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

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 4p and 4q showed the maximum fluorescence quantum yield (0.36) in water medium under basic conditions and compound 4c showed the maximum fluorescence quantum yield (0.75) in DMSO medium.

Automated summary

A metal-free one-pot three-component reaction for the synthesis of pyrimidine-linked imidazopyridines using aryl methyl ketones, 2-aminopyridines, and barbituric acids was reported. The reaction was catalyzed by a small amount of molecular iodine in DMSO medium and involved C-H oxidation and the formation of one C-C and two C-N bonds. Various aryl methyl ketones and 2-aminopyridines were found to be suitable substrates. The synthesized products exhibited good to excellent UV and fluorescence properties, with compounds 4p and 4q showing the highest fluorescence quantum yield (0.36) in water medium under basic conditions, and compound 4c showing the highest fluorescence quantum yield (0.75) in DMSO medium.