Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles
Elena Yu. Schmidt, Nadezhda V. Semenova, Elena V. Ivanova, Ivan A. Bidusenko, Б. А. Трофимов
Abstract
A new superbase-promoted reaction of acetylene involves self-organization of its three molecules with one molecule of arylamine in KOH/DMSO system to afford 1-aryl-2,5- dimethylpyrroles in up to 63% yields. The key step of this reaction cascade is assumed to be the nucleophilic addition of acetylene to the C = N bond of the intermediate aldimine (aza-Favorsky reaction).
Topics & Concepts
ChemistryAcetyleneSuperbaseNucleophilic additionAldimineArylNucleophileMoleculeOrganic chemistryCombinatorial chemistryMedicinal chemistryComputational chemistryPhotochemistryCatalysisAlkylSynthesis and Characterization of PyrrolesChemical Synthesis and AnalysisFluorine in Organic Chemistry