KIO<sub>4</sub>‐mediated Selective Hydroxymethylation/Methylenation of Imidazo‐Heteroarenes: A Greener Approach
Marcelo S. Franco, Sumbal Saba, Jamal Rafique, Antônio L. Braga
Abstract
)-H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo[1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields.
Topics & Concepts
Ethylene glycolChemistryGlycerolReagentHydroxymethylFormaldehydeBond cleavageEthyleneCombinatorial chemistryOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSynthesis and Catalytic Reactions