Efficient and General Synthesis of 3‐Aminoindolines and 3‐Aminoindoles  via  Copper‐Catalyzed Three‐Component Coupling Reaction | Zendy

Chernyak Dmitri | Zendy; Chernyak Natalia | Zendy; Gevorgyan Vladimir | Zendy

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Efficient and General Synthesis of 3‐Aminoindolines and 3‐Aminoindoles via Copper‐Catalyzed Three‐Component Coupling Reaction

Author(s) -

Chernyak Dmitri,

Chernyak Natalia,

Gevorgyan Vladimir

Publication year - 2010

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201000015

Subject(s) - chemistry , catalysis , indole test , cascade , copper , alkyne , indoline , coupling reaction , amine gas treating , combinatorial chemistry , component (thermodynamics) , coupling (piping) , cascade reaction , organic chemistry , mechanical engineering , physics , chromatography , engineering , thermodynamics

An efficient three‐component coupling (TCC) reaction toward a variety of 3‐aminoindoline and 3‐aminoindole derivatives has been developed. This cascade transformation proceeds via the copper‐catalyzed coupling reaction between 2‐aminobenzaldehyde, a secondary amine, and an alkyne leading to a propargylamine intermediate which, under the reaction conditions, undergoes cyclization into the indoline core. The latter, upon treatment with a base, smoothly isomerizes into the indole. Alternatively, the indole can directly be synthesized in a one‐pot sequential reaction.

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