Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (7): 1369-1375.DOI: 10.6023/cjoc201402005 Previous Articles     Next Articles

ARTICLE

铁催化2-烯基氮杂芳烃的绿色合成

刘森生a, 姜坤a, 皮单违a, 周海峰a,b, Yasuhiro Uozumib, 邹坤a   

  1. a 三峡大学生物与制药学院 天然产物研究与利用湖北省重点实验室 宜昌 443002;
    b 分子科学研究所 冈崎市 日本 444-8787
  • 收稿日期:2014-02-05 修回日期:2014-03-22 发布日期:2014-04-02
  • 通讯作者: 周海峰 E-mail:haifeng-zhou@hotmail.com
  • 基金资助:

    国家自然科学青年基金(No.21202092)和三峡大学人才科研启动基金(No.KJ2012B080)资助项目

Iron-Catalyzed Green Synthesis of 2-Alkenylazaarenes

Liu Senshenga, Jiang Kuna, Pi Danweia, Zhou Haifenga,b, Uozumi Yasuhirob, Zou Kuna   

  1. a Hubei Key Laboratory of Natural Products Research & Development, College of Biological & Pharmaceutical Sciences, China Three Gorges University, Yichang 443002;
    b Institute for Molecular Science, Okazaki, Japan 444-8787
  • Received:2014-02-05 Revised:2014-03-22 Published:2014-04-02
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21202092) and the Startup Foundation from China Three Gorges University (No. KJ2012B080).

A straightforward and selective synthesis of bioactive trans-2-alkenylazaarenes has been achieved via cheap and nontoxic iron(II) acetate catalyzed addition and dehydration reactions of 2-methylazaarenes and aromatic aldehydes in the presence of catalytic amount of trifluoroacetic acid with water as the only byproduct. The low catalyst loading, convenience, good yield, high selectivity, as well as the broad substrate scope make this protocol very practical. The practical potential was also demonstrated by gram-scale synthesis of (E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde (3v), an intermediate of Singulair.

Key words: alkenylation, nitrogen heterocycles, C-H activation, green chemistry