Tandem C鈥揙 and C鈥揘 Bonds Formation Through O-Arylation and [3,3]-Rearrangement by Diaryliodonium Salts: Synthesis of N-Aryl Benzo[1,2,3]triazin-4(1H)-one Derivatives

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• 作者：Wei-Min Shi ; Xiao-Pan Ma ; Cheng-Xue Pan ; Gui-Fa Su ; Dong-Liang Mo
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：80
• 期：21
• 页码：11175-11183
• 全文大小：505K
• ISSN：1520-6904

文摘

Metal-free O-arylation and [3, 3]-rearrangement have been shown as an efficient strategy to construct new C鈥揙 and C鈥揘 bonds in one-pot reactions. The method was used to prepare N-aryl benzo[1,2,3]triazin-4(1H)-one derivatives in good yields from N-hydroxy benzo[1,2,3]triazin-4(3H)-one and diaryliodonium salts. The reaction was tolerated a variety of sensitive functional groups such as iodine, nitro, ester, and aldehyde groups. A rational mechanism was proposed based on the experimental results, and the reaction was easily up to gram scale.