1007/s10593-018-2386-8
UR - https://doi.org/10.1007/s10593-018-2386-8
TI - New approach to the synthesis of 2,2':5',2''-terthiophene-5,5''-and 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids
T2 - Chemistry of Heterocyclic Compounds
AU - Kostyuchenko, Anastasia S.
AU - Ulyankin, Evgeny B.
AU - Shatsauskas, Anton L.
AU - Shuvalov, Vladislav Yu.
AU - Fisyuk, Alexander S.
PY - 2018
DA - 2018/11/01
PB - Springer Nature
SP - 1026-1032
IS - 11
VL - 54
SN - 0009-3122
SN - 1573-8353
ER -
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BibTex (up to 50 authors)
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@article{2018_Kostyuchenko,
author = {Anastasia S. Kostyuchenko and Evgeny B. Ulyankin and Anton L. Shatsauskas and Vladislav Yu. Shuvalov and Alexander S. Fisyuk},
title = {New approach to the synthesis of 2,2':5',2''-terthiophene-5,5''-and 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids},
journal = {Chemistry of Heterocyclic Compounds},
year = {2018},
volume = {54},
publisher = {Springer Nature},
month = {nov},
url = {https://doi.org/10.1007/s10593-018-2386-8},
number = {11},
pages = {1026--1032},
doi = {10.1007/s10593-018-2386-8}
}
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MLA
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Kostyuchenko, Anastasia S., et al. “New approach to the synthesis of 2,2':5',2''-terthiophene-5,5''-and 2,2':5',2'':5'',2'''-quaterthiophene-5,5'''-dicarboxylic acids.” Chemistry of Heterocyclic Compounds, vol. 54, no. 11, Nov. 2018, pp. 1026-1032. https://doi.org/10.1007/s10593-018-2386-8.