ハロゲン化芳香族化合物の光化学的脱ハロゲン化(2) : ハロゲン化イサチン誘導体の光化学的脱ハロゲン化

Abstract

Photochemical dehalogenation of halogenated 1-substituted 7-azaisatins in degassed solutions was investigated. Photochemical reactions of 1-alkyl-5-bromo-7-azaisatins in degassed 2-propanol gave 1-alkyl-7-azaistins and 1-alkyl-5-bromo-7-azaoxindoles. On the other hand, photochemical reactions of 1-alkyl-5-chloro-7-axaisatins in degassed 2-propanol afforded 1-alkyl-5-chloro-7-azaoxindoles which were followed by dechlorination to give 1-alkyl-7-azaoxindoles. Photoreaction of 1-(fluorobenzyl)-7-azaisatins gave selectively 1-(fluorobenzyl)-7-azaoxyindoles. Photochemical reactions of 1-(bromobenzyl)-7-azaisatins afforded 1-(bromobenzyl)-7-azaisatins which then reduced to 1-benzyl-7-azaoxindole. Photoreaction of 1-(chlorophenyl)-7-azaisatins afforded selectively 1-(chlorobenzyl)-7-azaoxindoles.