A three-component synthesis of aryl(heteroaryl)acylamides.
A three-component reaction of azole or azine N-oxides, 1,1-difluorostyrenes and amines gives amides of α-aryl-α-heteroarylacetic or propionic acids. The key step is 1,3-dipolar cycloaddition between N-oxide and difluorostyrene leading to the acyl fluoride intermediate, which has been identified and characterized by NMR spectroscopy. The whole process is an example of selective functionalization of C-H bonds in both 5- and 6-membered heterocyclic systems.
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw 42, Poland. rafal.loska@icho.edu.pl.
Rafał
R
Loska
Patrycja
P
Bukowska