Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (02): 265-268. Previous Articles     Next Articles

Reports

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

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