有机化学 ›› 2024, Vol. 44 ›› Issue (7): 2223-2232.DOI: 10.6023/cjoc202403012 上一篇    下一篇

研究论文

铑催化3-芳基-2H-1,4-苯并噁嗪与重氮萘-2H-酮的[3+3]环化合成螺吡喃化合物

温梦柯a,b, 李宜越b, 杜浩康b, 陈章培a,*(), 杨西发b,*()   

  1. a 东北大学理学院化学系 辽宁沈阳 110819
    b 河南农业大学植物保护学院农药系 郑州 450002
  • 收稿日期:2024-03-10 修回日期:2024-04-02 发布日期:2024-04-24
  • 基金资助:
    国家自然科学基金(22201066); 河南省科技攻关(222102110259)

Synthesis of Spiropyrans via Rh(III)-Catalyzed [3+3] Cyclization of 3-Aryl-2H-1,4-benzoxazine and Diazonaphthalene-2H-ones

Mengke Wena,b, Yiyue Lib, Haokang Dub, Zhangpei Chena(), Xifa Yangb()   

  1. a Department of Chemistry, College of Sciences, Northeastern University, Shenyang, Liaoning 110819
    b Department of Pesticide Science, College of Plant Protection, Henan Agricultural University, Zhengzhou, Henan 450002
  • Received:2024-03-10 Revised:2024-04-02 Published:2024-04-24
  • Contact: E-mail: chenzhangpei@mail.neu.edu.cn;yangxifachem@163.com
  • Supported by:
    National Natural Science Foundation of China(22201066); Science and Technology Planning Project of Henan Province(222102110259)

通过Rh(III)催化3-芳基-2H-1,4-苯并噁嗪与重氮萘-2H-酮的1∶1偶联环化合成了一系列含NH的螺吡喃化合物, 该反应经C—H键活化随后发生[3+3]环化得到目标产物, 表现出良好的官能团耐受性. 同时, 对反应机理进行了初步探索, 并提出了相应的催化循环机理.

关键词: 螺吡喃化合物, 三价铑, 碳氢键活化, 苯并噁嗪, 重氮萘-2H-酮

Rh(III)-catalyzed 1∶1 coupling of 3-aryl-2H-benzo[b][1,4]oxazines with diazonaphthalene-2H-ones has been realized for mild synthesis of NH-containing spiropyrans. The reaction proceeded via C—H activation followed [3+3] annulation with decent functional group tolerance. Preliminary mechanistic studies have been conducted and a plausible mechanism has been proposed.

Key words: spiropyrans, Rh(III), C—H activation, benzoxazines, diazonaphthalen-2H-ones