Reaction of 1,2-indanedione with 3,5-dimethoxyaniline

Abstract

1,2-Indanediones are a new class of fluorogenic reagents for amino acid visualization. In order to better understand the mechanism of formation of the resulting fluorescent products, we have examined the reactions of 1,2-indanediones with amino compounds. Treatment of 1,2-indanedione with 3,5-dimethoxyaniline in benzene afforded several products. The initial mode of addition occurred through attack of nitrogen at the C-2 position of the 1,2-indanedione generating an enamine which underwent subsequent reactions.