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Thiophene

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Gennady L. Rusinov - One of the best experts on this subject based on the ideXlab platform.

  • Construction of 2,3-disubstituted benzo[b]thieno[2,3-d]Thiophenes and benzo[4,5]selenopheno[3,2-b]Thiophenes using the Fiesselmann Thiophene synthesis.
    Organic & Biomolecular Chemistry, 2020
    Co-Authors: Roman A. Irgashev, Nadezhda S. Demina, Gennady L. Rusinov
    Abstract:

    A series of 3-(hetero)aryl-substituted benzo[b]thieno[2,3-d]Thiophenes, bearing various electron withdrawing groups at C-2 position of their scaffolds, were obtained using a convenient approach based on the Fiesselmann Thiophene synthesis. To realize this strategy, the Friedel–Crafts acylation of (hetero)arenes with easily accessible 3-chlorobenzo[b]Thiophene-2-carbonyl chlorides was initially performed to afford 3-chloro-2-(hetero)aroylbenzo[b]Thiophenes. The latter ketones were treated either with methyl thioglycolate in the presence of DBU and calcium oxide powder or successively with sodium sulfide, an alkylating agent, containing methylene active component, and also DBU and calcium oxide, to form the desired benzo[b]thieno[2,3-d]Thiophene derivatives. In addition, similar benzo[4,5]selenopheno[3,2-b]Thiophene derivatives were prepared in the same manner using 3-bromobenzo[b]selenophen-2-yl substrates. The obtained functional derivatives of both benzo[b]thieno[2,3-d]Thiophene and benzo[4,5]selenopheno[3,2-b]Thiophene are of interest for further elaboration of organic semiconductor materials.

  • Synthesis of aryl-substituted thieno[3,2-b]Thiophene derivatives and their use for N,S-heterotetracene construction.
    Beilstein journal of organic chemistry, 2019
    Co-Authors: Nadezhda S. Demina, Roman A. Irgashev, Nikita A. Kazin, Nikolay A. Rasputin, Gennady L. Rusinov
    Abstract:

    Fiesselmann Thiophene synthesis was applied for the convenient construction of thieno[3,2-b]Thiophene derivatives. Thus, new 5- or 6-aryl-3-hydroxythieno[3,2-b]Thiophene-2-carboxylates were obtained by condensation of 5- or 4-aryl-3-chloroThiophene-2-carboxylates, respectively, with methyl thioglycolate in the presence of potassium tert-butoxide. The saponification of the resulting esters, with decarboxylation of the intermediating acids, gave the corresponding thieno[3,2-b]thiophen-3(2H)-ones. The latter ketones were used to synthesize new N,S-heterotetracenes, namely 9H-thieno[2',3':4,5]thieno[3,2-b]indoles by their treatment with arylhydrazines in accordance with the Fischer indolization reaction.

Henry N. C. Wong - One of the best experts on this subject based on the ideXlab platform.

  • Synthetic Applications of 3,4-Bis(trimethylsilyl)Thiophene: Unsymmetrically 3,4-Disubstituted Thiophenes and 3,4-DidehydroThiophene(,).
    The Journal of Organic Chemistry, 1997
    Co-Authors: Henry N. C. Wong
    Abstract:

    3,4-Bis(trimethylsilyl)Thiophene (1a) was synthesized by three routes:  (a) 1,3-dipolar cycloaddition; (b) modification of 3,4-dibromoThiophene; and (c) intermolecular thiazole−alkyne Diels−Alder reaction. 3,4-Bis(trimethylsilyl)Thiophene (1a) can function as a versatile building block for the construction of unsymmetrically 3,4-disubstituted Thiophenes utilizing its stepwise regiospecific mono-ipso-substitution followed by palladium-catalyzed cross-coupling reactions. In this manner, Thiophenes 15, 16, 17a−j, 19a,b, 20, 22a−c, 23a,b, 24a−d, 25a−c, and 27a−j were prepared. The Thiophene-3,4-diyl dimer 28 and Thiophene-3,4-diyl tetramer 29 were also realized by palladium-catalyzed self-coupling reaction of organoboroxines. The stannylThiophene 31, formed by conversion of the C−Si bond to a C−Sn bond via boroxine 26c underwent both carbonylative coupling and lithiation followed by quenching with electrophiles to afford unsymmetrically 3,4-disubstituted Thiophenes 33 and 36a−c as well. Moreover, 3,4-bis(trim...

