CARBOXYL-MEDIATED PICTET-SPENGLER REACTION - DIRECT SYNTHESIS OF 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES FROM TRYPTAMINE-2-CARBOXYLIC ACIDS

被引：40
|
作者：
NARAYANAN, K [1 ]
SCHINDLER, L [1 ]
COOK, JM [1 ]
机构：
[1] UNIV WISCONSIN,DEPT CHEM,MILWAUKEE,WI 53201
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 01期
关键词：
D O I：
10.1021/jo00001a066
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Pictet-Spengler condensation of various tryptamine-2-carboxylic acids 9a-f with carbonyl compounds in benzene/dioxane/trifluoroacetic acid (Table I) with simultaneous loss of carbon dioxide afforded directly the corresponding 1,2,3,4-tetrahydro-beta-carbolines 14a-j in good to excellent yields. This reaction greatly enhances the use of the Abramovitch-Shapiro method for the synthesis of highly oxygenated ring A substituted 1,2,3,4-tetrahydro-beta-carbolines (THBC). The lactams 14f,g and 14h are key intermediates for the synthesis of ring A substituted 1-methoxycanthin-6-one analogues.
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页码：359 / 365
页数：7
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