Acetylene-Triggered Reductive Incorporation of Phosphine Chalcogenides into a Quinoline Scaffold: Toward SNHAr Reaction

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

doi:10.1021/acs.joc.9b00519

Acetylene-Triggered Reductive Incorporation of Phosphine Chalcogenides into a Quinoline Scaffold: Toward S_N^HAr Reaction

J Org Chem. 2019 May 17;84(10):6244-6257. doi: 10.1021/acs.joc.9b00519. Epub 2019 Apr 30.

Authors

Boris A Trofimov¹, Pavel A Volkov¹, Kseniya O Khrapova¹, Anton A Telezhkin¹, Nina I Ivanova¹, Alexander I Albanov¹, Nina K Gusarova¹, Alexandra M Belogolova¹, Alexander B Trofimov¹

Affiliation

¹ A.E. Favorsky Irkutsk Institute of Chemistry , Siberian Branch of the Russian Academy of Sciences , 1 Favorsky Street , Irkutsk 664033 , Russian Federation.

PMID: 30999755
DOI: 10.1021/acs.joc.9b00519

Abstract

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_N^HAr reaction, with quinolines, the reaction stops at the formation of the above phosphorylated N-acylvinyl-dihydroquinolines, thus representing a pendant S_N^HAr process. This reaction opens a one-pot atom-economic single-step access to pharmaceutically targeted phosphorylated functionalized dihydroquinolines and isoquinolines.

Publication types

Research Support, Non-U.S. Gov't