高等学校化学学报 ›› 1991, Vol. 12 ›› Issue (3): 332.

• 论文 • 上一篇    下一篇

2-(三甲氧基苯基)色胺盐酸盐的合成

邱玉珠, 杭超, 张正, 胡宏纹   

  1. 南京大学化学系, 210008
  • 收稿日期:1989-09-15 出版日期:1991-03-24 发布日期:1991-03-24
  • 通讯作者: 邱玉珠

Synthesis of 2-(Trimcthoxyphenyl) Tryptamines Hydrochloride

Qiu Yu-zhu, Hang Chao, Zhang Zheng, Hu Hong-wen   

  1. Department of Chemistry, Nanjing University, Nanjing, 210008
  • Received:1989-09-15 Online:1991-03-24 Published:1991-03-24

摘要: 2,3,4-及3,4,5-三甲氧基苯乙酮苯腙在多聚磷酸存在下进行Fischer反应,可生成相应的吲哚(1a,1b),但2,4,6-三甲氧基苯乙酮苯腙必须用无水氯化锌催化环化才能得到相应的吲哚(1c)。1a、1b、1c经Vilsmier反应生成相应的吲哚-3-醛(2a,2b,2c);经与硝基甲烷缩合得到相应的2-(三甲氧基苯基)-3-(2-硝基乙烯基)吲哚(3a,3b,3c);3a及3b用LiAlH4还原即可制备成相应的色胺盐酸盐(4a和4b),3b还被制成苦味酸盐(4b)。

关键词: 吲哚, 色胺, 还原

Abstract: In the presence of PPA, 2-( 2, 3, 4-trimethoxyphenyl) indole ( 1a) and 2-(3,4,5-trimethoxyphenyl) indole (1b) were prepared by the Fischer synthesis from the corresponding trimethoxyacetophenone phenylhydrazones. 2-(2, 4, 6-Trimethoxyphenyl)indole(1c) was prepared by treating 2, 4,6-trimethoxy acetophenone phenylhydrazone with anhydrous zinc chloride. 1a, 1b, 1cwere converted to the 3-formyl derivatives 2a, 2b, 2Cunder Vilsmier reaction conditions, respectively, and 2a, 2b, 2Cwere condensed with nitromethane to give the corresponding 3-(2-nitroethenyl)in-doles 3a, 3band 3C. Reduction of 3aor 3bwith LiAlH, gaves the corresponding tryptamines 4aand 4b, respectively.

Key words: Indole, Tryptamine, Reduction

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