A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes
Никита Е. Голанцов, Alexandra S. Golubenkova, Alexey А. Festa, А. В. Варламов, Leonid G. Voskressensky
Abstract
The reaction of 1,2-disubstituted 2-imidazolines with electron-deficient alkynes proceeds as a pseudo-three-component process and forms imidazolidines with an N-vinylpropargylamine fragment. Heating the resulting imidazolidines in xylene on air leads to an effective formation of polysubstituted pyrroles through a domino sequence of aza-Claisen rearrangement/transannular nucleophilic addition/oxidative ring opening reactions. The direct one-pot transformation of 2-imidazolines to pyrroles has been also realized.
Topics & Concepts
ChemistryDominoNucleophileRing (chemistry)Cascade reactionMedicinal chemistryNucleophilic additionOxidative phosphorylationCombinatorial chemistryOrganic chemistryCatalysisBiochemistrySynthesis and Characterization of PyrrolesSynthesis of heterocyclic compoundsCatalytic C–H Functionalization Methods