Work

Assembly strategy for thieno[3,2- b ]thiophenes via a disulfide intermediate derived from 3-nitrothiophene-2,5-dicarboxylate

Year: 2025

Type: article

Abstract: 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 NaBH 4 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 a 3-hydroxy group. This protocol broadens access to functionalized thieno[3,2- b ]thiophenes with potential applications in pharmaceutical and materials chemistry.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.21.191

Author: Roman A Irgashev

Institutions: Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Language: English

Topic: Synthesis of heterocyclic compounds

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Ural Branch, Russian Academy of Sciences, Russian Science Foundation, Russian Academy of Sciences, Postovsky Institute of Organic Synthesis

Award: G7442276595