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

• Roman A. Irgashev

Beilstein J. Org. Chem. 2025, 21, 2489–2497, doi:10.3762/bjoc.21.191

• Roman A. Irgashev Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, 620137, Russia 10.3762/bjoc.21.191 Abstract A versatile synthetic route to thieno[3,2-b]thiophenes was elaborated from dimethyl 3-nitrothiophene-2,5-dicarboxylate

• functionalized thieno[3,2-b]thiophenes with potential applications in pharmaceutical and materials chemistry. Keywords: aromatic nucleophilic substitution; disulfide derivative; 3-nitrothiophene; organic disulfides; thieno[3,2-b]thiophene; thiophene ring closure; Introduction Thieno[3,2-b]thiophene (TT

• TTs from the activated 3-nitrosubstituted thiophenes [29][30]. This strategy provides an effective access to the 3-hydroxy-TTs via the nucleophilic substitution of the nitro group in 3-nitrothiophene precursors using S-nucleophiles, such as alkyl thioglycolates or mercaptoacetone (Scheme 1, route V

Synthesis and characterization of S,N-heterotetracenes

• Astrid Vogt,
• Florian Henne,
• Christoph Wetzel,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2020, 16, 2636–2644, doi:10.3762/bjoc.16.214

• a Pd-catalyzed Stille-type cross-coupling with 2-bromo-3-nitrothiophene (15) to precursor 2-(3-nitrothien-2-yl)thieno[3,2-b]thiophene (16) in 64% yield. Cadogan cyclization of nitro derivative 16 with triethyl phosphite at reflux gave 4H-thieno[3,2-b]thieno[2’, 3’:4,5]thieno[2,3-d]pyrrole (H-SN4, 13

An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

• Sundaravel Vivek Kumar,
• Shanmugam Muthusubramanian,
• J. Carlos Menéndez and
• Subbu Perumal

Beilstein J. Org. Chem. 2015, 11, 1707–1712, doi:10.3762/bjoc.11.185

• associated with the lack of regioselectivity and difficult isomer separation [23]. Other methods for the synthesis of 2,3-disubsituted thiophenes include the reactions of (i) 1,4-dithiane-2,5-diol with nitroalkenes [24], activated nitriles [25] and cyanoacetamide [26]; (ii) 3-nitrothiophene with Grignard

• formation of 3. Optimization of the synthesis of compound 3ea. Scope of the 2-amino-3-nitrothiophene synthesis. Supporting Information Supporting Information File 296: Experimental procedures, characterization data, details of the NMR structural determination of 3c and copies of 1H NMR, 13C NMR and ESI