STRUCTURE AND SPECTRAL PROPERTIES OF BETA-CARBOLINES .4. SYNTHESIS OF THE NEW RING-SYSTEM - 9,10,15,15B-TETRAHYDROINDOLO[1',2'-4,3]PYRAZINO[2,1-A]CARBOLIN-7(6H)-ONE

被引：8
|
作者：
MISZTAL, S [1 ]
BIELECKA, Z [1 ]
MOKROSZ, JL [1 ]
机构：
[1] POLISH ACAD SCI,INST PHARMACOL,DEPT ORGAN CHEM,12 SMETNA ST,PL-31343 KRAKOW,POLAND
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 08期
关键词：
D O I：
10.1039/p19910001871
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1-Indol-2-yl-1,2,3,4-tetrahydro-beta-carboline and its 5-methoxy derivative were synthesized by the Pictet-Spengler reaction between tryptamine or 5-methoxytryptamine and indole-2-carbaldehyde, with a high yield. A step-by-step oxidation of the indolyl carbolines led to formation of the appropriate dihydrocarboline derivatives and two analogues of neoeudistomine, the fully unsaturated carbolines. Condensation of the indolyltetrahydrocarbolines with bromoacetyl chloride yielded the appropriate 2-substituted derivatives, which were cyclized to yield the new ring system compounds 9,10,15,15b-tetrahydroindolo[1',2':4,3]pyrazino[2,1 -a]carbolin-77 (6H)-ones, the structures of which were determined by using a high-resolution H-1 NMR technique.
引用
收藏
页码：1871 / 1874
页数：4
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