One-pot Synthesis of 2-Aminoindole through SET Oxidative Cyclization: Concise Synthesis of Tryptanthrin and
Akriti Srivastava1, Lakshmanan Palanivel1, Sundarababu Baskaran1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
Abstract:
An efficient domino approach for the synthesis of biologically important 2-aminoindole derivatives has been developed using CuBr2 -mediated SET oxidative cyclization as a key step. This one-pot multicomponent strategy utilizes readily available ethyl propiolate, tosyl azide, and substituted aryl amines as starting materials. The generality and scope of this mild method are demonstrated with a wide variety of substrates to furnish functionalized 2-aminoindoles in good yields. The synthetic power of this strategy is further exemplified in the concise synthesis of biologically important alkaloids, Phaitanthrin E and Tryptanthrin.
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