Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines

Abstract

A simple and efficient protocol for the synthesis of polysubstituted quinolines at room temperature has been developed by ligand-free Cu-catalyzed oxidative cyclization of oxime acetates with 2-aminobenzyl alcohols.

Access to 4-Trifluoromethyl Quinolines via Cu-Catalyzed Annulation Reaction of Ketone Oxime Acetates with ortho-Trifluoroacetyl Anilines under Redox-Neutral Conditions

“…Based on our experimental results and the related previous reports, a proposed reaction mechanism was postulated (Scheme ). Initially, the oxidative addition of CuI to the N–O bond of ketone oxime acetates 2 , 4 , and 7 would generate the Cu­(III)–enamine species A and the Cu­(III)–imino species B .…”

“…In recent years, ketone oxime acetates have been becoming fascinating and versatile building blocks in the construction of heterocyclic compounds, and many elegant methods have been documented . Among them, the formation of isoquinolines and quinolines has become the focus of attention.…”

“…Among them, the formation of isoquinolines and quinolines has become the focus of attention. Employing ketone oxime acetates as distinctive N–C–C splicing units to construct structurally diverse isoquinolines and quinolines has been developed (Scheme a,b). , In addition, ketone oxime acetates also could be used as C–C splicing units to participate in diverse annulation reactions . However, among these reports, only a few examples with respect to the application of ketone oxime acetates as C–C splicing units for the synthesis of quinoline compounds have been reported.…”

Synthesis of 2,3‐Disubstituted Quinoline‐4‐carbonitriles through Truce–Smiles Rearrangement of Phenacyl‐4‐nitrobenzenesulfonamides

“…In the past five years, there has been an increased interest in the synthesis of 2,3-diarylquinolines and different strategies were reported using mostly transition-metal catalysis (Figure 2). [7][8][9][10][11][12][13] In contrast, a single reported method, based on the cyclization of cis-chalcones, [14] is available for preparing of the 2,3-diarylquinoline-4-carbonitriles. Importantly, 2,3-diarylquinolines have remarkable biological properties and are antituberculotic, [15,16] antibacterial, [17,18] antiproliferative [19] and anti-inflammatory agents.…”

“…Some previously reported approaches to 2,3-diarylquinoines. [7][8][9][10][11][12][13][14] www.eurjoc.org…”