ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

To cyclize or not? Synthesis of heterocycles through electro-oxidation of N,N-\(\hbox {dimethylaniline}^\dag\)

Marimuthu Lakshmipriya, Bommireddy Naveen, Subramaniyan Prasanna Kumari, Subramaniapillai Selva Ganesan, and Palathedath Suresh Kumar

Department of Chemistry, School of Chemical & Biotechnology, SASTRA Deemed University, Thanjavur, India

E-mail: selva@biotech.sastra.edu

Received: 28 March 2024  Accepted: 9 November 2024

Abstract:

Abstract

Herein, we report electron-mediated Povarov-type cyclization reaction using N,N-dimethylaniline as an electrochemically active substrate, with N-arylmaleimide. The results indicated that under electrochemical condition, the reaction could be completed within about 30 min. with good yield compared to the requirement of longer reaction time under chemical conditions. The role of t-butyl hydroperoxide, nature of electrodes, types of substituents as well as reaction pathways were evaluated to obtain highest yield.

Graphic Abstract

Keywords: Electro-organic synthesis; N,N-Dimethylaniline; N-Arylmaleimide; t-Butyl hydroperoxide; Povarov-type reaction; Heterocycles

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-024-03807-6

Chemical Papers 79 (2) 715–722 (2025)