有机化学 ›› 2014, Vol. 34 ›› Issue (6): 1177-1182.DOI: 10.6023/cjoc201308020 上一篇    下一篇

研究论文

有机碱催化的H-亚磷酸酯与靛红及其衍生物的phospho-Aldol-Brook重排串联反应

方魏a, 刘国桂b, 黄晓飞b, 贾俊a, 王兴旺b   

  1. a. 苏州大学分析测试中心 苏州 215123;
    b. 苏州大学材料与化学化工学部 苏州 215123
  • 收稿日期:2013-08-16 修回日期:2013-12-18 出版日期:2014-06-25 发布日期:2014-02-12
  • 通讯作者: 贾俊 E-mail:jiajun@suda.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21272166)和江苏省属高校自然科学研究(No. 13KJA150004)资助项目.

Organic Base Catalyzed Cascade Phospho-Aldol-Brook Rearrangement Reaction of Isatins with H-phosphonates

Fang Weia, Liu Guoguib, Huang Xiaofeib, Jia Juna, Wang Xingwangb   

  1. a. Analysis and Testing Center, Soochow University, Suzhou 215123;
    b. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123
  • Received:2013-08-16 Revised:2013-12-18 Online:2014-06-25 Published:2014-02-12
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272166) and the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 13KJA150004).

在温和的反应条件下,以1,1,3,3-四甲基胍(TMG)或1,8-二氮杂二环[5.4.0]十一碳-7-烯(DBU)有机碱作为催化剂,催化H-亚磷酸酯与靛红的phospho-Aldol-Brook重排串联反应,高效、高产率合成了两个系列α-羟吲哚基-磷酸酯类化合物.

关键词: α-羟吲哚基-磷酸酯, 靛红, H-亚磷酸酯, Brook重排, 串联反应

A cascade phospho-aldol-Brook rearrangement reaction of isatins with H-phosphonates was reported by the use of the organic base, such as 1,1,3,3-tetramethylguanidine (TMG) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), as an organocatalyst. Two series of 2-oxoindolin-3-yl phosphates were obtained in good to excellent yields under mild reaction conditions.

Key words: α-oxindole-phosphonates, isatins, H-phosphonates, Brook rearrangement, cascade reaction