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Synthesis of 1,2,4-benzotriazines

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