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2021 , Vol. 41 >Issue 4: 1622 - 1630

DOI: https://doi.org/10.6023/cjoc202010041

研究论文

三乙胺促进的环丙烯酮和α-卤代异羟肟酸酯的环化反应合成多取代6H-1,3-噁嗪-6-酮

  • 刘思展 ,
  • 崔明月 ,
  • 王博文 ,
  • 胡春梅 ,
  • 郑莹莹 ,
  • 李晶 ,
  • 徐学涛 ,
  • 王震 ,
  • 王少华
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  • a 兰州大学药学院 兰州 730000
    b 五邑大学生物科技与大健康学院 广东江门 529020

收稿日期: 2020-10-30

  修回日期: 2020-12-10

  网络出版日期: 2020-12-24

基金资助

国家自然科学基金(21472077); 国家自然科学基金(21772071); 广东省教育厅(2017KTSCX185); 广东省教育厅(2017KSYS010); 广东省教育厅(2019KZDXM035)

收起

Triethyl Amine-Promoted Cyclization Reaction between Cyclopropenone and α-Halogenated Hydroxamate for the Synthesis of Polysubstituted 6H-1,3-Oxazin-6-one

  • Sizhan Liu ,
  • Mingyue Cui ,
  • Bowen Wang ,
  • Chunmei Hu ,
  • Yingying Zheng ,
  • Jing Li ,
  • Xuetao Xu ,
  • Zhen Wang ,
  • Shaohua Wang
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  • a School of Pharmacy, Lanzhou University, Lanzhou 730000
    b School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020
* Corresponding authors. E-mail: ;
E-mail:

Received date: 2020-10-30

  Revised date: 2020-12-10

  Online published: 2020-12-24

Supported by

National Natural Science Foundation of China(21472077); National Natural Science Foundation of China(21772071); Department of Education of Guangdong Province(2017KTSCX185); Department of Education of Guangdong Province(2017KSYS010); Department of Education of Guangdong Province(2019KZDXM035)

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摘要

利用环丙烯酮同时具有亲核性、亲电性以及易发生开环反应的特点, 实现了三乙胺促进的环丙烯酮和α-卤代异羟肟酸酯类化合物的[3+3]环加成反应, 快速构筑了6H-1,3-噁嗪-6-酮骨架, 为噁嗪酮类化合物的合成提供了新的思路. 该反应在无金属和温和条件下显示出良好的收率和官能团耐受性, 同时适合克级规模制备.

关键词： 环丙烯酮; α-卤代异羟肟酸酯; 环化反应; 噁嗪酮

本文引用格式

刘思展 , 崔明月 , 王博文 , 胡春梅 , 郑莹莹 , 李晶 , 徐学涛 , 王震 , 王少华 . 三乙胺促进的环丙烯酮和α-卤代异羟肟酸酯的环化反应合成多取代6H-1,3-噁嗪-6-酮[J]. 有机化学, 2021 , 41(4) : 1622 -1630 . DOI: 10.6023/cjoc202010041

Abstract

A triethyl amine-promoted cyclization reaction between cyclopropenone and α-halohydroxamate has been developed to give an alternative synthetic strategy for the construction of 6H-1,3-oxazin-6-one skeleton. The reaction shows good yield and functional group tolerance under metal-free and mild conditions, and it is suitable for gram-scale preparation.

Key words： cyclopropenone; α-halogenated hydroxamate; cyclization reaction; oxazinone

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