Base-Catalyzed [3 + 2] Cycloaddition of<i>N-</i>Benzyl Ketimines to Arylacetylenes Followed by Oxidation: A One-Pot Access to Polyarylated 2<i>H</i>-Pyrroles via Intermediate Pyrrolines
Ivan A. Bidusenko, Elena Yu. Schmidt, Igor А. Ushakov, Alexander V. Vashchenko, Б. А. Трофимов
Abstract
N-Benzyl ketimines undergo [3 + 2] cycloaddition with arylacetylenes in the KOBut/DMSO solution to 2,3,5-triarylpyrrolines, which are oxidized (chloranil, DDQ) in situ to 2,3,5-triaryl-2H-pyrroles in 53–71% yields. The intermediate 1-pyrrolines can be isolated in 31–91% yields and separately oxidized to the corresponding 2H-pyrroles.
Topics & Concepts
ChemistryCycloadditionChloranilCatalysisMedicinal chemistryBase (topology)Organic chemistryMathematicsMathematical analysisSynthesis and Characterization of PyrrolesOxidative Organic Chemistry ReactionsOrganic Chemistry Cycloaddition Reactions