  • Regiospecific synthesis of 3,4-disubstituted Thiophenes
    Chemical Communications, 1996
    Co-Authors: Henry N. C. Wong
    Abstract:

    3,4-Bis(trimethylsilyl)Thiophene and several other 3,4-disubstituted Thiophenes are synthesised by an unprecedented intermolecular cycloaddition–cycloreversion procedure between disubstituted acetylenes and 4-methyl- or 4-phenyl-thiazole; 3,4-bis(trimethylsilyl)Thiophene undergoes consecutive regiospecific mono-ipso-iodination and palladium-catalysed reactions to provide unsymmetrically 3,4-disubstituted Thiophenes.

Roman A. Irgashev - One of the best experts on this subject based on the ideXlab platform.

  • Construction of 2,3-disubstituted benzo[b]thieno[2,3-d]Thiophenes and benzo[4,5]selenopheno[3,2-b]Thiophenes using the Fiesselmann Thiophene synthesis.
    Organic & Biomolecular Chemistry, 2020
    Co-Authors: Roman A. Irgashev, Nadezhda S. Demina, Gennady L. Rusinov
    Abstract:

    A series of 3-(hetero)aryl-substituted benzo[b]thieno[2,3-d]Thiophenes, bearing various electron withdrawing groups at C-2 position of their scaffolds, were obtained using a convenient approach based on the Fiesselmann Thiophene synthesis. To realize this strategy, the Friedel–Crafts acylation of (hetero)arenes with easily accessible 3-chlorobenzo[b]Thiophene-2-carbonyl chlorides was initially performed to afford 3-chloro-2-(hetero)aroylbenzo[b]Thiophenes. The latter ketones were treated either with methyl thioglycolate in the presence of DBU and calcium oxide powder or successively with sodium sulfide, an alkylating agent, containing methylene active component, and also DBU and calcium oxide, to form the desired benzo[b]thieno[2,3-d]Thiophene derivatives. In addition, similar benzo[4,5]selenopheno[3,2-b]Thiophene derivatives were prepared in the same manner using 3-bromobenzo[b]selenophen-2-yl substrates. The obtained functional derivatives of both benzo[b]thieno[2,3-d]Thiophene and benzo[4,5]selenopheno[3,2-b]Thiophene are of interest for further elaboration of organic semiconductor materials.

  • Synthesis of aryl-substituted thieno[3,2-b]Thiophene derivatives and their use for N,S-heterotetracene construction.
    Beilstein journal of organic chemistry, 2019
    Co-Authors: Nadezhda S. Demina, Roman A. Irgashev, Nikita A. Kazin, Nikolay A. Rasputin, Gennady L. Rusinov
    Abstract:

    Fiesselmann Thiophene synthesis was applied for the convenient construction of thieno[3,2-b]Thiophene derivatives. Thus, new 5- or 6-aryl-3-hydroxythieno[3,2-b]Thiophene-2-carboxylates were obtained by condensation of 5- or 4-aryl-3-chloroThiophene-2-carboxylates, respectively, with methyl thioglycolate in the presence of potassium tert-butoxide. The saponification of the resulting esters, with decarboxylation of the intermediating acids, gave the corresponding thieno[3,2-b]thiophen-3(2H)-ones. The latter ketones were used to synthesize new N,S-heterotetracenes, namely 9H-thieno[2',3':4,5]thieno[3,2-b]indoles by their treatment with arylhydrazines in accordance with the Fischer indolization reaction.

Nadezhda S. Demina - One of the best experts on this subject based on the ideXlab platform.

