3939-47-7

Upstream product

• 620-84-8 4-methyldiphenylamine 
• 30214-01-8 1-azido-2-p-tolylsulfanyl-benzene 
• 98569-87-0 2-allylamino-4'-methyldiphenyl sulphide 
• 4837-33-6 o-nitrobenzenesulfenanilide 
• 106-49-0 p-toluidine 
• 57310-39-1 2-bromo-1-chloro-4-methylbenzene 
• 137-07-5 2-amino-benzenethiol 
• 108-94-1 cyclohexanone 
• 23451-96-9 2-amino-5-methylthiophenol 
• 589-92-4 1-methylcyclohexan-4-one 
• 1332939-41-9 2-((2-bromophenyl)thio)-4-methylaniline 
• 6320-02-1 o-bromothiophenol 
• 2942-15-6 6-methylbenzothiazole 
• 583-55-1 1-Bromo-2-iodobenzene 

Downstream Products

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 67-64-1 acetone 
• 33555-53-2 N-benzyl-3-(3-methyl-phenothiazin-10-yl)-propionamide 
• 33555-54-3 N-cyclohexyl-3-(3-methyl-phenothiazin-10-yl)-propionamide 

Relevant academic research and scientific papers

The influence of molecular geometry on the efficiency of thermally activated delayed fluorescence

In this work we successfully developed a strategy for positively influencing the conformation of thermally activated delayed fluorescence (TADF) molecules containing phenothiazine as the electron donor (D) unit, and dibenzothiophene-S,S-dioxide as the acceptor (A), linked in D-A and D-A-D structures. In this strategy the effect of restricted molecular geometry is explored to maximize TADF emission. The presence of bulky substituents in different positions on the donor unit forces the molecules to adopt an axial conformer where the singlet charge transfer state is shifted to higher energy, resulting in the oscillator strength and luminescence efficiency decreasing. With bulky substituents on the acceptor unit, the molecules adopt an equatorial geometry, where the donor and acceptor units are locked in relative near-orthogonal geometry. In this case the individual signatures of the donor and acceptor units are evident in the absorption spectra, demonstrating that the substituent in the acceptor uncouples the electronic linkage between the donor and acceptor more effectively than with donor substitution. In contrast with the axial conformers that show very weak TADF, even with a small singlet triplet gap, molecules with equatorial geometry show stronger oscillator strength and luminescence efficiency and are excellent TADF emitters. Acceptor-substituted molecules 6 and 7 in particular show extremely high TADF efficiency in solution and solid film, even with a singlet-triplet energy gap around 0.2 eV. This extensive study provides important criteria for the design of novel TADF and room temperature phosphorescence (RTP) emitters with optimized geometry.

Iodine/DMSO-Promoted Selective Direct Arylthiation of Anilines with Thiols under Metal-Free Conditions

An iodine-promoted divergent thiolation of unprotected anilines with thiols for the synthesis of sulfide anilines has been described. The combinational use of I2 and DMSO played an important role to realize this kind of transformation without the aid of a

A method of synthesizing phenoxthine compounds

The invention develops a method for synthesizing phenothiazine compounds by using benzothiazole and derivatives thereof as well as 1-bromo-2-iodobenzene and derivatives thereof as raw materials and copper or copper salt/N-alkoxy-1H-pyrrolic amide system as a copper catalyst. The method is a brand-new method for synthesizing phenothiazine compounds. The method has the characteristics of low temperature, short reaction time, low solvent toxicity and wide substrate adaptability, and has wide application prospects in the aspect of preparation of medicines, pesticides and materials.

Copper-Catalyzed Domino Reactions for the Synthesis of Phenothiazines

A method for the one-pot synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides was explored. Preliminary work on the mechanism of the reaction suggested that it follows a domino process, including the hydrolysis of benzothiazoles followed by C-S coupling and C-N coupling. The low loading of the catalyst system (5 mol-% for both copper and ligand), the mild experimental conditions (90 °C, 12 h), and the use of a green reaction medium make this synthesis very attractive to academia and industry. A copper-catalyzed domino reaction consisting of the hydrolysis of benzothiazoles followed by C-S and C-N couplings for the synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides is described. The low loading of the catalyst system, mild experimental conditions, and the use of polyethylene glycol as the solvent make this synthetic approach very attractive to academia and industry.

