An Effective Route to Dithieno[3,2-b:2′,3′-d]thiophene-Based Hexaheteroacenes

February 24, 2021Synlett

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Key Points

To establish an efficient synthetic methodology for accessing dithieno[3,2-b:2′,3′-d]thiophene-fused hexaheteroacenes from accessible starting materials.
Treated starting benzo[b]thieno[2,3-d]thiophen-3(2H)-ones with Vilsmeier reagent and hydroxylamine hydrochloride to yield 3-chlorobenzo[b]thieno[2,3-d]thiophene-2-carbonitriles.
Conducted Fiesselmann thiophene synthesis by reacting the carbonitriles with methyl sulfanylacetate to generate methyl 3-aminothiophene-2-carboxylate intermediates.
Converted the aminothiophene carboxylates into synthetic equivalents of thiophen-3(2H)-ones, followed by acid-promoted Fischer indolization with arylhydrazines.
Successfully synthesized a series of 12H-[1]benzo[4′′,5′′]thieno[2′′,3′′:4′,5′]thieno[2′,3′:4,5]thieno[3,2-b]indoles in three chemical steps.
Demonstrated that fused 3-aminothiophene-2-carboxylates serve as effective synthetic equivalents of thiophen-3(2H)-ones for acid-mediated Fischer indolization.

Chemical synthesis study demonstrates a three-step route to N,S-heterohexacenes, indicating an efficient pathway to fused heteroacene frameworks.

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Иргашев et al. (2021) studied this question.

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