Beilstein Arch. 2025, 202552. https://doi.org/10.3762/bxiv.2025.52.v1
Published 26 Aug 2025
A versatile synthetic route to thieno[3,2-b]thiophenes was elaborated from dimethyl 3-nitrothiophene-2,5-dicarboxylate. Nucleophilic substitution of the nitro group with sulfur nucleophiles, including thioacetate or disulfide anions as well as thioacetamide, yielded bis(thiophen-3-yl) disulfide and sulfide derivatives. The disulfide served as a suitable precursor for the preparation of 3-alkylthio-substituted thiophene-2,5-dicarboxylates by its one-pot reduction-alkylation using NaBH4 in DMF followed by an alkylating agent. Base-promoted cyclization of electron-deficient 3-alkylthio derivatives furnished 2-aryl-, 2-aroyl-, and 2-cyano-substituted thieno[3,2-b]thiophenes, bearing 3-hydorxy group. This protocol broadens access to functionalized thieno[3,2-b]thiophenes with potential applications in pharmaceutical and materials chemistry.
Keywords: thieno[3,2-b]thiophene; thiophene ring closure; 3-nitrothiophene; organic disulfides, aromatic nucleophilic substation; disulfide derivative
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Irgashev, R. A. Beilstein Arch. 2025, 202552. doi:10.3762/bxiv.2025.52.v1
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© 2025 Irgashev; licensee Beilstein-Institut.
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