Department of Chemistry, University of Bath, Bath, BA2 7AY, UK.
Org Biomol Chem. 2021 Mar 21;19(11):2502-2511. doi: 10.1039/d0ob02567d. Epub 2021 Mar 4.
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.
愈创薁是一种烷基取代的薁，可从天然来源获得，并且是合成薁衍生物的成本低得多的起始材料，比薁本身低得多。在这里，我们报告了一种利用愈创薁 C4 位甲基质子酸性的方法来选择性官能化愈创薁。该方法产生的醛是构建取代在七元环上的薁的构建块。报告了通过烯丙基化、还原和缩合合成的该醛的衍生物，并研究了这些衍生物的一部分的变色性质。
