Features of the synthesis of isatins and isoindigo derivatives bearing long-chain haloalkyl substituents

Abstract

The features of the synthesis of long-chain isatin and isoindigo derivatives were demonstrated by the example of bromododecyl representatives. It was shown that the synthesis of bromododecylisatin was accompanied by the formation of the bis-isatin even at low temperatures. The deoxygenation of 1-(12-bromododecyl)isatin by tris(diethylamino)phosphine led to the formation of novel bis(bromoalkyl)isoindigo which easily reacted with nucleophilic reagents resulting in amino- or chloro-derivatives and phosphonium salts. The reaction of 1,1′-bis(bromododecyl)isoindigo with isatin sodium salt in slightly alkaline medium afforded mainly IZIN-12 and bis(2,3-dioxindolin-1-yl)isoindigo. In addition, several unexpected products were separated from this reaction. .