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Synthesis of 1,2,4-Benzotriazines via Copper(I) Iodide/1H-Pyrrole-2-carboxylic Acid Catalyzed Coupling of o-Haloacetanilides and N-Boc Hydrazine

Yijun Zhou, Zhigao Zhang, Yongwen Jiang, Xianhua Pan, Dawei Ma*

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China, Email: madwmail.sioc.ac.cn

Y. Zhou, Z. Zhang, Y. Jiang, X. Pan, D. Ma, Synlett, 2015, 26, 1586-1590.

DOI: 10.1055/s-0034-1378708 (free Supporting Information)


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Abstract

A Cu-catalyzed coupling of o-haloacetanilides and N-Boc hydrazine and a subsequent oxidation proceeded at room temperature to afford azo compounds. Deprotection with TFA and in situ cyclization gives 1,2,4-benzotriazines.

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Key Words

coupling, cyclization, copper, catalysis, 1,2,4-benzotriazines


ID: J60-Y2015