Synthesis of diarylamines in the benzo[b]thiophene series by palladium-catalyzed amination and structure-activity relationship as antibacterial agents

• Autor(es): Queiroz, Maria João R.P. ; Ferreira, Isabel C.F.R. ; Barbosa, Sandra ; Calhelha, Ricardo C. ; Estevinho, Leticia M.
• Data: 2004
• Identificador Persistente: http://hdl.handle.net/10198/3728
• Origem: Biblioteca Digital do IPB
• Tipo de Documento: Objeto de conferência
• Idioma: Inglês
• Contribuidor(es): Biblioteca Digital do IPB

Descrição

The palladium-catalyzed amination of arylhalides has become an important method for the synthesis of arylamines found in pharmaceuticals. Using this methodology we were able to synthesize several diarylamines in the benzo[b]thiophene series.Here we report the synthesis 01 differently substituted diarylamines derivatives 01 6-bromo or 6-amino- 2,3,5-trimethylbenzo[b]thiophene in good to high yields (50-90%) (Scheme), The amino precursor was prepared from the bromo compound using also a C-N palladium-catalyzed cross-coupling with benzophenone imine, followed by acidic hydrolysis in a 60% overall yield.