RESUMO
An iodine-catalyzed regioselective sulfenylation of imidazo[1,5-a]quinolines was developed under metal- and oxidant-free reaction conditions. Using disulfides or thiophenols as sulfenylating agents, 3-sulfenylimidazo[1,5-a]quinoline derivatives were obtained in good to excellent yields with broad functional group tolerance. A multi-component reaction to generate 1-sulfenylated imidazo[1,5-a]pyridines is also described. Preliminary biological evaluation showed that some of the 3-sulfenylated imidazo[1,5-a]quinolines had significant anticancer activity.
Assuntos
Antineoplásicos/farmacologia , Iodo/química , Quinolinas/farmacologia , Compostos de Sulfidrila/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Catálise , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Quinolinas/síntese química , Quinolinas/química , Relação Estrutura-Atividade , Compostos de Sulfidrila/síntese química , Compostos de Sulfidrila/químicaRESUMO
A copper-promoted cascade reaction of 2-methylazaarenes and benzylamines has been developed via sequential double oxidative C(sp(3))-H aminations. This protocol provides straightforward access to imidazo[1,5-a]quinoline derivatives without employing prefunctionalized substrates.