Enzymatic oxidative polymerization of aminochalcones by use of horseradish peroxidase

The synthesis of six different aminochalcones, 3-(4-aminophenyl)-1-phenyl-2-propen-1-one (3a), 3-(4-aminophenyl)-1-(4-ethoxyphenyl)-2-propen-1-one (3b), 3-(4-aminophenyl)-1-(4-fluorophenyl)-2-propen-1-one (3c), 3-(4-aminophenyl)-1-(2,3,4,5,6-pentafluorophenyl)-2-propen-1-one (3d), 1-(4-aminophenyl)-3-phenyl-2-propen-1-one (4a), 1-(4-aminophenyl)-3-(9-anthryl)-2-propen-1-one (4b), and a complex 3a/2,6-dimethyl-β-cyclodextrin (3e) is described. Enzymatically catalyzed oxidative polymerization in presence of horseradish peroxidase/H2O2 system was observed in case of 3a and 3b. The oligomeric products were characterized by NMR, IR spectroscopy and thermal analysis.