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DOI: 10.1055/a-2383-0958
Practical Synthesis of N-Anilinylphenothiazines Using a Cyclic Hypervalent Iodine Coupling Reagent
This work was partially supported by JSPS KAKENHI Grant Number 23K06060 to K. M. and the Ritsumeikan Global Innovation Research Organization (R-GIRO) project to T. D.
Abstract
An improved protocol for the synthesis of N-anilinylphenothiazines based on the coupling reaction of anilines with phenothiazines using cyclic iodine(III) reagent is presented. In the improved method, the product can be isolated and purified without using column chromatography, and the cyclic hypervalent iodine reagent can be quantitatively recovered by aliquot manipulation. The workup procedure presented here is simpler compared to previously reported ones, facilitating large-scale synthesis. The para-selective phenothiazination of nitrogen-containing heterocycles such as hydroquinoline, which is important in pharmacology, was also successfully performed.
Key words
hypervalent iodine(III) reagent - aryl C–H amination - solid–liquid separation - coupling reaction - N-anilinylphenothiazinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2383-0958.
- Supporting Information
Publication History
Received: 02 July 2024
Accepted after revision: 08 August 2024
Accepted Manuscript online:
08 August 2024
Article published online:
19 September 2024
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