14006-55-4Relevant articles and documents
An Effective Route to Dithieno[3,2- b:2′,3′- d ]thiophene-Based Hexaheteroacenes
Demina, Nadezhda S.,Bayankina, Polina E.,Irgashev, Roman A.,Kazin, Nikita A.,Rusinov, Gennady L.
, p. 1009 - 1013 (2021)
A series of 12 H -[1]benzo[4′′,5′′]thieno[2′′,3′′:4′,5′]thieno[2′,3′:4,5]thieno[3,2- b ]indoles were efficiently prepared in three steps starting from available benzo[ b ]thieno[2,3- d ]thiophen-3(2 H)-ones. These fused ketones were treated with the Vilsmeier reagent and hydroxylamine hydrochloride to give the corresponding 3-chlorobenzo[ b ]thieno[2,3- d ]thiophene-2-carbonitriles, which then reacted with methyl sulfanylacetate to form methyl 3-aminobenzo[4′,5′]thieno[2′,3′:4,5]thieno[3,2- b ]thiophene-2-carboxylates, in accordance with the Fiesselmann thiophene synthesis protocol. Finally, the desired N,S-heterohexacenes were obtained by conversion of these fused 3-aminothiophene-2-carboxylates into the corresponding 3-aminothiophene intermediates, which acted as synthetic equivalents of thiophen-3(2 H)-ones, followed by their acid-promoted reaction with arylhydrazines, in accordance with the Fischer indolization procedure.