METAL TRIFLUOROPYRUVATE IN THE PICTET-SPENGLER REACTION

被引:0
|
作者
GOLUBEV, AS
CHKANIKOV, ND
ANTIPIN, MY
STRUCHKOV, YT
KOLOMIETS, AF
FOKIN, AV
机构
关键词
METHYL TRIFLUOROPYRUVATE; 2-(3,4-DIMETHOXYPHENYL)ETHYLAMINE; TRYPTAMINE; (D; L)-TRYPTOPHAN; PICTET-SPENGLER REACTION; 1,2,3,4-TETRAHYDROISOQUINOLINES; 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES;
D O I
10.1007/BF00864340
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Condensation of methyl trifluoropyruvate with 2-(3,4-dimethoxyphenyl)ethylamine, tryptamine, and (D, L)-tryptophan yielded 1-methoxycarbonyl-1-trifluoromethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, 1-methoxycarbonyl-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, and Z-1-methoxycarbonyl-1-trifluoromethyl-3-carboxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, respectively. The Z configuration of the latter was determined by x-ray structural analysis.
引用
收藏
页码:1425 / 1429
页数:5
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