Synthesis of 2,4-Disubstituted Quinoline Derivatives via A³-Coupling: An EcoScale Evaluation

Abstract

The 2,4-disubstituted quinoline moiety is an important building block for numerous biologically active and industrially useful compounds. These elegant compounds can be synthesised via the three-component coupling between an aldehyde, amine, and alkyne commonly referred to as A³-coupling. This short review aims to give an overview of the progress made towards disubstituted quinoline derivatives using this innovative methodology.

1 Introduction

2 Applications of the Quinoline Moiety

2.1 Antimicrobial Properties

2.2 Anti-inflammatory Properties

2.3 Anticonvulsant Properties

2.4 Photophysical Properties

3 Synthesis Based on A³-Coupling

3.1 Copper-Catalysed Systems

3.2 Iron-Catalysed Systems

3.3 Miscellaneous Systems

3.3.1 Montmorillonite Clays

3.3.2 Polyoxometalates

3.3.3 Rare Earth Metals

3.3.4 Al₂O₃ Nanoparticles/Methanesulfonic Acid

4 Proposed Reaction Mechanism

5 EcoScale Evaluation

6 Conclusion

7 Appendix

Keywords

A³-coupling - disubstituted - ecoscale - quinolone - synthesis

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