Electrogenerated base-promoted synthesis of N-benzylic rhodanine and carbamodithioate derivatives

Abstract

Electrogenerated magnesium-associated cyanomethyl anions/bases obtained from the electrochemical reduction of acetonitrile and the oxidation of a sacrificial magnesium rod were successfully used to promote the addition of carbon disulfide to primary benzylic amines. Alkylation with ethyl 3-bromopropionate acid ester or with ethyl 2-bromoacetate acid ester yields the corresponding ring-opened carbamodithioate compounds or cyclic rhodanine derivatives, respectively. The effect of the amount of electrogenerated base on the yield of reaction was also evaluated.

Keywords:

• electrogenerated bases/anions
• rhodanines
• carbamodithioates
• electrosynthesis
• cyclization
• heterocycles

Acknowledgements

The authors gratefully acknowledge the Tunisian “Ministère de l'Enseignement Supérieure, de la Recherche et la Technologie” for financial support (Lab CH-02). Bernd Schöllhorn is acknowledged for his valuable help during the preparation of the manuscript.