Affiliation:
1. Department of Organic Chemistry, Omsk F. M. Dostoevsky State University
2. Laboratory of New Organic Materials, Omsk State Technical University
Abstract
AbstractA new approach to the synthesis of fused benzothiophene derivatives was developed based on iodine-promoted photocyclization of 4,5-diaryl-substituted thiophenes obtained in three steps from commercially available compounds. Comparative analysis showed that photochemical cyclization is a more efficient method for the preparation of fused benzo[b]thiophene derivatives, compared to oxidative coupling of 4,5-diaryl-substituted thiophenes in the presence of iron(III) chloride and palladium-catalyzed intramolecular arylation. This new approach provides an efficient synthesis of functionally substituted naphtho[2,1-b:3,4-b′]dithiophenes, phenanthro[9,10-b]thiophenes, benzo[1,2-b:3,4-b′:6,5-b′′]trithiophenes, as well as new fused heterocycles containing a pyridine ring and/or a carbazole moiety.
Funder
Russian Science Foundation
Subject
Organic Chemistry,Catalysis
Cited by
5 articles.
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1. Synthesis, Photophysical, and (Spectro)Electrochemical Properties of New Benzo[1,2-c][1,2,5]thiadiazoles and Benzo[1,2-d][1,2,3]triazoles Fused with Two Thiazole Rings;The Journal of Organic Chemistry;2023-04-18
2. The effect of electron-donating moiety structure on the electrochemical and photophysical properties of dithiophene- and naphtho[2,1-b:3,4-b']dithiophene-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles;Chemistry of Heterocyclic Compounds;2023-02
3. Five-membered ring systems: thiophenes and selenium/tellurium analogs and benzo analogs;Progress in Heterocyclic Chemistry;2023
4. Synthesis of New Fused 4H-Thieno[3,2-b]pyrrole Derivatives via Decomposition of Methyl 4-Azido-5-arylthiophene-2-carboxylates;Synthesis;2022-03-16
5. Synthesis and Evaluation of 3-Halobenzo[b]thiophenes as Potential Antibacterial and Antifungal Agents;Pharmaceuticals;2021-12-28