Synthesis of 1,3-Diaryl-2-methoxyindenes by Hydriodic Acid-Catalyzed Cyclization of Aryl[2-(1-aryl-2-methoxyvinyl)phenyl]methanols

摘要

An efficient two-step method for the synthesis of 1,3-diaryl-2-methoxyindenes from 1-(1-aryl-2-methoxyvinyl)-2-bromobenzenes has been developed. Thus, the reaction of 2-(1-aryl-2-methoxyvinyl)phenyllithiums, generated in situ by halogen-lithium exchange between 1-(1-aryl-2-methoxyvinyl)-2-bromobenzenes and butyllithium, with aromatic aldehydes gives aryl[2-(1-aryl-2-methoxyvinyl)phenyl]methanols, which in turn are treated with a catalytic amount of concentrated hydriodic acid to afford the corresponding 1,3-diaryl-2-methoxyindenes in reasonable yields.