Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines

Abstract

Herein, we report a metal-free one-pot three-component reaction of aryl methyl ketones, 2-aminopyridines, and barbituric acids for the synthesis of pyrimidine-linked imidazopyridines using a catalytic amount of molecular iodine in DMSO medium. This process involves a one-pot C-H oxidation, followed by the formation of one C-C and two C-N bonds. A wide variety of aryl methyl ketones and 2-aminopyridines were found to be suitable for this methodology. The UV and fluorescence properties of the synthesized products were studied in water and DMSO media. Most of the synthesized products exhibited very good to excellent fluorescence quantum yield. Among all the products, compounds <b>4p</b> and <b>4q</b> showed the maximum fluorescence quantum yield (0.36) in water medium under basic conditions and compound <b>4c</b> showed the maximum fluorescence quantum yield (0.75) in DMSO medium.