一种简便的松果腺素的合成方法

以邻苯二甲酰亚胺钾、１，３二溴丙烷、对甲氧基苯胺为主要原料，经５步化学反应合成了松果腺素：邻苯二甲酰亚胺钾和１，３－二溴丙烷在１５５～１６０℃下反应６ｈ，得到Ｎ－（３－溴丙基），邻苯二甲酸亚胺（Ⅱ），产率７７％；Ⅱ在乙醇钠存在下和乙酰乙酸乙酯作用得到２－乙酸基－５－邻苯二甲酰亚氨基戊酸乙酯（Ⅲ），产率７２％；Ⅲ与对甲氧基苯胺重氮盐偶联后发生环化作用，生成Ｔ２－羧乙基－３－（２－邻苯二甲酰亚氨乙基）－５－甲氧基吲哚（Ⅳ），产率７４％；Ⅳ经碱皂化、水解、脱羧反萃取纯化，得到５．甲氧基色胺（Ｖ），产率６６％；Ｖ经乙酸化后得到松果腺素（Ⅵ），产率８２％。

A Convenient Synthesis of N-Acetyl-5-methoxytryptamine(Melatonin)

The tide compound was prepared by a five-step reaction route with K-phthalimide, 1, 3-dibromo-propane and 4-anisidine as the main reactants. After K-phthalimide reaction with l, 3-dibromo-propane at 155 ~ 160℃ for 6h to give N(3 - bromopropyl ) phthalimide (Ⅱ ) in 77 % yield, Ⅱ was condensed with Et acetacetate in the presence of NaOEt, lead lug to ethyl-5 - Phthalimido- pentanoate (Ⅲ ) in 7 2 % yield. Ⅲ was Cyclocondensed with diazotized 4- anisidine to produce carboxyethtyl-5- (2- phthalimidoethyl ) -5 -methoxy- indole (Ⅳ ) in 74 % yield, which after sapohified with NaOH, hydrolyzed, decarboxylated in the solution of H_2SO_4, and purified with strip-extraction gave 5-methoxytryptamine (V ) in 66% yield. V was acetylated to give the tide compound(Ⅵ) in 82% yield.