Details

Autor(en) / Beteiligte

• Trofimov, Boris A
• Volkov, Pavel A
• Khrapova, Kseniya O
• Telezhkin, Anton A
• Ivanova, Nina I
• Albanov, Alexander I
• Gusarova, Nina K
• Belogolova, Alexandra M
• Trofimov, Alexander B

Titel

Acetylene-Triggered Reductive Incorporation of Phosphine Chalcogenides into a Quinoline Scaffold: Toward S N H Ar Reaction

Ist Teil von

• Journal of organic chemistry, 2019-05, Vol.84 (10), p.6244-6257

Ort / Verlag

United States

Erscheinungsjahr

2019

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Quinolines react with acylacetylenes and secondary phosphine chalcogenides at 20-75 °C to afford N-acylvinyl-2(1)-chalcogenophosphoryldihydroquinolines in good and excellent yields. Unlike the pyridine-derived similar intermediates, which eliminate E-alkenes to give aromatic chalcogenophosphorylpyridines, thereby completing S Ar reaction, with quinolines, the reaction stops at the formation of the above phosphorylated N-acylvinyl-dihydroquinolines, thus representing a pendant S Ar process. This reaction opens a one-pot atom-economic single-step access to pharmaceutically targeted phosphorylated functionalized dihydroquinolines and isoquinolines.