松果腺素的合成

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

以四氢呋喃、4 甲氧基苯胺为主要原料 ,经五步合成了松果腺素。四氢呋喃和氯化氢气体在 1 0 5℃下反应 0 5h ,得到 4 氯丁醇 (Ⅰ) ,产率为 6 8 6 % ;(Ⅰ)用氯铬酸吡啶盐氧化得 4 氯丁醛 (Ⅱ) ,产率为6 0 7% ;4 甲氧基苯胺经重氮化和还原反应得 4 甲氧基苯肼 (Ⅲ) ,产率为 6 0 9% ;(Ⅱ) +(Ⅲ)经环化得 5 甲氧基色胺 (Ⅳ) ,产率为 47 6 % ;(Ⅳ)经乙酰化得松果腺素 (Ⅴ) ,产率为 83 5 %。

The title compound was prepared by a five step reaction route with tetrahydrofuran and 4 anisidine as the main reactants.Tetrahydrofuran reacted with gaseous hydrogen chloride at 105 ℃ for 0 5 h to give 68.6% 4 chloro butylalcohol (Ⅰ).Ⅰ was oxidized by pyridine salt of chlorochromic acid to give 60.7% 4 chlorobutyraldehyde (Ⅱ).From 4 anisidine through diazotization and reduction reactions,4 methoxyphenylhydrazine (Ⅲ) was obtained in 60 9% yield.Ⅱ condensed with Ⅲ to give 47.6% 5 methoxytryptamine (Ⅳ).Finally Ⅳ was acetylated to give the title compound (Ⅴ) in 83 5% yield.