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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

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Chemistry of Heterocyclic Compounds Aims and scope

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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Notes

  1. The ratio of Z,E-isomers was established from the integral ratio of the aldehyde proton signals in 1Н NMR spectra.22

  2. The amounts of Z,E-isomers were established from the integral ratio of aldehyde proton signals in 1Н NMR spectra.22

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This work was performed with financial support from the Ministry of Education and Science of the Russian Federation (project No. 4.1657.2017/4.6).

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Authors and Affiliations

  1. Omsk State Technical University, 11 Mira Ave., Omsk, 644050, Russia

    Anastasia S. Kostyuchenko, Evgeny B. Ulyankin, Anton L. Shatsauskas, Vladislav Yu. Shuvalov & Alexander S. Fisyuk

  2. F. M. Dostoyevsky Omsk State University, 55a Mira Ave., Omsk, 644077, Russia

    Anastasia S. Kostyuchenko, Evgeny B. Ulyankin, Anton L. Shatsauskas, Vladislav Yu. Shuvalov & Alexander S. Fisyuk

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  1. Anastasia S. Kostyuchenko
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  2. Evgeny B. Ulyankin
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  4. Vladislav Yu. Shuvalov
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  5. Alexander S. Fisyuk
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Correspondence to Alexander S. Fisyuk.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(11), 1026–1032

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Kostyuchenko, A.S., Ulyankin, E.B., Shatsauskas, A.L. 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. Chem Heterocycl Comp 54, 1026–1032 (2018). https://doi.org/10.1007/s10593-018-2386-8

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  • DOI: https://doi.org/10.1007/s10593-018-2386-8

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