Electro-Organic Synthesis of 2-Amino-3-cyano-benzofuran Derivatives Using Hydroquinones and Malononitrile

Abstract

Abstract

In this work, electrochemical oxidation of hydroquinones has been studied in the presence of malononitrile as a nucleophile in aqueous solution using cyclic voltammetry and controlled potential coulometry. The results indicate that the quinones derived from hydroquinones participate in Michael addition and then intramolecular nucleophilic addition to yield benzofuran derivatives. The electrochemical synthesis of these new 2-amino-3-cyano-benzofuran derivatives has been performed successfully at a carbon-rod electrode in an undivided cell in good to excellent yields at room temperature.

Keywords:

• Benzofuran
• ECECCC mechanism
• electro-organic synthesis
• hydroquinone
• malononitrile

ACKNOWLEDGMENT

We gratefully acknowledge the financial support from the Research Council of Shahid Beheshti University.

Notes

^aVs. Ag|AgCl|KCl (3M).

^bIsolated yield.