One-Pot Three-Component Catalytic Synthesis of Fully Substituted Pyrroles from Readily Available Propargylic Alcohols, 1,3-Dicarbonyl Compounds and Primary Amines

✍ Scribed by Victorio Cadierno; José Gimeno; Noel Nebra

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 328 KB
• Volume: 13
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200701132

✦ Synopsis

Abstract

A simple and highly efficient method for the preparation of fully substituted pyrroles, from readily accessible secondary propargylic alcohols, 1,3‐dicarbonyl compounds and primary amines, has been developed. The one‐pot multicomponent reaction, which is catalysed by the system [Ru(η^3^‐2‐C~3~H~4~Me)(CO)(dppf)][SbF~6~]/CF~3~CO~2~H (dppf: 1,1′‐bis(diphenylphosphanyl)ferrocene), involves initial propargylation of the 1,3‐dicarbonyl compound promoted by CF~3~CO~2~H and subsequent condensation between the resulting γ‐keto alkyne and the primary amine to afford a propargylated β‐enamino ester or ketone, which undergoes a ruthenium‐catalysed 5‐exo‐dig annulation to form the final pyrrole.