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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (03): 295-298. 上一篇    下一篇

研究论文

2-氨基噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物的合成

胡扬根1, b，吕茂云1，宋鹤丽1，丁明武*,1   

  1. (1 华中师范大学化学学院 教育部农药与化学生物学重点实验室 武汉 430079)
    (2 郧阳医学院医用化学教研室 十堰 442000)
  • 收稿日期:2004-05-19 修回日期:2004-09-13 发布日期:2005-02-28
  • 通讯作者: 丁明武

Synthesis of 2-Amino-thieno[2,3-d]pyrimidin-4(3H)-ones

HU Yang-Gen1,2,LU Mao-Yun1,SONG He-Li1,DING Ming-Wu*,1   

  1. (1 Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry,
    Central China Normal University, Wuhan 430079)
    (2 Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000)
  • Received:2004-05-19 Revised:2004-09-13 Published:2005-02-28
  • Contact: DING Ming-Wu

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丁醛(1)、氰乙酸乙酯、硫磺在三乙胺作用下制得2-氨基-4-乙基噻吩-3-羧酸乙酯(2), 2再与三苯基膦、六氯乙烷及三乙胺反应, 以84%的产率得到膦亚胺3. 应用膦亚胺3与芳基异氰酸酯的氮杂Wittig反应, 生成的碳二亚胺4, 再与仲胺作用得到中间体5, 而后在醇钠的催化下关环制得2-二烷氨基噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物6, 产率为58%～82%.

关键词: 噻吩并[2,3-d]嘧啶-4(3H)-酮, 氮杂Wittig反应, 合成, 碳二亚胺

Ethyl 2-amino-4-ethylthiophene-3-carboxylate (2), obtained from reaction of butyraldehyde (1), ethyl cyanoacetate, sulfur and triethylamine, reacted with triphenylphosphine, hexachloroethane and triethylamine to give iminophosphorane 3 in 84% yield. Further aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates gave the carbodiimides 4, which were reacted with secondary amines to give 2-dialkylamino-thieno[2,3-d]pyrimidin-4(3H)-ones 6 in the presence of catalytic amounts of EtO－Na＋in 58%～82% yields.

Key words: thieno[2,3-d]pyrimidin-4(3H)-one, carbodiimide, synthesis, aza-Wittig reaction