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An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans

Willem A. L. van Otterlo*, Garreth L. Morgans, Lee G. Madeley, Samuel Kuzvidza, Simon S. Moleele, Natalie Thornton and Charles B. de Koning

*School of Chemistry, Molecular Sciences Institute, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa, Email: willemaurum.chem.wits.ac.za

W. A. L. van Otterlo, G. L. Morgans, L. G. Madeley, S. Kuzvidza, S. S. Moleele, N. Thornton, C. B. de Koning, Tetrahedron, 2005, 61, 7746-7755.

DOI: 10.1016/j.tet.2005.05.090



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Abstract

Substituted benzofurans were synthesized from their corresponding substituted 1-allyl-2-allyloxybenzenes using ruthenium-catalyzed C- and O-allyl isomerization followed by ring-closing metathesis.

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Details

The document details a novel method for synthesizing substituted benzofurans using an isomerization-ring-closing metathesis (RCM) strategy. Researchers from the University of the Witwatersrand synthesized twelve substituted benzofurans from their corresponding 1-allyl-2-allyloxybenzenes. The process involves ruthenium-mediated C- and O-allyl isomerization followed by RCM. This method is significant due to its novelty in isomerizing mixed C- and O-allyl systems and performing RCM on C-vinylic and O-vinylic groups. The study demonstrated the method's efficiency and versatility, tolerating various substituents, including electron-withdrawing groups like nitro and aldehyde, which are useful for further functional modifications. The yields of the final benzofuran products varied, with some reactions achieving up to 100% yield. The research highlights the potential of this approach in medicinal chemistry, given the biological relevance of benzofurans. The document also includes detailed experimental procedures and characterizations of the synthesized compounds. The work was supported by the National Research Foundation and the University of the Witwatersrand, with acknowledgments to various contributors and funding sources.


Key Words

Benzofurans, Isomerizations, Ring-closing metathesis, Enol Ethers


ID: J72-Y2005-3010