有机化学 ›› 2017, Vol. 37 ›› Issue (10): 2711-2716.DOI: 10.6023/cjoc201705021 上一篇    下一篇

研究论文

无催化剂一锅法合成4-取代喹唑啉

李灵杰, 张敬, 唐渝, 许开天, 张渊明   

  1. 暨南大学化学与材料学院化学系 广州 510632
  • 收稿日期:2017-05-15 修回日期:2017-06-05 出版日期:2017-10-25 发布日期:2017-06-16
  • 通讯作者: 唐渝, 张渊明 E-mail:tytang@jnu.edu.cn;tzhangym@jnu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21274083)资助项目.

Catalyst-Free One-Pot Synthesis of 4-Substituted Quinazolines

Li Lingjie, Zhang Jing, Tang Yu, Xu Kaitian, Zhang Yuanming   

  1. Department of Chemistry, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632
  • Received:2017-05-15 Revised:2017-06-05 Online:2017-10-25 Published:2017-06-16
  • Contact: 10.6023/cjoc201705021 E-mail:tytang@jnu.edu.cn;tzhangym@jnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21274083).

报道了一种无需催化剂一锅法制备喹唑啉类化合物的新方法,制备的15个喹唑啉化合物中,其中有3个新化合物,收率在37%~95%.探讨了溴代烃的电子效应和空间位阻效应对反应的影响,提出了可能涉及重复亲核加成、消除生成喹唑啉的新机理,并因此而扩展到用酸酐代替N,N-二甲基甲酰胺(DMF)的反应.

关键词: 喹唑啉, 一锅法, 无催化剂, 格氏试剂, 合成

A novel and catalyst-free one-pot method for the preparation of quinazoline compounds has been reported. Of the prepared 15 quinazoline compounds, three are new compounds. Their yields are among 37%~95%. The effects of electron effect and steric hindrance on the reaction were discussed. A plausible novel mechanism concerning repeating nucleophilic addition and elimination to give quinazoline has been proposed. By this mechanism, the reaction could be applied to acid anhydride instead of N,N-dimethylformamide (DMF).

Key words: quinazoline, one-pot, catalyst-free, Grignard reagent, synthesis