Synthesis of 3-Iminoindol-2-amines and Cyclic Enaminones via Palladium-Catalyzed Isocyanide Insertion-Cyclization

2015/04/28 by Yuanyuan Pan, Yuan-Yuan Pan, Ya-Nan Wu +9 · 4 citations
Chemistry · #Catalytic C–H Functionalization Methods #Synthesis and Characterization of Pyrroles #Multicomponent Synthesis of Heterocycles

paper · doi:10.1021/acs.joc.5b00727

Abstract

A palladium-catalyzed isocyanide insertion-cyclization using low-cost and readily accessible 2-haloanilines, 2-iodophenylethanones, and isocyanides for efficient synthesis of 3-iminoindol-2-amine and cyclic enaminone derivatives has been developed. The method features low-cost and readily accessible starting materials, reliable scalability, and bond-forming efficiency as well as simple one-pot operation, which makes this strategy highly attractive. A reasonable mechanism for forming 3-iminoindol-2-amine involved double isocyanide insertion/cyclization process is proposed.

Cited by

• Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles. [europepmc]
• Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade. [europepmc]
• Recent Advances in Palladium-Catalyzed Isocyanide Insertions. [europepmc]
• A Novel Method to Construct 2-Aminobenzofurans via [4 + 1] Cycloaddition Reaction of In Situ Generated Ortho -Quinone Methides with Isocyanides. [europepmc]

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