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.