A general and convenient synthesis of substituted quinolines by regioselective copper- or palladiumcatalyzed6-endo-dig cyclization-dehydration of 1-(2-aminoaryl)-2-yn-1-ols is reported. The crudesubstrates were easily obtained by the Grignard reaction between the appropriate alkynylmagnesiumbromide and 2-aminoaryl ketones and could be used without further purification for the subsequentcyclization step. Heteroannulation reactions were carried out in MeOH or DME as the solvent at 60 or100 °C in the presence of CuCl2 or PdX2 (in conjunction with 10 equiv of KX, X ) Cl, I) as the catalystto afford the quinoline derivatives in good to excellent isolated yields based on starting 1-(2-aminoaryl)-2-yn-1-ols (66-90%).

Novel and Convenient Synthesis of Substituted Quinolines by Copper− or Palladium−Catalyzed Cyclodehydration of 1-(2-Aminoaryl)-2-yn-1-ols

GABRIELE, Bartolo;MANCUSO R;PLASTINA, Pierluigi
2007-01-01

Abstract

A general and convenient synthesis of substituted quinolines by regioselective copper- or palladiumcatalyzed6-endo-dig cyclization-dehydration of 1-(2-aminoaryl)-2-yn-1-ols is reported. The crudesubstrates were easily obtained by the Grignard reaction between the appropriate alkynylmagnesiumbromide and 2-aminoaryl ketones and could be used without further purification for the subsequentcyclization step. Heteroannulation reactions were carried out in MeOH or DME as the solvent at 60 or100 °C in the presence of CuCl2 or PdX2 (in conjunction with 10 equiv of KX, X ) Cl, I) as the catalystto afford the quinoline derivatives in good to excellent isolated yields based on starting 1-(2-aminoaryl)-2-yn-1-ols (66-90%).
2007
Copper; Quinolines; Palladium; heterocycles; cyclization
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/158881
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