有机化学 ›› 2023, Vol. 43 ›› Issue (11): 3997-4002.DOI: 10.6023/cjoc202304017 上一篇    下一篇

研究论文

PPh3-促进邻炔基硝基苯合成3-羟基-2-吲哚酮

赵雪纯, 樊辉, 徐瑶, 廖小铭, 张小祥*()   

  1. 南京林业大学化学工程学院 南京 210037
  • 收稿日期:2023-04-13 修回日期:2023-06-05 发布日期:2023-06-13
  • 基金资助:
    江苏省自然科学基金(BK20171449)

PPh3-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes

Xuechun Zhao, Hui Fan, Yao Xu, Xiaoming Liao, Xiaoxiang Zhang()   

  1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037
  • Received:2023-04-13 Revised:2023-06-05 Published:2023-06-13
  • Contact: E-mail: zhangxiaoxiang@njfu.edu.cn
  • Supported by:
    Natural Science Foundation of Jiangsu Province-Grants(BK20171449)

3-羟基-2-吲哚酮核心结构在合成化学和药物化学中都具有重要的意义. 发现了一种新的、有效的由邻炔基硝基芳烃制备3-羟基-2-吲哚酮的碱促进方法, 该反应可在不含过渡金属的条件下进行. 对各种邻炔基硝基芳烃进行测定, 并以中等至良好的产率获得所需的产物. 由三苯基膦引发的Wittig反应和随后的偶姻重排构成了主要的反应过程.

关键词: PPh3, Wittig反应, 3-羟基-2-吲哚酮, 邻炔基硝基

The 3-hydroxy-2-oxindole core structure is of considerable significance in both synthetic and medicinal chemistry. A novel and efficient base-promoted method for the preparation of 3-hydroxy-2-oxindoles from o-alkynylnitroarenes has been discovered. The reaction could be conducted under transition metal free conditions. Various o-alkynylnitroarenes were checked and the desired products were obtained in moderate to good yields. The Wittig-like reaction triggered by the PPh3 and the subsequent acyloin rearrangement constituted the main reaction process.

Key words: PPh3, Wittig reaction, 3-hydroxy-2-oxindoles, o-alkynylnitroarenes