None-catalyst and clean synthesis of symmetric and asymmetric indoles from electrochemical oxidation of 4-aminophenol and p-phenylenediamine in the presence of malononitrile in green media

作者：Asghari Alireza^*; Ameri Mohsen; Radmannia Sepideh; Rajabi Maryam; Bakherad Mohammad; Nematollahi Davood

来源：Journal of Electroanalytical Chemistry, 2014, 733: 47-52.

DOI：10.1016/j.jelechem.2014.09.015

• Electrochemical oxidation
• p-Phenylenediamine
• 4-Amino phenol
• Michael addition
• ECECCC mechanism

The mechanism of electrochemical oxidation of p-phenylenediamine and 4-aminophenol in the presence of malononitrile, as a nucleophile is studied in a phosphate buffer solution (0.15 M) mixed with ethanol (v:v) using the cyclic voltammetry, controlled-potential coulometry and UV-spectroscopy methods. The results obtained indicate that the oxidation form of p-phenylenediamine and 4-aminophenol participate in the 1,4-michael addition reactions with malononitrile via the ECECCC mechanism (E: electrochemical and C: chemical) for the electrochemical synthesis of new indole derivatives with good yield under controlled potential conditions. The products obtained were characterized after purification by the FT-IR, H-1 NMR, C-13 NMR, mass spectroscopy and elemental analysis.

• 出版日期2014-11-1