Alkyl aryl asymmetric azo and synthesis method thereof

A technique for the synthesis of alkyl aryl groups, which is applied in the field of alkyl aryl asymmetric azo and its synthesis, can solve the problems of increasing cytotoxicity and increasing the concentration of cisplatin in cells, and achieves good research and application value Effect

Active Publication Date: 2021-06-11
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, sulfasalazine is often used in the treatment of ulcerative colitis; azodiolenium salt NO donor drugs have inhibitory effects on cardiov...

Method used

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  • Alkyl aryl asymmetric azo and synthesis method thereof
  • Alkyl aryl asymmetric azo and synthesis method thereof
  • Alkyl aryl asymmetric azo and synthesis method thereof

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Experimental program
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Embodiment 1

[0018]

[0019] Diazonium p-methoxybenzenetetrafluoroborate (2.20g, 10mmol), 1-pentene (1.40g, 20mmol), azidotrimethylsilane (2.30g, 20mmol) and 9-trimethylphenyl- 10-Methylacridine perchlorate (411mg, 0.1mmol) was added to the reaction flask, dichloromethane (50g) was added to dissolve it, and a 10W blue LED light was used as the light source for illumination, and the reaction was stirred at room temperature for 15 minutes. After the reaction was completed, a saturated aqueous sodium bicarbonate solution (50 g) was added to quench the reaction, dichloromethane (50 g) was added, and after sufficient stirring, the mixture was allowed to stand for layering. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain a brown crude product. The crude product was purified by column method (eluent: ethyl acetate / petroleum ether=1:50, v / v) to obtain 2.35 g of the target product as a dark yellow liquid with a yield of 95%. 1 HNMR (500MHz, ...

Embodiment 2

[0021]

[0022] Diazonium p-methoxybenzenetetrafluoroborate (2.20g, 10mmol), 1-hexene (1.68g, 20mmol), azidotrimethylsilane (2.30g, 20mmol) and 9-trimethylphenyl- 10-Methylacridine perchlorate (411mg, 0.1mmol) was added to the reaction flask, dichloromethane (50g) was added to dissolve it, and a 10W blue LED light was used as the light source for illumination, and the reaction was stirred at room temperature for 15 minutes. After the reaction was completed, a saturated aqueous sodium bicarbonate solution (50 g) was added to quench the reaction, dichloromethane (50 g) was added, and after sufficient stirring, the mixture was allowed to stand for layering. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain a brown crude product. The crude product was purified by column method (eluent: ethyl acetate / petroleum ether=1:50, v / v) to obtain 2.4 g of the target product as dark yellow liquid with a yield of 92%. 1 HNMR (500MHz, CDCl...

Embodiment 3

[0024]

[0025] Diazonium p-methoxybenzenetetrafluoroborate (2.20g, 10mmol), 1-octene (2.24g, 20mmol), azidotrimethylsilane (2.30g, 20mmol) and 9-mesityl- 10-Methylacridine perchlorate (411mg, 0.1mmol) was added to the reaction flask, dichloromethane (50g) was added to dissolve it, and a 10W blue LED light was used as the light source for illumination, and the reaction was stirred at room temperature for 15 minutes. After the reaction was completed, a saturated aqueous sodium bicarbonate solution (50 g) was added to quench the reaction, dichloromethane (50 g) was added, and after stirring, the mixture was allowed to stand for layering. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain a brown crude product. The crude product was purified by column method (eluent: ethyl acetate / petroleum ether=1:50, v / v) to obtain 2.75 g of dark yellow liquid with a yield of 95%. 1 H NMR (500MHz, CDCl 3 )δ7.64(d, J=8.5Hz, 2H), 6.88(d, J=8...

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Abstract

The invention discloses alkylaryl asymmetric azo and a synthesis method thereof. The structural formula of the alkylaryl asymmetric azo is shown as a formula (IV). According to the synthesis method of the alkylaryl asymmetric azo, diazonium tetrafluoroborate, olefin and trimethylsilyl azide are used as raw materials, dichloromethane and other organic solvents are used as reaction solvents at normal temperature, a common blue LED lamp is used as a light source, reaction is carried out in the presence of a photocatalyst, and the alkylaryl asymmetric azo is synthesized through a three-component cascade reaction. The synthesis method provided by the invention has the advantages of mild reaction conditions, simple experimental operation, good reaction selectivity, high product yield, easy product separation and the like.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical and chemical intermediates, and in particular relates to an alkylaryl asymmetric azo and a synthesis method thereof. Background technique [0002] As an important compound intermediate, aromatic azo compounds are widely used in many fields such as organic dyes, biomedicine, food additives, free radical inducers, liquid crystal materials and nonlinear optical materials. For example, sulfasalazine is often used in the treatment of ulcerative colitis; azodiolenium salt NO donor drugs have inhibitory effects on cardiovascular treatment, anti-inflammation and anti-tumor, etc., and increase intracellular Platinum drug concentration, thereby increasing its cytotoxicity. These all reflect the application value of azo compounds and their derivatives in the field of pharmaceutical research. However, how to construct arylazo derivatives in one step through green, simple and mild reactio...

Claims

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Application Information

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IPC IPC(8): C07C247/04C07C247/10C07C253/30C07C255/65C07C303/30C07C309/73C07B53/00
CPCC07C247/04C07C247/10C07C253/30C07C255/65C07C303/30C07C309/73C07B53/00C07B2200/07
Inventor 章鹏飞沈佳斌李万梅徐骏
Owner HANGZHOU NORMAL UNIVERSITY
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