1248342-77-9Relevant academic research and scientific papers
Diastereoselective synthesis of CF3-oxazinoquinolines in water
Muzalevskiy, Vasiliy M.,Belyaeva, Kseniya V.,Trofimov, Boris A.,Nenajdenko, Valentine G.
, p. 6353 - 6360 (2019)
A highly efficient stereoselective synthesis of CF3-oxazinoquinolines was elaborated using the reaction of CF3-ynones with quinolines in water. It was demonstrated that under these green conditions, the reaction proceeds up to 20 times faster to provide target compounds in almost quantitative yields. Moreover, this method is devoid of any chromatographic purification to give CF3-oxazinoquinolines with complete diastereoselectivity. The presented eco-friendly approach was found much more efficient than standard reactions in organic solvents. The synthetic utility of the prepared CF3-oxazinoquinolines was demonstrated.
Organometal-Free Arylation and Arylation/Trifluoroacetylation of Quinolines by Their Reaction with CF3-ynones and Base-Induced Rearrangement
Muzalevskiy, Vasiliy M.,Belyaeva, Kseniya V.,Trofimov, Boris A.,Nenajdenko, Valentine G.
, p. 9993 - 10006 (2020/09/09)
The reaction of quinolines with CF3-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield. As a result, unusual rearrangement of 1,3-oxazinoquinolines to form either 2-arylquinolines or 2-aryl-3-trifluoroacetylquinolines was discovered. The decisive role of the base in the reaction direction was shown. Using these reactions, highly efficient pathways to 2-arylquinolines and 2-aryl-3-trifluoroacetylquinolines were elaborated to provide the corresponding compounds in high yields using a simple one-pot procedure. The possible mechanism of rearrangement is discussed.
