Synthesis of 2-aryl-2H-[1,2,4]triazoloquinolin-3-one and 2-aryl-2H-[1,2,4]triazoloisoquinolin-3-one derivatives from α-chloroformylarylhydrazines hydrochloride

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• 作者：Jiann-Jyh Huang ; Kun-Lung Chen ; Yu-Shiang Lin ; Sheng-Chuan Yang ; Shih-Hsien Chuang ; Kuo-Chen Chiang ; Wen-Che Tseng ; Fung Fuh Wong ; Mou-Yung Yeh
• 关键词：α ; -Chloroformylarylhydrazine hydrochloride ; Quinoline ; Triazoloquinolin-3-one ; Triazoloisoquinolin-3-one
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：23 January 2010
• 年：2010
• 卷：66
• 期：4
• 页码：930-934
• 全文大小：286 K

文摘

The reaction of α-chloroformylarylhydrazines hydrochloride with quinoline under air provided the corresponding 2-aryl-2H-[1,2,4]triazoloquinolin-3-ones 3a–3d in 33–42 % yields and unexpected isomeric 2-aryl-2H-[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-2H-[1,2,4]triazoloisoquinolin-3-ones (4).