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通过烯烃活化实现的无过渡金属分子内傅克反应:一种合成某些新型呫吨衍生物的方法。

Transition-metal-free intramolecular Friedel-Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives.

作者信息

Yıldız Tülay, Baştaş İrem, Başpınar Küçük Hatice

机构信息

Istanbul University-Cerrahpaşa, Department of Chemistry, Istanbul, Avcilar, 34320, Turkey.

出版信息

Beilstein J Org Chem. 2021 Aug 30;17:2203-2208. doi: 10.3762/bjoc.17.142. eCollection 2021.

Abstract

In this work, new derivatives (substituted 9-methyl-9-arylxanthenes) of xanthene compounds () of possible biological significance were synthesized by developing a new synthesis method. In order to obtain xanthene derivatives, the original alkene compounds to be used as the starting materials were synthesized in four steps using appropriate reactions. A cyclization reaction by intramolecular Friedel-Crafts alkylation was carried out in order to synthesize the desired xanthene derivatives using the alkenes as starting compounds. The intramolecular Friedel-Crafts reaction was catalyzed by trifluoroacetic acid (TFA) and provided some novel substituted 9-methyl-9-arylxanthenes with good yields at room temperature within 6-24 hours. As a result, an alkene compound was used for activation with TFA in the synthesis of xanthene through intramolecular Friedel-Crafts alkylation for the first time.

摘要

在这项工作中,通过开发一种新的合成方法,合成了具有潜在生物学意义的新型咕吨化合物衍生物(取代的9-甲基-9-芳基咕吨)。为了获得咕吨衍生物,使用适当的反应分四步合成了用作起始原料的原始烯烃化合物。为了以烯烃为起始化合物合成所需的咕吨衍生物,进行了分子内傅克烷基化环化反应。分子内傅克反应由三氟乙酸(TFA)催化,在室温下6-24小时内以良好的产率提供了一些新型取代的9-甲基-9-芳基咕吨。结果,首次在通过分子内傅克烷基化合成咕吨的过程中使用烯烃化合物与TFA进行活化。

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