One-pot, microwave-assisted copper(i)-catalysed dithiocarbamation: facile introduction of dithiocarbamate on imidazopyridines

Abstract

A facile and proficient dithiocarbamation of imidazo[1,2-a]pyridines and other imidazoheterocycles with in situ generated dithiocarbamates is established using a water-soluble, stable copper(I) catalyst and molecular oxygen under microwave conditions. The reaction proceeds efficiently, tolerating a broad range of substrates, resulting in moderate to excellent yields. The intrinsic advantages of this one-pot process are the use of a greener solvent, a reduced reaction time, catalyst recyclability, scalability, and the high yields of the products. The in silico analysis revealed that all the synthesized derivatives have a drug-likeness and good ADME/T profile. In addition, the compounds 3be (IC₅₀ value: 7.28 ± 2.31 μM) and 3bb (IC₅₀ value: 10.20 ± 2.10 μM) were found to be more potent than the standard drug 5-fluorouracil (IC₅₀ value: 24.78 ± 0.08 μM) towards MCF-7 human breast cancer cells.