Collect. Czech. Chem. Commun. 1992, 57, 1516-1520

Reaction of Dimethylaminoethyl Derivatives of 1-Benzylidenisoindolin-3-one with Epoxides

Bohumil Proksa, Bohumil Steiner, Stanislava Uhrínová and Miroslav Koóš

Institute of Chemistry, Slovak Academy of Sciences, 842 38 Bratislava


Derivatives of 1-(2-(2-dimethylaminoethyl)benzyliden)isoindolin-3-one underwent deamination on reaction with epoxides under mild conditions. Amide group of the substrate reacted slower with epoxide than the dimethylamino grouping whilst the alkanolamide was formed with a great excess of the epoxide only. Of epoxides used in this reaction 1,2-epoxy-3-phenoxypropane, 3-decyloxypropane and 3-chloro-1,2-epoxypropane, the first was found to react most rapidly.