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探索一种异常现象:通过7-氮杂吲哚酚中间体合成7,7'-二氮杂靛玉红。

Exploring an anomaly: the synthesis of 7,7'-diazaindirubin through a 7-azaindoxyl intermediate.

作者信息

Shriver James A, Wang Katelyn R, Patterson Andrew C, DeYoung James R, Lipsius Richard J

机构信息

Central College 812 University St. Pella IA 50219 USA

出版信息

RSC Adv. 2020 Oct 6;10(60):36849-36852. doi: 10.1039/d0ra07144g. eCollection 2020 Oct 1.

Abstract

Two independent methods generating 7-azaindoxyl as an intermediate verify that 7,7'-diazaindirubin is formed exclusively over 7,7'-diazaindigo. This contrasts with long-standing knowledge related to the reactivity of indoxyl, which proceeds a radical-initiated homodimerization process, leading to indigo. A series of experiments confirms 7-azaindoxyl as an intermediate with results suggesting a condensation pathway followed by oxidation.

摘要

两种独立的方法生成7-氮杂吲哚酚作为中间体,证实7,7'-二氮杂靛玉红是唯一由7,7'-二氮杂靛蓝形成的产物。这与长期以来关于吲哚酚反应性的认知形成对比,后者通过自由基引发的同二聚化过程生成靛蓝。一系列实验证实7-氮杂吲哚酚是中间体,结果表明其反应途径是先缩合后氧化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/48a8/9057083/8e7df345067f/d0ra07144g-f1.jpg

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