B. Trofimov, P. Volkov, A. Telezhkin
Mar 12, 2020
Citations
0
Influential Citations
7
Citations
Journal
The Journal of organic chemistry
Abstract
Quinolines undergo catalyst-free double CH-functionalization upon treatment with secondary phosphine oxides (70-75 °C, 20-48 h) followed by oxidation of the intermediate 2,4-bisphosphoryltetrahydroquinolines with chloranil. The yields of the target 2,4-bisphosphorylated quinolines are up to 77%. Thus, double SNHAr reaction sequence in the same molecule of quinoline has been realized. In case of 2,4-bisphenylphosphoryltetrahydroquinolines, the aromatization occurs with elimination of one molecule of diphenylphosphine oxide to afford the products of monofunctionalization, 4-diphenylphosphorylquinolines in 40-45% yields.