Abstract
The reaction of α-chloroformylarylhydrazines hydrochloride with quinoline under air provided the corresponding 2-aryl-2 H-[1,2,4]triazoloquinolin-3-ones 3a– 3d in 33–42% yields and unexpected isomeric 2-aryl-2 H-[1,2,4]triazoloisoquinolin-3-ones 4a– 4d in 30–42% yields. These two isomers were isolated and fully characterized by spectroscopic methods including X-ray crystallography. By employing 3-methylquinoline as the starting material under the same condition, the reaction only gave compound 3e– 3h as sole products in 70–82% yields without the formation of isomers. A plausible mechanism was proposed through electrophilic aromatic reaction, the tandem ring cyclization and ring-opening, and oxidation for the generation of 2-aryl-2 H-[1,2,4]triazoloisoquinolin-3-ones ( 4).
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