Domino or Single-Step Tsuji–Trost/Heck Reactions and Their Application in the Synthesis of 3-Benzazepines and Azepino[4,5-b]indole Ring Systems

✍ Scribed by Scott G. Stewart; Charles H. Heath; Emilio L. Ghisalberti

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 256 KB
• Volume: 2009
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200900028

✦ Synopsis

Abstract

A series of methods for palladium‐mediated single‐step and domino Tsuji–Trost/Heck reactions are described. These methods are applied to the synthesis of both 3‐benzazepines and azepino[4,5‐b]indoles in the category of complex 6‐7‐6 and 6‐5‐7 ring heterocycles. In addition, a domino Heck/Heck sequence of reactions that produces the azepinobenzindolizine tetracyclic ring system from N‐diallylated precursors is described. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)