Stereoselective synthesis of 1,3,4-substituted tetrahydro-beta-carbolines from indoles based on selective transformations

被引：18

作者：

Ezquerra, J

Pedregal, C

Lamas, C

Pastor, A

Alvarez, P

Vaquero, JJ

机构：

[1] CTR INVEST LILLY, VALDEOLMOS 28130, MADRID, SPAIN

[2] UNIV ALCALA DE HENARES, DEPT QUIM ORGAN, E-28871 ALCALA DE HENARES, MADRID, SPAIN

来源：

TETRAHEDRON | 1997年 / 53卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(97)00489-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1, 3, 4-Substituted tetrahydro beta-carbolines 4 have been prepared from indoles 6 by two selective transformations: first, nucleophilic aziridine ring opening with a lower order indolyl magnesium cuprate obtaining the alpha, beta-substituted tryptamines 5 and secondly, a ''Pictet-Spengler-like'' reaction between azalactones 12 and tryptamines 5, Under the acidic reaction conditions used, the thermodynamically favoured tetrahydro beta-carbolines 4 are obtained due to the conformational restrictions imposed by the tryptamine substituents. (C) 1997 Elsevier Science Ltd.

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页码：8237 / 8248

页数：12

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