有机化学 ›› 2017, Vol. 37 ›› Issue (1): 166-175.DOI: 10.6023/cjoc201607002 上一篇    下一篇

研究论文

酰胺类杂环烯酮缩胺的合成

罗大云, 崔时胜, 胡兴梅, 林军, 严胜骄   

  1. 云南大学化学科学与工程学院 教育部自然资源药物化学重点实验室 昆明 650091
  • 收稿日期:2016-07-02 修回日期:2016-08-25 出版日期:2017-01-25 发布日期:2016-09-08
  • 通讯作者: 林军, 严胜骄 E-mail:linjun@ynu.edu.cn;yansj@ynu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21362042,U1202221,21662042)、云南省后备人才(No. 2012HB001)、云南大学青年英才计划(No. XT412003)资助项目.

Synthesis of Amide Class Heterocyclic Ketene Aminals

Luo Dayun, Cui Shisheng, Hu Xingmei, Lin Jun, Yan Shengjiao   

  1. Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091
  • Received:2016-07-02 Revised:2016-08-25 Online:2017-01-25 Published:2016-09-08
  • Supported by:

    Project supported by the National Natural Science Foundation of China(Nos. 21362042, U1202221, 21662042), the Talent Found in Yunnan Province(No. 2012HB001), and the Excellent Young Talents, Yunnan University(No. XT412003).

建立了以杂环烯酮缩胺(HKAs)为原料,用芳基异氰酸酯为酰化剂,实现杂环烯酮缩胺选择性酰化.通过该区域选择性反应简洁、快速地合成了一系具有潜在药理活性的酰胺类杂环烯酮缩胺化合物的方法.该方法以六元或七元环杂环烯酮缩胺1~2与芳基异氰酸酯4在1,4-二氧六环溶剂中室温下合成杂环烯酮缩胺α-碳选择性酰基化产物5~6,产率90%~98%;而五元环杂环烯酮缩胺3与芳基异氰酸酯4在1,4-二氧六环溶剂中碳酸铯催化室温下合成杂环烯酮缩胺选择性氮酰基化产物7,产率78%~93%.

关键词: 杂环烯酮缩胺, 异氰酸酯, 区域选择性, 酰化反应

In this paper,a concise protocol for synthesis of possess potential pharmacological active amide class heterocyclic ketene aminals(HKAs) has been developed,which based on the six or seven-membered HKAs 1~2,using aryl isocyanate 4 as acylation agent.The regioselective acylation reaction of HKAs in 1,4-dioxane at room temperature gave compounds 5~6 with 90%~98% yields.However,the five-membered HKAs 3 and aryl isocyanate 4 reacted in 1,4-dioxane catalyzed by Cs2CO3 at room temperature to obtain compounds 7 in 78%~93% yields.

Key words: heterocyclic ketene aminals, isocyanate, regioselective, acylation reaction