13800-28-7Relevant academic research and scientific papers
The rearrangement of tosylated flavones to 1′-(alkylamino)aurones with primary amines
Kandioller, Wolfgang,Kubanik, Mario,Bytzek, Anna K.,Jakupec, Michael A.,Roller, Alexander,Keppler, Bernhard K.,Hartinger, Christian G.
, p. 8953 - 8959 (2015)
A rearrangement of 3-tosylflavone to the corresponding 1′-(alkylamino)aurone proceeds under mild conditions in the presence of primary amines in high yields. The reaction is applicable to different substituted 3-tosylflavones and alkyl amines and the respective aurones were isolated as a mixture of E/Z isomers. Further conversion of 1′-(methylamino)aurone to the corresponding thionated compound was performed by reaction with Lawesson's reagent and only the E isomer was obtained. This observation can be explained by the weaker exocyclic double bond, which facilitates rotation and the formation of the thermodynamically preferred E form. The characterization, preliminary biological investigations of the synthesized compounds and lipophilicity studies are discussed.
