Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline...

• Author(s): Takács, Attila ; Szilágyi, Antal ; Ács, Péter ; Márk, László ; Peixoto, Andreia F. ; Pereira, Mariette M. ; Kollár, László
• Date: 2011
• Persistent ID: http://hdl.handle.net/10316/21203
• Origin: Estudo Geral - Universidade de Coimbra
• Subject(s): Iodo-aromatics; 8-Hydroxyquinoline; Aminocarbonylation; Carbon monoxide; Palladium
• Document Type: Article
• Language: English

Description

Various 5-carboxamido-7-iodo-8-benzyloxyquinolines were synthesised via selective aminocarbonylation of 5,7-diiodo-8-benzyloxyquinoline in the presence of ‘in situ’ generated palladium(0) catalysts. Under similar conditions (50 °C, 80 bar CO), 5,7-bis(N-tert-butyl-glyoxylamido)-8-hydroxyquinoline was obtained using tert-butylamine as N-nucleophile. The unprotected 5,7-diiodo-8-hydroxyquinoline underwent dehydroiodination resulting in 8-hydroxyquinoline as the major product.