Regioselective, Solvent- and Metal-Free Chalcogenation of Imidazo[1,2-a]pyridines by Employing I2/DMSO as the Catalytic Oxidation System

Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines were achieved by using diorganoyl dichalcogenides under solvent‐free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 %...

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Veröffentlicht in:Chemistry : a European journal 2016-08, Vol.22 (33), p.11854-11862
Hauptverfasser: Rafique, Jamal, Saba, Sumbal, Rosário, Alisson R., Braga, Antonio L.
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Sprache:eng
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Zusammenfassung:Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines were achieved by using diorganoyl dichalcogenides under solvent‐free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 % yield by using DMSO as an oxidant, in the absence of a metal catalyst, and under an inert atmosphere. This mild, green approach allowed the preparation of different types of chalcogenated imidazo[1,2‐a]pyridines with structural diversity. Furthermore, the current protocol was also extended to other N‐heterocyclic cores. Chalcogenation of N‐heterocycles: Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines are achieved by using diorganoyl dichalcogenides under solvent‐free conditions.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201600800