  • Construction of 2,3-disubstituted benzo[b]thieno[2,3-d]Thiophenes and benzo[4,5]selenopheno[3,2-b]Thiophenes using the Fiesselmann Thiophene synthesis.
    Organic & Biomolecular Chemistry, 2020
    Co-Authors: Roman A. Irgashev, Nadezhda S. Demina, Gennady L. Rusinov
    Abstract:

    A series of 3-(hetero)aryl-substituted benzo[b]thieno[2,3-d]Thiophenes, bearing various electron withdrawing groups at C-2 position of their scaffolds, were obtained using a convenient approach based on the Fiesselmann Thiophene synthesis. To realize this strategy, the Friedel–Crafts acylation of (hetero)arenes with easily accessible 3-chlorobenzo[b]Thiophene-2-carbonyl chlorides was initially performed to afford 3-chloro-2-(hetero)aroylbenzo[b]Thiophenes. The latter ketones were treated either with methyl thioglycolate in the presence of DBU and calcium oxide powder or successively with sodium sulfide, an alkylating agent, containing methylene active component, and also DBU and calcium oxide, to form the desired benzo[b]thieno[2,3-d]Thiophene derivatives. In addition, similar benzo[4,5]selenopheno[3,2-b]Thiophene derivatives were prepared in the same manner using 3-bromobenzo[b]selenophen-2-yl substrates. The obtained functional derivatives of both benzo[b]thieno[2,3-d]Thiophene and benzo[4,5]selenopheno[3,2-b]Thiophene are of interest for further elaboration of organic semiconductor materials.

  • Synthesis of aryl-substituted thieno[3,2-b]Thiophene derivatives and their use for N,S-heterotetracene construction.
    Beilstein journal of organic chemistry, 2019
    Co-Authors: Nadezhda S. Demina, Roman A. Irgashev, Nikita A. Kazin, Nikolay A. Rasputin, Gennady L. Rusinov
    Abstract:

    Fiesselmann Thiophene synthesis was applied for the convenient construction of thieno[3,2-b]Thiophene derivatives. Thus, new 5- or 6-aryl-3-hydroxythieno[3,2-b]Thiophene-2-carboxylates were obtained by condensation of 5- or 4-aryl-3-chloroThiophene-2-carboxylates, respectively, with methyl thioglycolate in the presence of potassium tert-butoxide. The saponification of the resulting esters, with decarboxylation of the intermediating acids, gave the corresponding thieno[3,2-b]thiophen-3(2H)-ones. The latter ketones were used to synthesize new N,S-heterotetracenes, namely 9H-thieno[2',3':4,5]thieno[3,2-b]indoles by their treatment with arylhydrazines in accordance with the Fischer indolization reaction.

George J. Wullems - One of the best experts on this subject based on the ideXlab platform.

  • Thiophene bioconversions in Tagetes protoplasts
    Plant Science, 1995
    Co-Authors: John J.m.r. Jacobs, Marc Stalman, Anton F. Croes, George J. Wullems
    Abstract:

    Abstract The Thiophene content of Tagetes protoplasts isolated from various organs, and the ability of these protoplasts to convert or synthesize Thiophenes were investigated and compared with the Thiophene content and metabolic capacities of intact organs. A substantial fraction of Thiophenes is localized intracellularly in hypocotyls, whereas another significant fraction is localized in the extracellular spaces. Protoplasts originating both from hypocotyls and leaf blades can perform the reactions required for formation of the second Thiophene ring and for hydroxylation and acetylation of Thiophenes, although the organs from which these protoplasts are isolated differ greatly in Thiophene content and Thiophene synthesizing capacity. All reactions of Thiophene synthesis from formation of the first ring onwards can be carried out by hypocotyl protoplasts.

  • effect of exogenous auxin on root morphology and secondary metabolism in tagetes patula hairy root cultures
    Physiologia Plantarum, 1995
    Co-Authors: R R J Arroo, Anton F. Croes, A Develi, H Meijers, E Van De Westerlo, A Kemp, George J. Wullems
    Abstract:

    In this paper the effects of indole-3-acetic acid (IAA) on growth of Tagetes patula hairy root cultures and secondary product formation are presented. The biosynthesis of Thiophenes, sulfurous compounds with nematicidal activity, was inhibited by IAA application, as was evident from a decrease of [ 35 S]sulfur incorporation. The inhibition only occurred after the roots had developed numerous laterals as a result of auxin action. However, in roots cultured in the absence of IAA, there was no significant correlation between branching and Thiophene accumulation. Therefore, development of lateral roots is not a sufficient condition for a low capacity to synthesize Thiophenes. The highest rate of Thiophene accumulation in the roots is found during the late exponential growth phase, when the weight increase of a root culture is at its maximum. Hence, growth and the production of Thiophenes appear to be compatible in T. patula hairy roots