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Regioselective, Solvent‐ and Metal‐Free Chalcogenation of Imidazo[1,2‐ a ]pyridines by Employing I 2 /DMSO as the Catalytic Oxidation System
Author(s) -
Rafique Jamal,
Saba Sumbal,
Rosário Alisson R.,
Braga Antonio L.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600800
Subject(s) - regioselectivity , catalysis , chemistry , solvent , metal , medicinal chemistry , combinatorial chemistry , organic chemistry
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.