Approaches to the Synthesis of Highly Substituted Aromatic and Fused Rings: Metal-Catalysed versus Thermal Cyclisation

Philip J. Parsons; Lewis A. T. Allen; Daniel R. Jones; Alex C. Padgham; James A. Pryke; Joseph McKenna; Daniel O’Reilly

doi:10.1055/s-0036-1590952

Synthesis, Table of Contents

Synthesis 2018; 50(01): 84-101
DOI: 10.1055/s-0036-1590952

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Approaches to the Synthesis of Highly Substituted Aromatic and Fused Rings: Metal-Catalysed versus Thermal Cyclisation

Philip J. Parsons*

^aDepartment of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK Email: p.parsons@imperial.ac.uk

,

Lewis A. T. Allen

^aDepartment of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK Email: p.parsons@imperial.ac.uk

,

Daniel R. Jones

^aDepartment of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK Email: p.parsons@imperial.ac.uk

,

Alex C. Padgham

^aDepartment of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK Email: p.parsons@imperial.ac.uk

,

James A. Pryke

^bDivision of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton, BN1 9QJ, UK

,

Joseph McKenna

^bDivision of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton, BN1 9QJ, UK

,

Daniel O’Reilly

^aDepartment of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK Email: p.parsons@imperial.ac.uk

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Abstract

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Dedicated to Dr. Alfred Bader on the occasion of his 93^rd birthday and in memory of Oxana Bennett

Abstract

A domino reaction has been used for the construction of lactonamycin derivatives. This research led to a comparison study between palladium-mediated cascade cyclisations and thermal alkyne [2+2+2] cyclisations. A palladium-mediated cyclisation of alkenyl bromides with alkynes and furans has been shown to furnish highly substituted aromatic rings. Penta- and hexasubstituted aromatic rings have also been prepared by the thermolysis of suitably substituted alkynes under microwave conditions. Tetrasubstituted pyridines can also be prepared using nitriles instead of alkynes. This work will provide a new and interesting array of drug templates; mechanistic details are discussed for both reaction series.

Key words

alkynes - aromatic rings - cyclisation - thermolysis - palladium

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References

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