Abstract
- The reactivity of 4-bromoacetyl-1H-1,2,3-triazoles towards amines and phenols was studied. Reaction of 4-bromoacetyl-1H-1,2,3-triazole (1a; R = H) with benzylamine (2) in the absence of any catalyst unexpectedly afforded heterocycle 2,5-bis(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)pyrazine (4) in 50% yield. Additionally, the reaction of 1b (R = Br) with 4-bromoaniline and of 1c (R = Me) or 1d (R = NO2) with 1H-benzotriazole in basic media gave the expected aminoketone products 8 and 9a or 9b in high yields. Furthermore, the reaction of 1c (R = Me) or 1e (R = Cl) with phenol or ?-naphthol in basic media led to the production of keto-ethers 10 or 11, respectively in an excellent yield. Compound 10 showed the highest inhibitory effect against the growth of the tested pathogens.