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Synthesis 2018; 50(01): 84-101
DOI: 10.1055/s-0036-1590952
DOI: 10.1055/s-0036-1590952
feature
Approaches to the Synthesis of Highly Substituted Aromatic and Fused Rings: Metal-Catalysed versus Thermal Cyclisation
A Parsons Scholarship was received by J.A.P. and L.A.T.A., with further funding from Drs. Bader (L.A.T.A.) and Anacor (J.A.P.). An Imperial College PhD Scholarship funded work completed by D.R.J. (EPSRC: 1507589). We also gratefully acknowledge the Bader scholarship received by A.C.P.Weitere Informationen
Publikationsverlauf
Received: 18. September 2017
Accepted after revision: 13. Oktober 2017
Publikationsdatum:
27. November 2017 (online)
Dedicated to Dr. Alfred Bader on the occasion of his 93rd 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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590952.
- Supporting Information
- CIF File
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