1359619-04-7Relevant academic research and scientific papers
Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles
Dvorko, Marina Yu.,Schmidt, Elena Yu.,Glotova, Tatyana E.,Shabalin, Dmitrii A.,Ushakov, Igor A.,Kobychev, Vladimir B.,Petrushenko, Konstantin B.,Mikhaleva, Al'Bina I.,Trofimov, Boris A.
experimental part, p. 1963 - 1971 (2012/03/22)
A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90-120 °C, 5-13 h). Thermodynamically controlled E/Z-isomer ratio of 1-styrylpyrroles depends on structure of both pyrroles and acetylenes ranging from ca. 100% E-stereoselectivity (for the pair unsubstituted pyrrole - phenylacetylene) to 90, 96% Z-stereoselectivity (for the pairs: 2-phenylpyrrole - phenylacetylene and 2-(2-thienyl)pyrrole - phenylacetylene, respectively).
