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An efficient and unique approach to synthesize isatin (indole-2,3-dione) from 2-aminoacetophenone under electrochemical conditions supported by I2–DMSO through C–N cross-coupling and C(sp2)–H/C(sp3)–H functionalization is presented. This synthetic method spans a wide range of substituted 2-aminoacetophenone substrates. The use of iodine as a promoter and shorter reaction times produced good to very good yields of isatin derivatives, which is a significant improvement over the reaction in a batch process. Further, hydrazones of isatin were synthesized by using hydrazine hydrate which produces electrochemically active molecules, namely isatin-hydrazones. The hydrazones of acetophenone were also obtained using the same reaction protocol. Additionally, the effect of increasing scan rate studied using cyclic voltammetry shows that the process followed a diffusion-controlled mechanism.

Graphical abstract: Electro-organic synthesis of isatins and hydrazones through C–N cross-coupling and C(sp2)–H/C(sp3)–H functionalization

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