Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3888-3899.DOI: 10.6023/cjoc202303029 Previous Articles     Next Articles


梁俊秀a,b, 刘亚洲b, 王阿木b, 吴彦超a, 马小锋b,*(), 李惠静a,*()   

  1. a 哈尔滨工业大学化工与化学学院 威海海洋生物医药产业技术研究院 哈尔滨 150006
    b 中国科学院成都生物研究所天然产物研究中心 成都 610041
  • 收稿日期:2023-03-20 修回日期:2023-06-16 发布日期:2023-07-12
  • 基金资助:
    国家自然科学基金(22001246); 国家自然科学基金(22271070)

Dearomatization of Halonaphthols via an Intermolecular [4+1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides

Junxiu Lianga,b, Yazhou Liub, Amu Wangb, Yanchao Wua, Xiaofeng Mab(), Huijing Lia()   

  1. a Weihai Marine Organism & Medical Technology Research Institute, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150006
    b Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041
  • Received:2023-03-20 Revised:2023-06-16 Published:2023-07-12
  • Contact: E-mail:;
  • Supported by:
    National Natural Science Foundation of China(22001246); National Natural Science Foundation of China(22271070)

A base promoted dearomatization strategy for [4+1] spiroannulation of halonaphthols with N-(o-chloromethyl) aryl amides is reported, which is used to efficiently synthesize azaspirocycles. A range of azaspirocycles were obtained in satisfactory to excellent yield with high diastereoselectivity under mild conditions. Variety functional groups including aldehyde and free hydroxyl group, and different N-protecting groups, such as Bz and Ts are compatibility. The transformation of the product and a possible mechanism were also provided.

Key words: azaspirocyclic compound, [4+1] cycloaddition reaction, dearomatization, spiroannulation