Górski Krzysztof, Mech-Piskorz Justyna, Leśniewska Barbara, Pietraszkiewicz Oksana, Pietraszkiewicz Marek
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland.
J Org Chem. 2020 Apr 3;85(7):4672-4681. doi: 10.1021/acs.joc.9b03387. Epub 2020 Mar 26.
The following work presents three general approaches allowing, for the first time, the synthesis of 5,10-diheterotruxene derivatives containing two identical heteroatoms, namely, oxygen , nitrogen , or sulfur . Two of described pathways involve the photocyclization of the corresponding triene as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin and benzo[]heteroole . Typical functionalizations of the 5,10-diheterotruxene core have also been presented. In addition, the article discusses the advantages and limitations of the three suggested paths for receiving specific 5,10-diheterotruxene derivatives because the universal method suitable for obtaining molecules with any type of heteroatoms is not known so far.
以下工作首次提出了三种通用方法，可用于合成含有两个相同杂原子（即氧、氮或硫）的5,10 - 二杂苊烯衍生物。所描述的两条途径涉及相应三烯的光环化反应，这是通向七环芳香体系的关键步骤。第三种方法基于茚三酮与苯并[]杂环烯烃之间的酸性缩合反应。文中还介绍了5,10 - 二杂苊烯核心的典型官能团化反应。此外，本文讨论了获得特定5,10 - 二杂苊烯衍生物的三种建议途径的优缺点，因为目前还不知道适用于获得含有任何类型杂原子分子的通用方法。
