Sequential Regioselective Diorganochalcogenations of Imidazo[1,2-<i>a</i>]pyrimidines Using I<sub>2</sub>/H<sub>3</sub>PO<sub>4</sub> in Dimethylsulfoxide
Anne Roly Obah Kosso, Youssef Kabri, Julie Broggi, Sébastien Redon, Patrice Vanelle
Abstract
The dichalcogenation of imidazoheterocycles led to the first functionalization of imidazo[1,2-a]pyrimidine cores on the C6-position. The methodology, involving iodine/dimethylsulfoxide oxidation of diaryldichalcogenides, started with C3-chalcogenation, followed by C6 selanylation, activated in acidic medium. This novel sequential dichalcogenation strategy proceeded efficiently with excellent regioselectivity and yields.
Topics & Concepts
RegioselectivityChemistryPyrimidineIodineSurface modificationMedicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryCatalysisPhysical chemistryOrganoselenium and organotellurium chemistrySulfur-Based Synthesis TechniquesVanadium and Halogenation Chemistry