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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (02): 265-268. 上一篇    下一篇

研究简报

Merrifield树脂负载的固相法合成1-氨基-2,4-咪唑二酮

裴 文*; 陶金海; 孙 莉; 孙孟展   

  1. (浙江工业大学化学工程与材料学院 杭州 310014)
  • 收稿日期:2007-09-09 修回日期:2007-12-25 发布日期:2009-02-20
  • 通讯作者: 裴 文

Merrifield Resin Supported Solid Phase Synthesis of 1-Amino-2,4-imidazolidinedione

Pei, Wen*; Tao, Jinhai ; Sun, Li ; Sun, Mengzhan   

  1. (College of Chemical Engineering and Materials, Zhejiang University of Technology, Hangzhou 310014)
  • Received:2007-09-09 Revised:2007-12-25 Published:2009-02-20
  • Contact: Pei, Wen

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被引次数

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设计了两条新的固相有机合成路线合成了1-氨基-2,4-咪唑二酮化合物4. 一条是由Merrifield树脂负载的羟基苯甲醛1a～1c和氨基脲反应得到缩氨基脲树脂2a～2c, 再在乙醇钠存在下和氯乙酸乙酯成环, 经盐酸切割得到1-氨基-2,4-咪唑二酮; 另一条是将Merrifield树脂用二甲基亚砜氧化氯甲基末端醛化后, 与氨基脲反应得到负载的缩氨基脲6, 经环化、切割得到目标产物4. 这两种方法中用1 mol/L的盐酸代替三氟乙酸作为切割剂, 产物单一、操作简便、可定量反应, 是合成1-氨基-2,4-咪唑二酮化合物的新方法.

关键词: 1-氨基-2,4-咪唑二酮, 固相有机合成, Merrifield树脂

The two novel ways of solid phase organic synthesis for preparing 1-amino-2,4-imidazolidinedione (4) were developed: (1) Merrifield resin-supported hydroxy substituted benzaldehydes (1a～1c) were reacted with semicarbazide compound to give resin-supported semicarbazone (2a～2c), followed cyclization with ethyl monochloroacetate in the presence of sodium ethoxide, clove with hydrochloric acid solution to give 1-amino-2,4-imidazolidinedione. (2) Merrifield resin-bound aldehyde prepared from Merrifield resin oxidized with DMSO was reacted with semicarbazide compound to givie resin-supported semicarbazone 6, then cyclized and clove to give product 4. The cleavage way has advantage of obtaining single and quantita-tive product and simplifying purified procedure using 1 mol/L hydrochloric acid solution instead of trifluoroacetic acid solution.

Key words: solid-phase organic synthesis, Merrifield resin, 1-amino-2,4-imidazolidinedione