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Method for synthesizing N-aryl-phenoxazine compounds

A technique of -aryl-, compound, applied in the field of organic synthetic chemistry

Active Publication Date: 2015-04-15
JIANGSU AOLUNDA HIGH TECH IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the methodological research on copper-catalyzed N- and O-arylation reactions has developed rapidly in recent years, none of the methodological research is dedicated to the synthesis of N-aryl-phenoxazines.

Method used

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  • Method for synthesizing N-aryl-phenoxazine compounds
  • Method for synthesizing N-aryl-phenoxazine compounds
  • Method for synthesizing N-aryl-phenoxazine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The preparation of N-phenyl-phenoxazine (formula I-a): 2-[N-(2-chlorophenyl)-amino]-phenol (formula III, 1.0mmol), CuI (0.05mmol) and Cs 2 CO 3 (3.0 mmol) and n-PrCN (2 mL) were added to a Schlenk tube. Firstly, the air was removed through three repetitions of evacuation and nitrogen injection, and then iodobenzene (1.1 mmol) was injected with a needle. After the resulting suspension was heated to reflux for 24 hours, the solids were filtered off. After removing the solvent on a rotary evaporator, the residue was purified by column chromatography [silica gel, EtOAc:petroleum ether (60-90°C)=1:99 (volume ratio)] to obtain N-phenyl-phenone in a yield of 98%. Oxazine, the structural formula is as follows:

[0048]

[0049] mp140~141℃[138–139℃; references: Gilman, H.; Moore, L.O.J.Am.Chem.Soc.1957,79,3485-3487.];

[0050] 13 C NMR (CDCl 3 )δ 143.9(2C), 138.9, 134.4, 131.0(2C), 130.8(2C), 128.4(2C), 123.2(2C), 121.2(2C), 115.4(2C), 113.2(2C).

[0051] Indicates tha...

Embodiment 2

[0053] The preparation of N-(2-methylphenyl)-phenoxazine (formula I-b): using the same conditions as in Example 1, only iodobenzene is replaced by o-iodotoluene to obtain N- (2-Methylphenyl)-phenoxazine, the structural formula is as follows:

[0054]

[0055] White crystal, mp171~173℃;

[0056] IR(KBr)ν1633, 1485, 1334, 1269, 728cm -1 ;

[0057] 13 C NMR (CDCl 3 )δ143.9(2C),138.9,136.8,133.4,132.2(2C),131.0,128.9(2C),128.6(2C),123.4(2C),121.1,115.4,112.6(2C),17.6;

[0058] HRMS(ESI-TOF)(m / z): Calculated value: [M] + 273.1148; Found: 273.1150.

[0059] Indicates that the obtained compound is correct.

Embodiment 3

[0061] The preparation of N-(3-methylphenyl)-phenoxazine (formula I-c): using the same conditions as in Example 1, only iodobenzene is replaced by m-iodotoluene to obtain N- (3-Methylphenyl)-phenoxazine, the structural formula is as follows:

[0062]

[0063] White crystal, mp123~125℃;

[0064] IR(KBr)ν1636, 1485, 1335, 1269, 732cm -1 ;

[0065] 13 C NMR (CDCl 3 )δ143.9(2C),141.2,138.8,134.4(2C),131.1,130.7,129.2,127.6,123.1(2C),121.1(2C),115.3(2C),113.2(2C),21.3;

[0066] HRMS(ESI-TOF)(m / z): Calculated value: [M] + 273.1148; Found: 273.1145.

[0067] Indicates that the obtained compound is correct.

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Abstract

The invention discloses a method for synthesizing N-aryl-phenoxazine compounds, and belongs to the chemical synthesis filed. The method comprises the following steps: taking a compound represented by the formula I, which is shown in the description, as the raw materials; mixing the compound with a solvent, a catalyst, and an alkali reagent, adding an arylation agent, and carrying out reactions at a temperature of 50 to 250 DEG C so as to obtain the target product; wherein the solvent is amides, benzenes, or nitriles; the catalyst is copper halide, cuprous halide, alkyl copper carboxylate, alkyl copper carboxylate hydrate, aryl copper carboxylate, cuprous oxide, or cuprous cyanide; and the arylation agent is iodobenzenes represented by formula II, which is shown in the description, mono-substituted iodopyridine, or 3-iodothiophene. The method has the advantages of simple reaction steps and high yield of target product.

Description

technical field [0001] The invention belongs to the field of organic synthesis chemistry, in particular to a method for synthesizing N-aryl-phenoxazine compounds. Background technique [0002] Phenoxazine structural units as electron donors widely exist in the molecules of synthetic materials, for example, they are often used in the research of optoelectronic materials such as dye-sensitized solar cells, laser dyes, fluorescent materials and organic light-emitting diodes (OLEDs). If an electron acceptor is substituted on the nitrogen atom in the phenoxazine molecule, a "donor-acceptor" structure is formed resulting in "push-pull" fluorophore or chromophore properties. Aryl groups are often used as such electron acceptors, so the importance of N-aryl-phenoxazines has gradually increased in recent years [Refs: (a) Tanaka, H.; Shizu, K.; Miyazaki, H.; Adachi, C. Chem. Commun. 2012, 48, 11392–11394. (b) Karlsson, K.M.; Jiang, X.; Eriksson, S.K.; Gabrielsson, E.; Rensmo, H.; Hag...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/38
CPCC07D265/38
Inventor 胡跃飞刘楠王歆燕陈律
Owner JIANGSU AOLUNDA HIGH TECH IND