Merrifield树脂负载的固相法合成1-氨基-2,4-咪唑二酮

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.

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

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.