6-取代-2,4-喹唑啉二酮衍生物的合成
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摘要
以邻氨基苯甲酸衍生物氰酸钾为原料,合成得到相应的脲衍生物,然后,用氢氧化钠环化,得到亚苯甲酰基脲的钠盐。最后,用盐酸调节p H,得到目标产物6-取代-2,4-喹唑啉二酮衍生物。这是一种环保高效的方法,因为所有的反应均在水中进行,并且简单地通过过滤获得所需的产物。通过核磁共振(NMR)对产物进行了表征。
The reactions of anthranilic acid derivatives with potassium cyanate afforded the corresponding urea derivatives. Then, cyclization of the urea derivatives with Na OH afforded the monosodium salts of benzoylene urea. Finally, adjuste PH with hydrochloric acid afforded the desired product 6-substituted-2,4-quinazoline-dione derivatives. This is an eco-efficient method because all the reactions were carried out in water, and the desired products were obtained simply by filtration.The target product was confirmed by NMR.
The reactions of anthranilic acid derivatives with potassium cyanate afforded the corresponding urea derivatives. Then, cyclization of the urea derivatives with Na OH afforded the monosodium salts of benzoylene urea. Finally, adjuste PH with hydrochloric acid afforded the desired product 6-substituted-2,4-quinazoline-dione derivatives. This is an eco-efficient method because all the reactions were carried out in water, and the desired products were obtained simply by filtration.The target product was confirmed by NMR.
引文
[1]方莎莎,刘小宇,焦炳华.喹唑啉酮及其衍生物的生物学活性研究进展[J].天然产物研究与开发,2015,27:1972-1978.
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[6]Mahnaz Sharafi-Kolkeshvandi,Farzad Nikpour.A facile and convenient approach for the one-pot synthesis of 2,4(1 H,3H)-quinazolinediones[J].Chinese Chemical Letters,2012,23:431-433.
[7]Xin-Chuan Tian,Xing Huang,Dan Wang,et al.Eco-Efficient One-Pot Synthesis of Quinazoline-2,4(1 H,3 H)-diones at Room Temperature in Water[J].Chem Pharm Bull,2014,62(8):824-829.
[2]Giovanni Marzaro,Adriano Guiotto,Adriana Chilin.Quinazoline derivatives as potential anticancer agents:a patent review[J].Expert Opin Ther Pat,2012,22:223-252.
[3]Dan Wang,Feng Gao.Quinazoline derivatives:synthesis and bioactivities[J].Chem Cent J,2013,7:95.
[4]Farzad Nikpour,Touraj Paibast.A Green,Facile,and One-pot Synthesis of 2,4-(1 H,3 H)-Quinazolinediones under Microwave Irradiations[J].Chemistry Letters.2005,34(10):1438-1439.
[5]Jian Gao,Liang-Nian He,Cheng-Xia Miao,et al.Chemical fixation of CO2:efficient synthesis of quinazoline-2,4(1 H,3 H)-diones catalyzed by guanidines under solvent-free conditions[J].Tetrahedron.2010,66:4063-4067.
[6]Mahnaz Sharafi-Kolkeshvandi,Farzad Nikpour.A facile and convenient approach for the one-pot synthesis of 2,4(1 H,3H)-quinazolinediones[J].Chinese Chemical Letters,2012,23:431-433.
[7]Xin-Chuan Tian,Xing Huang,Dan Wang,et al.Eco-Efficient One-Pot Synthesis of Quinazoline-2,4(1 H,3 H)-diones at Room Temperature in Water[J].Chem Pharm Bull,2014,62(8):824-829.