Regioselective synthesis of 4-and 7-alkoxyindoles from 2, 3-dihalophenols: application to the preparation of indole inhibitors of phospholipase A2

…, MP Castroviejo, V Guilarte, A Pérez…

Index: Sanz, Roberto; Castroviejo, M. Pilar; Guilarte, Veronica; Perez, Antonio; Fananas, Francisco J. Journal of Organic Chemistry, 2007 , vol. 72, # 14 p. 5113 - 5118

Full Text: HTML

Citation Number: 60

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 ...