有机化学 ›› 2019, Vol. 39 ›› Issue (1): 129-136.DOI: 10.6023/cjoc201809014 上一篇    下一篇

所属专题: 庆祝陈庆云院士九十华诞

研究论文

铁卟啉催化酮和二甲亚砜以及醋酸铵的环化反应:吡啶的一步合成

刘玉峰, 曹重仲, 苏淼东, 李慧, 符美强, 刘强, 罗伟平, 郭灿城   

  1. 湖南大学化学化工学院 教育部先进催化工程研究中心 长沙 410082
  • 收稿日期:2018-09-07 修回日期:2018-11-29 发布日期:2018-12-05
  • 通讯作者: 郭灿城 E-mail:ccguo@hnu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21572049)资助项目.

Iron(Ⅲ) Porphyrin Catalyzed Cyclization of Ketones with Dimethyl Sulfoxide and Ammonium Acetate: One-Pot Synthesis of Pyridines

Liu Yufeng, Cao Zhongzhong, Su Miaodong, Li Hui, Fu Meiqiang, Liu Qiang, Luo Weiping, Guo Cancheng   

  1. Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2018-09-07 Revised:2018-11-29 Published:2018-12-05
  • Contact: 10.6023/cjoc201809014 E-mail:ccguo@hnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundations of China (No. 21572049).

发展了一种在铁卟啉催化下酮和二甲亚砜(DMSO)以及醋酸铵的环化反应,该反应利用DMSO作为碳源来合成不对称和对称的吡啶化合物,多种酮能够很好地和DMSO反应产生吡啶化合物,产率在30%到85%之间.该方法利用非贵金属和简单酮类化合物来合成吡啶,条件温和,操作简单.在初步的控制实验基础上,提出了该反应可能的机理.

关键词: 吡啶, 铁卟啉, 二甲亚砜,

An iron(Ⅲ)-porphyrin-catalyzed cyclization of ketones with dimethyl sulfoxide (DMSO) and ammonium acetate for the synthesis of unsymmetrical and symmetrical pyridines by employing DMSO as C4 or C6 source has been developed. Various aryl ketone derivatives react readily with DMSO, producing the pyridines in yields of 30%~85%. This method uses non-noble metals and proceeds under mild reaction conditions with operational simplicity, which thus allows the expedient assembly of pyridines from readily available ketones. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.

Key words: pyridine, iron (III) porphyrin, dimethyl sulfoxide, ketone