A catalyst system, copper/ N -methoxy-1 H -pyrrole-2-carboxamide, for the synthesis of phenothiazines in poly(ethylene glycol)

A copper/N-methoxy-1H-pyrrole-2-carboxamide catalyst system has been established for the preparation of phenothiazines in good yields by two routes, starting from 2-iodoanilines and 2-bromobenzenethiol and from aryl ortho-dihalides and o-aminobenzenethiols, by conducting the reaction at 90 °C in poly(ethylene glycol)-100 (PEG-100). In addition, the catalyst system was useful for promoting direct arylation of various aryl amines, aliphatic amines, and aqueous ammonia. The simple experimental operation, low loading of catalyst system together with the use of green solvent, makes it attractive for the versatile syntheses of phenothiazines and various amines.

Synthesis of phenothiazines from cyclohexanones and 2-aminobenzenethiols under transition-metal-free conditions

A convenient method for the synthesis of various substituted phenothiazines from cyclohexanones and 2-aminobenzenethiols using molecular oxygen as hydrogen acceptor in the absence of transition-metals is described. For the first time cyclohexanones were used as coupling partners for the construction of phenothiazines.

Synthesis of phenothiazines via ligand-free CuI-catalyzed cascade C-S and C-N coupling of aryl ortho-dihalides and ortho-aminobenzenethiols

A ligand-free CuI-catalyzed cascade C-S and C-N cross coupling of (hetero)aryl ortho-dihalides and ortho-aminobenzenethiols has been developed, and various phenothiazines were synthesized with excellent regioselectivity. A possible mechanism is proposed for the cascade coupling.

Synthesis and antitubercular activity of phenothiazines with reduced binding to dopamine and serotonin receptors

Analogs of the psychotropic phenothiazines were synthesized and examined as antitubercular agents against Mycobacterium tuberculosis H37Rv. The compounds were subsequently counter-screened for binding to the dopaminergic-receptor subtypes D1, D2, D3 and the serotonergic-receptor subtypes 5-HT1A, 5-HT2A, and 5-HT2C. The most active compounds showed MICs from 2 to 4 μg/mL and had overall reduced binding to the dopamine and serotonin receptors compared to chlorpromazine and trifluoperazine.

Gas-phase Rearrangement and Cyclisation Reactions of 2-Benzylphenylaminyl Radicals and Related 2-Hetero-analogues

Gas-phase pyrolysis of the appropriate N-allyl or N-benzyl compound leads to the aminyl radicals 1 (X = NH, Y = CH2, CO, S, or O).Equilibration of these via the spirodienyl 2 gives mixtures of isomeric acridans or acridones as major products from radicals 1 (X = NH, Y = CH2 and Y = CO, respectively) and isomeric phenothiazines as minor products from radical 1 (X = NH, Y = S).The major product in this case is the aminodibenzofuran 29 which may be formed by H-abstraction by the aminyl to give an aryl radical, followed by cyclisation (Scheme 6).The only cyclised product from radical 1 (X = NH, Y = O) is the carbazole 35, formed by a mechanism similar to that of Scheme 6, but in which H-abstraction by the rearranged phenoxyl radical has taken place.

New Gas Phase Reactions of Substituted Benzyl, Phenylaminyl, and Phenoxyl Radicals. Rearrangements to Fused 5- and 6-Membered Heterocyclic Systems

Flash vacuum pyrolysis studies of substituted benzyl, phenylaminyl, and phenoxyl radicals have revealed three new classes of reactions: formation of five-membered ring products via intramolecular abstracion of an aromatic hydrogen atom, formation of six-membered rings via spirodienyl radical intermediates, and isomerisation of o-phenoxybenzyl into o-benzylphenoxyl radicals and vice versa.