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
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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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