Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 48, Pages 11687-11695Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob01777g
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Funding
- University of Camerino (FAR)
- BI Research Italia
- Pfizer Global Supply - Ascoli Piceno Site
- delta Company
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The benzimidazole core is a common moiety in a large number of natural products and pharmacologically active small molecules. The synthesis of novel benzimidazole derivatives remains a main focus in medicinal research. In continuation of the efforts towards Ce(III) catalysts for organic transformations, we observed for the first time the activity of the iodide ion and copper cation in activating CeCl3 center dot 7H(2)O in the selective formation of prototypical 2-substituted benzimidazoles. The one-pot CeCl3 center dot 7H(2)O-CuI catalytic system procedure includes the cyclo-dehydrogenation of aniline Schiff's bases, generated in situ from the condensation of 1,2-phenylenediamine and aldehydes, followed by the oxidation with iodine, which works as a hydrogen sponge. Mild reaction conditions, good to excellent yields, and clean reactions make the procedure a useful contribution to the synthesis of biologically active fused heterocycles containing benzimidazoquinazolines.
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