C4-aldehyde of guaiazulene: synthesis and derivatisation

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Guaiazulene is an alkyl-substituted azulene available from natural sources and is a much lower cost starting material for the synthesis of azulene derivatives than azulene itself. Here we report an approach for the selective functionalisation of guaiazulene which takes advantage of the acidity of the protons on the guaiazulene C4 methyl group. The aldehyde produced by this approach constitutes a building block for the construction of azulenes substituted on the seven-membered ring. Derivatives of this aldehyde synthesised by alkenylation, reduction and condensation are reported, and the halochromic properties of a subset of these derivatives have been studied.

Original languageEnglish
Pages (from-to)2502-2511
Number of pages10
JournalOrganic and Biomolecular Chemistry
Issue number11
Early online date4 Mar 2021
Publication statusPublished - 21 Mar 2021

Bibliographical note

Funding Information:
We thank the University of Bath for funding. TDJ wishes to thank the Royal Society for a Wolfson Research Merit Award and the Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University for support (2020ZD01).

Publisher Copyright:
© The Royal Society of Chemistry 2021.

Copyright 2021 Elsevier B.V., All rights reserved.

ASJC Scopus subject areas

  • Organic Chemistry


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