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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (02): 207-211. 上一篇    下一篇

研究论文

6-溴-N-芳基噻吩[2,3-d]并嘧啶-4-胺类化合物的合成新方法

詹冬梅1，李思远1，赵红莉1，蓝闽波*,1,2   

  1. (1上海市功能性材料化学重点实验室 华东理工大学分析测试中心 上海 200237)
    (2华东理工大学生物反应器工程国家重点实验室 上海 200237)
  • 收稿日期:2010-07-09 修回日期:2010-09-14 发布日期:2010-09-27
  • 通讯作者: 蓝闽波 E-mail:minbolan@ecust.edu.cn

A Novel Synthetic Method for 6-Bromo-N-aryl-thieno[2,3-d]- pyrimidin-4-amines

Zhan Dongmei1 Li Siyuan1 Zhao Hongli1 Lan Minbo*,1,2   

  1. (1 Shanghai Key Laboratory of Functional Materials Chemistry, and Research Centre of Analysis and Test, East China University of Science and Technology, Shanghai 200237)
    (2 State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237)
  • Received:2010-07-09 Revised:2010-09-14 Published:2010-09-27

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研究了6-溴-N-[3-氯-4-(3-氟苄氧基)苯基]噻吩[2,3-d]并嘧啶-4-胺的合成新方法. 以相对廉价的2,5-二羟基-1,4-二噻烷和丙二腈为原料, 依次通过Gewald反应、芳环溴代、缩合、环合以及Dimroth重排四步反应得到目标产物6-溴-N-[3-氯-4-(3-氟苄氧基)苯基]噻吩[2,3-d]并嘧啶-4-胺, 总产率为56.9%. 用1H NMR, IR, MS和HRMS对产物进行了结构表征. 并应用该方法, 合成了一系列的6-溴-N-芳基噻吩[2,3-d]并嘧啶-4-胺类化合物. 研究表明该方法具有原料易得、操作简便、收率较高, 且产物容易分离纯化等优点.

关键词: 噻吩[2,3-d]并嘧啶, Dimroth重排, 合成方法, 机理

In this paper, a novel synthetic method for 6-bromo-N-[3-chloro-4-(3-fluorobenzyloxy)phenyl]- thieno[2,3-d]pyrimidin-4-amine was reported, which began from cheap 2,5-dihydroxy-1,4-dithiane and malononitrile, following Gewald reaction, aromatic ring bromonation, condensation, cyclization and then Dimroth rearrangement reaction. The over yield was 56.9%. The structures of synthesized compounds were determined by 1H NMR, IR, MS and HRMS techniques. Employing the same synthetic method, a series of 6-bromo-N-arylthieno[2,3-d]pyrimidin-4-amine derivatives were synthesized. The results showed that the advantages of this method were simply available starting meterials, easily conducted procedure, relatively high yield, and easily purification of the products.

Key words: thieno[2,3-d]pyrimidines, Dimroth rearrangement, synthetic method, mechanism