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

Cu/TBHP mediated tetrahydroquinoline synthesis in water via oxidative cyclization reaction

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

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

E-mail: selva@biotech.sastra.edu

Received: 17 December 2021  Accepted: 29 August 2022

Abstract:

A series of tetrahydroquinoline derivatives were synthesized in good yields through Cu(OAc)₂/t-butyl hydroperoxide (TBHP) assisted oxidative cyclization reaction. All the reactions were carried out in the aqueous medium at room temperature itself. In the oxidative cyclization reaction, dual functionalization of C(sp³)-H and C(sp²)-H bonds of the N,N-dimethylaniline was achieved in one-pot operation under mild reaction conditions. TBHP assisted synthesis of tetrahydroquinoline analogues was also successfully performed in the aqueous KCl medium in the absence of copper catalyst.

Graphical abstract

Keywords: Tetrahydroquinoline; Green synthesis; Water; Oxidative cyclization; Salt effect

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02462-z

Chemical Papers 77 (1) 151–158 (2023)