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Peer reviewed
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Elena Yu Schmidt; Tatarinova, Inna V; Lobanova, Natal'ya A; Ushakov, Igor A; Irina Yu Bagryanskaya; Trofimov, Boris A
Organic & biomolecular chemistry, 09/2023, Volume: 21, Issue: 35Journal Article
We have discovered that three molecules of arylacetylene are rapidly (15 min) assembled with one molecule of nitrile at room temperature in the KOBut/DMSO system to afford 2-aryl-3-arylethynyl-4-aryl-5-benzyl-1H-pyrroles in up to 76% yield. We assume that this unprecedented self-organization process involves the cascade addition of acetylenic carbanions, first to the C≡N, then to the C≡C and C=C bonds of the intermediates, followed by pyrrole ring closure via the intramolecular nucleophilic addition of the NH functional group to the C≡C bond of the final intermediates.
