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Electrochemical Oxidative C?H Amination of Phenols: Access to Triarylamine Derivatives

Dehydrogenative C?H/N?H cross-coupling serves as one of the most straightforward and atom-economical approaches for C?N bond formation. In this work, an electrochemical reaction protocol has been developed for the oxidative C?H amination of unprotected phenols under undivided electrolytic conditions. Neither metal catalysts nor chemical oxidants are needed to facilitate the dehydrogenation process. A series of triarylamine derivatives could be obtained with good functional-group tolerance. The electrolysis is scalable and can be performed at ambient conditions.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Method for synthesizing N – aryl phenothiazine compounds (by machine translation)

The invention discloses a method for synthesizing N – aryl phenothiazine compounds, which belongs to the technical field of organic chemistry. In order to indole compounds 1 and phenothiazine 2 as reaction raw material, cuprous bromide as a catalyst, in a polar aprotic solvent, under the air atmosphere of the reaction, the obtained N – aryl substituted phenothiazine compounds 3. The invention using air as the oxidizing agent, with green, economic, and environmental protection, the use of the indole and phenothiazine between dehydrogenation C (sp2 ) – H/N – H cross-coupling, constructing the model C – N key, widens the N – aryl phenothiazine compound synthesis method. (by machine translation)

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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A NOVEL SYNTHETIC ROUTE TO CYANOPHENOTHIAZINES. FIRST EXAMPLE OF SMILES REARRANGEMENT FROM HALOGENOBENZONITRILES

The reaction of halogenobenzonitriles with 2-aminobenzenethiol gave, by a Smiles rearrangement 2-mercaptocyanodiphenylamines which are cyclised to cyanophenothiazines via a disulfide intermediate.A mechanism is proposed.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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A metal- and oxidizing-reagent-free anodic para-selective amination of anilines with phenothiazines

A highly para-selective amination of anilines with phenothiazines for producing various functionalized 10-aryl-10H-phenothiazines is reported. The oxidative amination reaction proceeds electrochemically at room temperature, thereby avoiding the use of metals and oxidizing reagents with excellent functional group tolerance and broad substrate scope.

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Synthesis and structure-activity relationships of phenothiazine carboxylic acids having pyrimidine-dione as novel histamine H1 antagonists

A series of phenothiazine carboxylic acid derivatives, having 6-amino-pyrimidine-2,4(1H,3H)-dione moiety via a appropriate linker, were synthesized and evaluated for their affinity toward human histamine H1 receptor and Caco-2 cell permeability. Selected compounds were further evaluated for their oral anti-histaminic activity in mice and bioavailability in rats. Finally, promising compounds were examined for their anti-inflammatory potential in mice OVA-induced biphasic cutaneous reaction model. Among the compounds tested, phenothiazineacetic acid compound 27 showed both histamine H1-receptor antagonistic activity and anti-inflammatory activity in vivo model.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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O2-mediated dehydrogenative amination of phenols

A method was developed for the direct dehydrogenative construction of C-N bonds between unprotected phenols and a series of cyclic anilines without resorting to any kind of metal activation of either substrate and without the use of halides. The resulting process relies on the exclusively organic activation of molecular oxygen and the subsequent oxidation of the aniline substrate. This allows the coupling of ubiquitous phenols, thus furnishing aminophenols through an atom-economical and most sustainable dehydrogenative amination method. This new reactivity, which relies on the intrinsic organic reactivity of cumene in what can be seen as a modified Hock activation process of oxygen, is expected to have a large impact on the formation of C-N bonds in organic synthesis.

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Electrochemical oxidation induced selective tyrosine bioconjugation for the modification of biomolecules

Directly introducing a beneficial functional group into biomolecules under mild, clean and easy-to-handle conditions is of great importance in the field of chemical biology and pharmacology. Herein, we described an electrochemical strategy to perform the bioconjugation of tyrosine residues with phenothiazine derivatives in a rapid and simple manner. In this electrochemical system, various polypeptides and proteins were successfully labelled with excellent site-and chemo-selectivity, and metals, oxidants or additives were also avoided.

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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An environment-friendly 2 – cyano phenothiazine industrial preparation method (by machine translation)

This invention provides an environment-friendly 2 – cyano phenothiazine industrial preparation method, the method uses 2 – chloro phenothiazine and cuprous cyanide as raw materials, to high boiling organic solvent as the solvent, alkali metal halide as a catalyst to the high temperature should, in the refluxing reaction before, under the protection of inert gas, including the raw materials, solvent and catalyst reaction system by azeotropic water, azeotropic water after refluxing reaction, the temperature of the reflux after the completion of the reaction, the reaction product after processing and extraction, to obtain crude, obtained after purification of the 2 – cyano phenothiazine. In order to control the amide impurity, the azeotropic water, avoids the use of phosphorus oxychloride treatment complicated process, while avoiding the use of acyl chloride or concentrated sulfuric acid dehydration to generate highly toxic gas hydrocyanic acid, is conducive to large scale industrial production. Recovery of the 1st organic solvent, can be repeated application, the production cost is reduced. (by machine translation)

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Lipophilic methylene blue analogues enhance mitochondrial function and increase frataxin levels in a cellular model of Friedreich’s ataxia

Friedreich’s ataxia (FRDA) is an autosomal recessive neurodegenerative disorder resulting from reduced expression of the protein frataxin (FXN). Although its function is not fully understood, frataxin appears to help assemble iron sulfur clusters; these are critical for the function of many proteins, including those needed for mitochondrial energy production. Finding ways to increase FXN levels has been a major therapeutic strategy for this disease. Previously, we described a novel series of methylene violet analogues and their structural optimization as potential therapeutic agents for neurodegenerative and mitochondrial disorders. Presently, a series of methylene blue analogues has been synthesized and characterized for their in vitro biochemical and biological properties in cultured Friedreich’s ataxia lymphocytes. Favorable methylene blue analogues were shown to increase frataxin levels and mitochondrial biogenesis, and to improve aconitase activity. The analogues were found to be good ROS scavengers, and able to protect cultured FRDA lymphocytes from oxidative stress resulting from inhibition of complex I and from glutathione depletion. The analogues also preserved mitochondrial membrane potential and augmented ATP production. Our results suggest that analogue 5, emerging from the initial structure of the parent compound methylene blue (MB), represents a promising lead structure and lacks the cytotoxicity associated with the parent compound MB.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Copper-Catalyzed Aerobic Oxidative Amination of Indole Derivatives via Single-Electron Transfer

An efficient and clean approach for the oxidative amination of indole derivatives with phenothiazines is developed under copper-catalyzed aerobic conditions. The reaction is carried out via the cross-coupling of indole radical cation and phenothiazine radical in air. This approach offers a new perspective in the application of phenothiazine as a nitrogen group source for C?N bond formation reactions.

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem