Beyond classic acetylene chemistry: base-mediated self-organization of acetylenes with nitriles toward rarely functionalized dihydropyridinimines

Abstract

Herein, we disclose that two molecules of (het)arylacetylenes and two molecules of aliphatic nitriles readily undergo organization in the KOBu^t/DMSO system at 40 °C, forming dihydropyridines bearing imine, acetylenic, (het)aromatic and aliphatic substituents in up to 77% yield. This unprecedented reaction highlights the generality of the recently discovered self-organization of complex molecules where several acetylene units combine with simple nucleophiles, a phenomenon steered by acetylenic carbanions.