p-TSA·H₂O-Catalyzed Synthesis of 2,3-Diarylquinoline Derivatives via One-Pot Three-Component Reaction

This work is dedicated to my mentor Prof. Goverdhan Mehta, University Distinguished Professor & Dr. Kallam Anji Reddy Chair Professor, School of Chemistry, University of Hyderabad, on the occasion of his 80^th Birthday

Abstract

An environmentally benign synthesis of 2,3-diarylquinolines is reported via a one-pot three-component reaction from arylamines, benzaldehyde, and styrene oxide in the presence of 20 mol% p-TSA·H₂O at 120 °C. This protocol does not require metal catalysts, additives, and extra oxidants. Mechanistic studies confirm the crucial role of p-TSA·H₂O and the use of air as the sole oxidant makes this transformation very attractive. The salient feature of this protocol is easy handling, broad substrates scope, shorter reaction time, high atom economy, regioselectivity, and good yields; and the formation of one C–N and two C–C bonds takes place in a single step.

Keywords

arylamines - styrene oxides - aromatic aldehydes - 2,3-diaryl quinolines - environmentally benign synthesis - p-TSA·H₂O - atomic economy - three-component reaction

Publication History

Received: 15 February 2023

Accepted after revision: 07 June 2023

Accepted Manuscript online:
07 June 2023

Article published online:
05 July 2023

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