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Pd-catalyzed amination of isomeric chloroquinolines with 1-(2-ethoxy)adamantane produced corresponding N-heteroaryl substituted amines and the yields were shown to be dependent on the position of the halogen atom in the heteroaromatic ring. Catalytic substitution of chlorine in dichloroquinolines proceeds faster in positions 2 and 4 allowing to obtain corresponding chloroquinolinyl substituted amines. Diamination of 4,7- and 4,8-dichloroquinolines with the excess of 1-(2-ethoxy)adamantane afforded diaminosubstituted quinolines in high yields.