2-amino selenophenes compound and synthesis method and application thereof

A synthesis method and compound technology, applied in the direction of organic chemistry, drug combination, antibacterial drugs, etc., can solve the problems of unstable reaction, harsh reaction conditions, cumbersome reaction operation, etc., and achieve cheap and easy solubility and substrate adaptability The effect of strong sex and simple raw materials

Active Publication Date: 2021-07-23
珠海暨创硒源纳米科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These preparation methods have harsh reaction conditions and low yields, and most of the reactions use organic selenium compounds that are unstable, difficult to prepare, and have a pungent odor as selenium sources, and the reaction operations are relatively cumbersome.

Method used

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  • 2-amino selenophenes compound and synthesis method and application thereof
  • 2-amino selenophenes compound and synthesis method and application thereof
  • 2-amino selenophenes compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of compound 1

[0042]

[0043] Take 98mg of cyclohexanone and 114mg of ethyl cyanoacetate (molar ratio 1:1) in a 50mL one-necked flask, add 20mL of ethanol to dissolve, oscillate at 45°C and 40KHz for 20min, then add Na 2 Se 225mg (molar ratio 1:1:1.8), react under nitrogen protection, 45°C, 40KHz ultrasonic vibration. At the end of the reaction, the reaction solution became turbid. The reaction solution was poured into cold water, allowed to stand, and filtered to obtain a crude product, which was further purified by recrystallization with methanol to obtain 104.8 mg of compound 1 with a yield of 38.5%.

[0044] 1 H-NMR (400MHz, DMSO-d 6 )δ(ppm):8.52(2H,s),4.25(2H,m),2.29(2H,t),2.02(2H,t),1.73(2H,m),1.69(2H,m),1.35( 3H,t). 13 C-NMR (400MHz, DMSO-d 6 )δ (ppm): 166.0, 154.6, 145.0, 142.1, 109.0, 63.0, 32.1, 30.2, 28.1, 23.6, 15.8

Embodiment 2

[0046] Preparation of Compound 2

[0047]

[0048] Take 84mg of cyclopentanone and 114mg of ethyl cyanoacetate (molar ratio 1:1) in a 50mL single-necked flask, add 20mL of ethanol to dissolve, ultrasonically shake at 30°C and 40KHz for 20min, then add Na 2 Se 225mg (molar ratio 1:1:1.8), react under nitrogen protection, 30°C, 40KHz ultrasonic vibration. At the end of the reaction, the reaction solution became turbid, and the reaction solution was poured into cold water, allowed to stand, and filtered to obtain a crude product, which was further purified by recrystallization with methanol to obtain 79.8 mg of compound 2 with a yield of 30.9%.

[0049] 1 H-NMR (400MHz, DMSO-d 6 )δ (ppm): 8.49 (2H, s), 4.17 (2H, m), 2.35 (2H, t), 2.24 (2H, t), 1.92 (2H, m), 1.35 (3H, t); 13 C-NMR (400MHz, DMSO-d 6 )δ (ppm): 165.8, 149.4, 145.6, 141.3, 110.2, 60.2, 44.7, 42.5, 25.2, 12.9

Embodiment 3

[0051] Preparation of compound 3

[0052]

[0053] Take 112mg of cycloheptanone and 114mg of ethyl cyanoacetate (molar ratio 1:1) in a 50mL single-necked flask, add 20mL of ethanol to dissolve, oscillate ultrasonically at 60°C and 40KHz for 20min, then add Na 2 Se 187.5mg (molar ratio 1:1:1.5), react under nitrogen protection, 60°C, 40KHz ultrasonic vibration. At the end of the reaction, the reaction solution became turbid. The reaction solution was poured into cold water, allowed to stand, and filtered to obtain a crude product, which was further purified by recrystallization with methanol to obtain 84.2 mg of compound 3 with a yield of 29.4%.

[0054] 1 H-NMR (400MHz, DMSO-d 6 )δ(ppm):8.53(2H,s),4.29(2H,m),2.05(2H,t),1.90(2H,t),1.62(2H,m),1.84(2H,m),1.49( 2H,m),1.40(3H,t); 13 C-NMR (400MHz, DMSO-d 6 )δ (ppm): 163.1, 151.2, 142.5, 141.8, 110.0, 60.5, 31.8, 31.5, 25.6, 22.3, 15.2

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PUM

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Abstract

The invention discloses a 2-amino selenophen compound and a synthesis method and application thereof. The synthesis method adopts sodium selenide as a raw material and ultrasonic catalysis, compared with the prior art, use of a catalyst organic amine in the reaction process is avoided, and therefore complicated separation and purification operation is avoided, and the obtained compound is high in purity and environmentally friendly. The 2-aminoselenophen produced by the process has the advantages of high yield, simple process steps and mild reaction conditions, is suitable for industrial production, solves the problem of low yield in the prior art, and has strong activity of resisting multidrug-resistant bacteria.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a 2-aminoselenophene compound, its synthesis method and antibacterial application. Background technique [0002] Selenium-containing heterocyclic compounds such as selenophene compounds have a variety of biological and pharmaceutical activities, and have good optoelectronic properties due to the unique structure of selenium atoms, so they are widely used in the synthesis of new organic optoelectronic materials and drugs. The preparation of selenophene has been reported more than 80 years ago, but there is still a lack of effective preparation methods. The preparation of selenophene reported so far is still in the early preparation stage of reacting unsaturated enynes with corresponding selenium, and the reaction conditions are harsh. In 1927, Mazza et al first reported the reaction of selenium and acetylene at a high temperature of 400°C, and selenophene was detected in the pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D345/00A61P35/00A61P31/04
CPCC07D345/00A61P35/00A61P31/04Y02A50/30
Inventor 曹文强刘畅杨懋勋李海伟陈义康
Owner 珠海暨创硒源纳米科技有限公司
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