A new synthesis of rizatriptan based on radical cyclization

被引：0

作者：

Radl, Stanislav ^{[1
]}

Klecan, Ondrej ^{[1
]}

Klvana, Robert ^{[1
]}

Havlicek, Jaroslav ^{[1
]}

机构：

[1] Zentiva, Prague 10237 10, Czech Republic

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2008年 / 73卷 / 01期

关键词：

rizatriptan; triptans; migraine treatment drugs; serotonin agonists; radical cyclizations; Indoles; Mannich reaction;

D O I：

10.1135/cccc20080116

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new methodology useful for preparation of indole derivatives bearing a 2-(dialkylamino)-ethyl substituent at the 3-position has been developed. Application of this methodology to the synthesis of N, N-dimethyl-2-{5-[(1H-1,2,4-triazol-1-yl)methyl]-1H-indol-3-yl}ethan-1- amine ( rizatriptan; 3) is described. The key reaction step is based on the radical cyclization of N-[4-(dimethylamino)but-2-yn-1-yl]-N-{2-iodo-4-[(1H-1,2,4-triazol-1-yl) methyl] phenyl}acetamide ( 21), easily available by the Mannich reaction, and subsequent isomerization of the primarily formed methylidene derivative 22.

引用

页码：116 / 126

页数：11

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