Journal
SYNTHESIS-STUTTGART
Volume 54, Issue 14, Pages 3227-3238Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1799-9339
Keywords
conjugation; cyclization; fused-ring system; heterocycles; amines; azides
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Funding
- Russian Science Foundation [20-73-10043]
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This article discusses the development of practical methods for synthesizing 4-azido-5-arylthiophene-2-carboxylates and 4-amino-5-arylthiophene-2-carboxylates using the Fiesselmann reaction. The decomposition of 4-azido-5-arylthiophene-2-carboxylates through photochemical and thermal processes, including microwave-assisted decomposition, was studied to synthesize fused 4H-thieno[3,2-b]pyrrole derivatives. These proposed methods allow for the synthesis of functionalized heteroacenes, which are important building blocks for organic semiconductors.
This article is focused on the development of practical approaches to the synthesis of 4-azido-5-arylthiophene-2-carboxylates and 4-amino-5-arylthiophene-2-carboxylates using the Fiesselmann reaction. The photochemical and thermal (including microwave-assisted) decomposition of 4-azido-5-arylthiophene-2-carboxylates have been studied in order to synthesize fused 4H-thieno[3,2-b]pyrrole derivatives. The proposed approaches allow to obtain functionally substituted heteroacenes, which are of interest as building blocks for organic semiconductors.
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