Efficient one pot preparation of variously substituted thieno [2,3- b ] thiophene (original) (raw)
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Facile and Convenient Synthesis of New Thieno[2,3-b]-Thiophene Derivatives
Molecules, 2010
A facile and convenient synthesis of bis(2-(1H-benzo[d]imidazol-2(3H)ylidene)-3-oxopropanenitrile), bis((3-amino-5-(methylthio)-1H-pyrazol-4-yl)methanone) and bis(2-thioxo-1,2-dihydropyrimidine-5-carbonitrile) derivatives incorporating a thieno-[2,3-b]thiophene moiety via versatile, readily accessible diethyl 3,4-dimethylthieno-[2,3b]thiophene-2,5-dicarboxylate (1) is described.
Journal of Molecular Structure, 2012
1,1 0-(3-Methyl-4-phenylthieno[2,3-b]thiophene-2,5-diyl)bis(4,4,4 triethoxybut-2-en-1-one)-3 has been reported by one-pot reaction of enaminone derivative 2 with triethylorthoformate in fairly high yields. The hitherto unknown bis-hydroxyl amine derivatives 4 via N-nucleophile under basic conditions is described. Additionally, the novel Compound 5 were synthesized by the cyclization of enaminone derivative 2 using AcOH with the aid of catalytic amount of AcONH 4. Nevertheless, facile reaction sequences for the preparation of 6, 7, 8a-c, and 9a-c starting with 1,1 0-(3-methyl-4-phenylthieno[2,3-b]thiophene-2,5diyl)diethanone 1 have been developed. Finally, several bis-heterocycles 10a-f were synthesized through a stepwise formation of hydrazone followed by a Michael 1,4-addition of the nucleophile nitrogen atom and provides a convenient access to an important class of nitrogen heterocycles.
Reactions of Some New Thienothiophene Derivatives
Molecules, 2011
Facile and convenient syntheses of bisdimethylthieno[2,3-b]thiophen-2,5-diyl bis(oxazole-2-amine), bis(1H-imidazol-2-amine), bis((3a)-H-indole),[1,2-a]pyrimidine), bis(1H-imidazo[1,2-b][1,2,4]triazole) and bis(9H-benzo[d]imidazo[1,2-a]imidazole) derivatives incorporating a thieno[2,3-b]thiophene moiety from the versatile and readily accessible 1,1'(3,4-dimethylthieno[2,3-b]thiophene-2,5-diyl)-bis(2-bromo-ethanone) (1) are described.
Beilstein Journal of Organic Chemistry, 2019
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.
Synthesis and Characterization of New Thieno[3,2-b]thiophene Derivatives
Three derivatives of thieno[3,2-b]thiophene end-capped with phenyl units have been synthesized and characterized by MALDI TOF mass spectroscopy, elemental analysis, UV-vis absorption spectroscopy and thermogravimetric analysis (TGA). All compounds were prepared using Pd-catalyzed Stille or Suzuki coupling reactions. Optical measurements and thermal analysis revealed that these compounds are promising candidates for p-type organic semiconductor applications.
Acta chimica Slovenica, 2011
Ethyl 3,4-diamino-5-cyanothieno[2,3-b]thiophene-2-carboxylate (1) was treated with a mixture of carbon disulfide and halo compounds to give the corresponding bisthiazole and bisthiolane derivatives 2-4. Treatment of compound 1 with 2,5-dimethoxytetrahydrofuran gave the corresponding 3,4-dipyrrol-1-ylthienothiophene (5). Condensation of compound 5 with hydrazine afforded the carbohydrazide derivative 6, which was treated with CS2 or PhNCS to afford oxadiazole or triazole derivatives 7a,b. The cycloaddition reaction of compound 5 with CS2 or PhNCS under phase transfer conditions gave 1,4-thiazepino- or 1,4-diazepinothieno[2,3-b]thiophenes 8 and 9, respectively. Basic hydrolysis of compound 1 yielded 3,4-diaminothieno[2,3-b]thiophene (10), which was subjected to react with different reagents to give the corresponding bispyrido- and bispyrrolothieno[2,3-b]thiophenes, and bisarylideneaminothieno[2,3-b]thiophenes 11-15, respectively.