Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction

Beilstein Journal of Organic Chemistry

卷:15

Nikita A. Kazin¹  Roman A. Irgashev¹  Gennady L. Rusinov¹  Nadezhda S. Demina¹  Nikolay A. Rasputin¹ 

[1] Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskoy St., 22, Ekaterinburg, 620990, Russia;

关键词: fiesselmann thiophene synthesis;    fischer indole synthesis;    n,s-heteroacene;    thieno[3,2-b]thiophene;    thieno[2',3':4,5]thieno[3,2-b]indole;   

DOI  :  10.3762/bjoc.15.261

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown