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

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

Nadezhda S Demina, Nikita A Kazin, Nikolay A Rasputin, Roman A Irgashev, Gennady L Rusinov

Beilstein J Org Chem. 2019 Nov 12;15:2678-2683.

PMID: 31807203

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP148961880	2-Tributylstannylbenzo[b]thiophene		148961-88-0	Price
AP420089516	Thiophene-2		420089-51-6	Price

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