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2023 , Vol. 43 >Issue 11: 3888 - 3899

DOI: https://doi.org/10.6023/cjoc202303029

研究论文

基于原位形成的氮杂邻亚甲基苯醌和卤代萘酚的分子间[4＋1]螺环化/去芳香化反应

  • 梁俊秀 ,
  • 刘亚洲 ,
  • 王阿木 ,
  • 吴彦超 ,
  • 马小锋 ,
  • 李惠静
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  • 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

  网络出版日期: 2023-07-13

基金资助

国家自然科学基金(22001246); 国家自然科学基金(22271070)

收起

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

  • Junxiu Liang ,
  • Yazhou Liu ,
  • Amu Wang ,
  • Yanchao Wu ,
  • Xiaofeng Ma ,
  • Huijing Li
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  • 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
* E-mail: ;

Received date: 2023-03-20

  Revised date: 2023-06-16

  Online published: 2023-07-13

Supported by

National Natural Science Foundation of China(22001246); National Natural Science Foundation of China(22271070)

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摘要

报道了一种碱促进的卤代萘酚与N-(邻氯甲基)芳基酰胺[4＋1]螺环化/去芳构化策略, 以此来直接有效地合成氮杂螺环化合物. 在温和条件下以中等至优秀的收率、高非对映选择性地合成了一系列氮杂螺环化合物. 该反应可以兼容各种官能团, 如醛基、游离羟基和不同的N保护基, 如Bz和Ts等. 对产物进行了转化, 并提出了可能的反应机理.

关键词： 氮杂螺环; [4＋1]环加成反应; 脱芳构化; 螺环化

本文引用格式

梁俊秀 , 刘亚洲 , 王阿木 , 吴彦超 , 马小锋 , 李惠静 . 基于原位形成的氮杂邻亚甲基苯醌和卤代萘酚的分子间[4＋1]螺环化/去芳香化反应[J]. 有机化学, 2023 , 43(11) : 3888 -3899 . DOI: 10.6023/cjoc202303029

Abstract

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

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