有机化学 ›› 2019, Vol. 39 ›› Issue (7): 1970-1975.DOI: 10.6023/cjoc201901030 上一篇    下一篇

研究论文

氮氧烯丙基正离子与肟的[3+3]环加成反应:2-N-无取代-1,2,4-噁二嗪-5-酮类化合物的合成

张智勇, 王琦, 张浩, 陈永明, 王欣, 葛泽梅, 李润涛   

  1. 北京大学药学院 天然药物及仿生药物国家重点实验室 北京 100191
  • 收稿日期:2019-01-20 修回日期:2019-02-28 出版日期:2019-07-25 发布日期:2019-04-08
  • 通讯作者: 李润涛 E-mail:lirt@bjmu.edu.cn
  • 基金资助:

    国家自然科学基金(No.81673287)资助项目.

[3+3] Cycloaddition Reactions of Aza-oxyallyl Cations with Oximes: Synthesis of 2-N-Unsubstituted 1,2,4-Oxadiazinan-5-ones

Zhang Zhiyong, Wang Qi, Zhang Hao, Chen Yongming, Wang Xin, Ge Zemei, Li Runtao   

  1. a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191
  • Received:2019-01-20 Revised:2019-02-28 Online:2019-07-25 Published:2019-04-08
  • Contact: 10.6023/cjoc201901030 E-mail:lirt@bjmu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 81673287).

首次实现了肟与氮氧烯丙基正离子的[3+3]环加成反应,为2-N-无取代-1,2,4-噁二嗪-5-酮类化合物的合成提供了一种有效方法.该方法具有原料易得、反应条件温和及收率高等优点.

关键词: 1,2,4-噁二嗪-5-酮, α-溴代-N-苄氧基乙酰胺, 氮氧烯丙基正离子, 肟, [3+3]环加成

The first[3+3] cycloaddition reaction of in situ-generated aza-oxyallyl cations with oximes was developed. This approach provides a simple and efficient method for the synthesis of 2-N-unsubstituted 1,2,4-oxadiazin-5-one derivatives with many merits, such as easy available regents, mild reaction conditions and high yield.

Key words: 1,2,4-oxadiazinan-5-one, α-halohydroxamate, azaoxyallyl cations, oxime, [3+3]-cycloaddition