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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.