Synthesis of Novel 1,2,3-Triazole/Isoxazole-Functionalized Imidazo[4,5-b]pyridin-2(3H)-one Derivatives, Their Antimicrobial and Anticancer Activity

Abstract

A series of novel 1,2,3-triazole/isoxazole-functionalized imidazo[4,5-b]pyridine-2(3H)-one derivatives 7 and 8 were prepared starting from pyridin-2(1H)-one 1 in a series of steps. Initially, compound 1 was converted into imidazo[4,5-b]pyridine-2(3H)-one 5 via formation of 2-alkylamino/amino-6-phenyl-4-(trifluoromethyl)nicotinonitrile 3 followed by hydrolysis 4 and Hoffman type rearrangement 5. Compound 5 was further reacted with propargyl bromide to form exclusively N-propargylated derivatives 6. Compounds 6 were cyclized with arylazides/aryloximes in the presence of CuI and sodium hypochlorite, respectively, and obtained title products 7 and 8. All the final products 7 and 8 were screened for antimicrobial and anticancer activity.