Synthesis of indoles: Efficient functionalisation of the 7-position

被引：24

作者：

Charrier, Nicolas ^{[1
]}

Demont, Emmanuel ^{[1
]}

Dunsdon, Rachel ^{[1
]}

Maile, Graham ^{[1
]}

Naylor, Alan ^{[1
]}

O'Brien, Alistair ^{[1
]}

Redshaw, Sally ^{[1
]}

Theobald, Pam ^{[1
]}

Vesey, David ^{[1
]}

Walter, Daryl ^{[1
]}

机构：

[1] GlaxoSmithKline Inc, Neurol & Gastrointestinal Ctr Excellence Drug Dis, Harlow CM19 5AW, Essex, England

来源：

SYNTHESIS-STUTTGART | 2006年 / 20期

关键词：

indoles; Heck reaction; palladium; 2-vinylanilines; Larock's cyclisation;

D O I：

10.1055/s-2006-950223

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Traditional strategies in indole chemistry do not allow high-yielding access to some substitution patterns such as 3,5,7-trisubstituted indoles. We report in this article the efficient synthesis of this type of indole. The Heck cyclisation strategy we used allows the synthesis of 7-iodo-, 7-alkoxy-, 7-amino-, and 7-nitroindoles bearing other functionalities at the 3- and 5-positions. We believe that the mild conditions used should allow the preparation of indoles with a wide range of substituents in these two positions as shown by the synthesis of a 5-bromo-7-iodoindole. However, this strategy has some limitations in the case of very electron-deficient indoles such as a 7-nitroindole where the aromatisation of the 7-nitrodihydroindole intermediate is not complete. In this case, Larock's indole synthesis from disubstituted acetylenes proved to be more appropriate.

引用

页码：3467 / 3477

页数：11

共 52 条

[21] STUDIES IN INDOLE SERIES .3. JAPP-KLINGEMANN REACTION [J].