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Synthesis of alkyl-substituted ethyl 2,2':5',2'':5'',2'''-quaterthiophene-5-and 5-(biphenyl-4-yl)thiophene-2-carboxylates

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Chemistry of Heterocyclic Compounds Aims and scope

Acylation of 2,2':5',2''-terthiophene and biphenyl gave 1-(2,2':5',2''-terthiophen-5-yl)dodecan-1-one and 1-(biphenyl-4-yl)dodecan-1-one, which upon treatment with phosphorus oxychloride and dimethylformamide were converted to 2-[(2,2':5',2''-terthiophen-5-yl)-chloromethylidene]dodecanal and 2-[(biphenyl-4-yl)chloromethylidene]dodecanal. The reaction of these compounds with ethyl 2-mercaptoacetate led to the formation of ethyl 3-decyl-2,2':5',2'':5'',2'''-quaterthiophene-5- and 5-(biphenyl-4-yl)-4-decylthiophene-2-carboxylates, which are of interest as building blocks for the synthesis of organic semiconductors. Ethyl 3-decyl-2,2':5',2'':5'',2'''-quaterthiophene-5-carboxylate was also obtained by palladium-catalyzed cross coupling of ethyl 5'-bromo-3-decyl-2,2'-bithiophene-5-carboxylate with 2,2'-bithiophene.

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This work was performed with financial support from the Russian Foundation for Basic Research (project 15-43-04313-Sibir'-a, 16-33-00340 mol_a) and project ''5-100'' of the People's Friendship University of Russia.

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Authors and Affiliations

  1. Omsk State Technical University, Laboratory of New Organic Materials, 11 Mir Ave., Omsk, 644050, Russia

    Anastasia S. Kostyuchenko & Alexander S. Fisyuk

  2. Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Anastasia S. Kostyuchenko

  3. F. M. Dostoyevskii Omsk State University, 55a Mir Ave., Omsk, 644077, Russia

    Ekaterina A. Drozdova & Alexander S. Fisyuk

Authors
  1. Anastasia S. Kostyuchenko
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  2. Ekaterina A. Drozdova
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  3. Alexander S. Fisyuk
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Correspondence to Alexander S. Fisyuk.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(1), 92–96

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Kostyuchenko, A.S., Drozdova, E.A. & Fisyuk, A.S. Synthesis of alkyl-substituted ethyl 2,2':5',2'':5'',2'''-quaterthiophene-5-and 5-(biphenyl-4-yl)thiophene-2-carboxylates. Chem Heterocycl Comp 53, 92–96 (2017). https://doi.org/10.1007/s10593-017-2026-8

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  • DOI: https://doi.org/10.1007/s10593-017-2026-8

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