A novel one-pot synthesis of highly diverse indole scaffolds by the Ugi/Heck reaction

被引：56

作者：

Kalinski, Cedric

Umkehrer, Michael

Schmidt, Juergen

Ross, Guenther

Kolb, Juergen

Burdack, Christoph

Hiller, Wolfgang

Hoffmann, Stephan D.

机构：

[1] Priaton GmbH, D-82327 Tutzing, Germany

[2] Tech Univ Munich, D-85747 Garching, Germany

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 27期

关键词：

Ugi-reaction; Ugi-Heck reaction; indole; isocyanide-based multi-component reactions (IMCRs) combinatorial chemistry;

D O I：

10.1016/j.tetlet.2006.04.127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel one-pot two-step Multi component reaction of acrylic aldehydes, bromoanilines, acids and isocyanides yielding polysubstituted indoles is described. The reaction is based on the combination of an Ugi four-component reaction followed by an intramolecular Heck-reaction. The simultaneous use of formic acid and cinnamaldehydes affords in situ generation of 1H-indoles. Convertible isocyanides can also be used with success in this Ugi/Heck strategy and enable synthesis of 1H-indole-2-carboxylic acid building blocks. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4683 / 4686

页数：4

共 15 条

[1] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].