SYNTHESIS OF FUNCTIONALIZED 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES FROM ENAMINO KETONES

被引：0

作者：

TIETZE, LF

WICHMANN, J

机构：

来源：

LIEBIGS ANNALEN DER CHEMIE | 1992年 / 10期

关键词：

ENAMINO KETONES; PICTET-SPENGLER REACTIONS; BETA-CARBOLINES, 1,2,3,4-TETRAHYDRO-; INDOLES; 2-SUBSTITUTED;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of tryptamine (1) with 2 and 3 gives the enamino ketones 4a and 5, resp., which on treatment with trifluoroacetic acid lead to the 2-substituted indoles 8 and 9, respectively. Acylation of 4a followed by reaction with trifluoroacetic acid or a Lewis acid affords the 1,2,3,4-tetrahydro-beta-carbolines 7b - e in excellent yields. Treatment of 8 with anhydrides like (CF3CO)2O also yields the 1,2,3,4-tetrahydro-beta-carboline 7f. The trichloromethylcarbonyl group in 7 can easily be converted into dn ester moiety by reaction with an alcohol in the presence of K2CO3.

引用

页码：1063 / 1067

页数：5

共 36 条

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