N—乙酰基—5—甲氧基色胺的合成

Synthesis of N Acetyl 5 Methoxytryptamine

  • 摘要: 目的 研究并改进松果体素的合成。方法 以丙烯腈为原料与丙二酸乙酯经Michael反应,所得产物用Raney Ni粉末电极在甲醇介质中以2.5A/dm^2的电流密度电催化还原,得到3-羧酸乙酯-2-哌啶酮,再经过重氮化反应,Fischer吲哚化反应,咔啉的开环和脱羧,乙酰化共6步反应,制得N-乙酰基-5-甲氧基色胺。结果与结论 电催化还原2-氰基乙基丙二酸二乙酯,获得90%的收率,常压下把腈基还原为

     

    Abstract: Aim To study and modify the synthesis method of melatonine. Methods Michael reaction was carried out with diethyl malonate and acrylonitrile used as starting materials. Then above reaction product was electro catalytically reduced to 2 oxopiperidine 3 carboxylate at 2 5 A/dm 2 with Raney Ni used as catalytically active powder electrode in the presence of methanol. Next,after diazotisation, Fischer indolization,ring opening and decarboxylation of carboline, and carbonylation reactions, the aim product N acetyl 5 methoxytryptamine was obtained. Results and Conclusion The 90% yield is obtained when 2 cyanoethyl diethyl malonate is reduced with the electrocatalytic method. Hydrogenating of high pressure condition is avoided in the electrocatalytic reduction process of cyano group to amino group. The over all yield of melatonine by above method is 25%.

     

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