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%).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
