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Transition-Metal-Free Approach to Acridone Derivatives by TBHP-Promoted Oxidative Annulation of Isatins with Arynes
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2023-05-29 , DOI: 10.1021/acs.joc.3c00250
Min Luo 1 , Nana Dong 1 , Mengyao Zhu 1 , Yongfeng Wang 1 , Cheng Xu 1 , Guodong Yin 1
Affiliation  

A tert-butyl hydroperoxide-promoted oxidative annulation reaction of isatins with 2-(trimethylsilyl)aryl triflates for the convenient synthesis of acridone derivatives has been established. Mechanistic investigation suggested that the reaction may proceed via consecutive Baeyer–Villiger-type rearrangement followed by an intermolecular cyclization. This synthetic approach offers several advantages, including broad substrate scope, good functional group tolerance, and simplicity of operation. Additionally, successful late-stage modification of the obtained compounds was achieved, expanding the application potential of this methodology in organic synthesis.

中文翻译:

通过 TBHP 促进靛红与芳烃的氧化环化制备吖啶酮衍生物的无过渡金属方法

建立了叔丁基过氧化氢促进的靛红与2-(三甲基甲硅烷基)芳基三氟甲磺酸酯的氧化成环反应,以方便合成吖啶酮衍生物机理研究表明该反应可能通过连续的Baeyer-Villiger型重排和随后的分子间环化进行。这种合成方法具有多种优点,包括广泛的底物范围、良好的官能团耐受性和操作简单。此外,还成功地对所得化合物进行了后期修饰,扩大了该方法在有机合成中的应用潜力。
更新日期:2023-05-29
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