有机化学 ›› 2017, Vol. 37 ›› Issue (5): 1252-1257.DOI: 10.6023/cjoc201701024 上一篇    下一篇

研究论文

CeCl3·7H2O催化Groebke-Blackburn-Bienayme反应简便合成咪唑稠杂环化合物(英文)

张钊瑞, 徐良, 唐汉秦, 吴伯鑫, 冯迪, 郭长彬   

  1. 首都师范大学化学系 北京 100048
  • 收稿日期:2017-01-10 修回日期:2017-02-12 出版日期:2017-05-25 发布日期:2017-02-20
  • 通讯作者: 郭长彬 E-mail:guocb@cnu.edu.cn
  • 基金资助:

    国家自然科学基金(No.30873140)、北京市优秀人才培养(No.20071D0501600227)、北京市教委科技发展(No.KM201010028011)资助项目.

Convenient Synthesis of Imidazo-Fused Heterocycles via CeCl3·7H2O Catalyzed Groebke-Blackburn-Bienayme Reaction

Zhang Zhaorui, Xu Liang, Tang Hanqin, Wu Boxin, Feng Di, Guo Changbin   

  1. Department of Chemistry, Capital Normal University, Beijing 100048
  • Received:2017-01-10 Revised:2017-02-12 Online:2017-05-25 Published:2017-02-20
  • Contact: 10.6023/cjoc201701024 E-mail:guocb@cnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 30873140), the Program for Excellent Talents of Beijing City (No. 20071D0501600227) and the Beijing Municipal Commission of Education (No. KM201010028011).

发展了由CeCl3·7H2O催化“一锅法”Groebke-Blackburn-Bienayme(GBB)反应合成咪唑稠杂环化合物的一种简单、高效和环境友好的合成方法.该反应以醛、氨基吖嗪、异腈三组分为原料,CeCl3·7H2O为催化剂,乙醇作为反应介质、60℃反应温度下可高收率合成相应咪唑稠杂环化合物.该方法具有底物范围广,反应时间短,纯化方法简单的优势.通过CeCl3·7H2O和高效催化剂LaCl3·7H2O的对比研究发现,CeCl3·7H2O具有同样高的催化效率,为咪唑稠杂环化合物的合成提供了一种新的便利方法.

关键词: Groebke-Blackburn-Bienayme反应, 咪唑稠杂环, CeCl3·H2O, LaCl3·H2O

A simple, efficient and eco-friendly “one-pot” method for the convenient synthesis of imidazo-fused heterocycles has been developed. The reaction was catalyzed by CeCl3·7H2O in ethanol under 60 ℃ via Groebke-Blackburn-Bienayme (GBB) reaction of aldehydes, aminoazines and isocyanides. This method has many advantages of a wide range of substrates, short reaction time and easy purification. In addition, we conducted a comparative study of LaCl3·7H2O with CeCl3·7H2O on their catalytic effect under the same reaction conditions, and found that CeCl3·7H2O was comparable to LaCl3·7H2O as catalyst in GBB reaction.

Key words: Groebke-Blackburn-Bienayme reaction, imidazo-fused heterocycles, CeCl3·H2O, LaCl3·H2O