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Updated: May 13, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Beyond classic acetylene chemistry: base-mediated self-organization of acetylenes with nitriles toward rarely
Inna V Tatarinova1, Natal'ya A Lobanova1, Igor A Ushakov1
1A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia. boris_trofimov@irioch.irk.ru.
Abstract:
Herein, we disclose that two molecules of (het)arylacetylenes and two molecules of aliphatic nitriles readily undergo organization in the KOBu/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.
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