Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes,The Journal of Organic Chemistry

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Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-26 , DOI: 10.1021/acs.joc.9b03387
Krzysztof Górski ₁ , Justyna Mech-Piskorz ₁ , Barbara Leśniewska ₁ , Oksana Pietraszkiewicz ₁ , Marek Pietraszkiewicz ₁

Affiliation

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 OOC, nitrogen NNC, or sulfur SSC. Two of described pathways involve the photocyclization of the corresponding triene 2 as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin 14 and benzo[b]heteroole 15. 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.

中文翻译：

迈向可溶的5,10-二杂间二甲苯：5,10-二氧杂二甲苯，5,10-二异丁二烯和5,10-二杂氮杂烯的合成和反应性

以下工作介绍了三种通用方法，这是首次允许合成包含两个相同杂原子（即氧OOC，氮NNC或硫SSC）的5,10-二杂苯并二烯衍生物。所描述的两种途径涉及相应的三烯2的光环化，这是导致七环芳族体系的关键步骤。第三种方法基于茚三酮14与苯并[ b ]杂油15之间的酸性缩合。还介绍了5,10-二杂甲苯烯核的典型官能化。此外，本文讨论了三种建议的途径来接收特定的5,10-二杂间苯二酚衍生物的优点和局限性，因为到目前为止尚不适合用于获得具有任何类型杂原子分子的通用方法。

更新日期：2020-03-27

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