Regioselective synthesis of 4- and 7-alkoxyindoles from 2,3-dihalophenols: application to the preparation of indole inhibitors of phospholipase A2 |
| |
Authors: | Sanz Roberto Castroviejo M Pilar Guilarte Verónica Pérez Antonio Fañanás Francisco J |
| |
Institution: | Departamento de Química, Area de Química Orgánica, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Ba?uelos s/n, 09001-Burgos, Spain. rsd@ubu.es |
| |
Abstract: | An efficient and regioselective synthesis of 4- and 7-alkoxyindoles has been developed from commercially available starting materials such as 3-halophenols and 3-chloroanisole. Directed ortho-metalation followed by two palladium-catalyzed processes, a Sonogashira coupling and a tandem amination/cyclization reaction, allows the synthesis of regiochemically pure 4- and 7-substituted indoles. This strategy has been successfully applied to the preparation of 2-3-(2-amino-2-oxoacetyl)-1-benzyl-2-ethyl-1H-indol-4-yloxy]acetic acid (LY315920), a known inhibitor of phospholipase A2. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|