超声波促进离子液体中Biginelli一锅法合成苯并咪唑并[2,1-b]喹啉-6-酮

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (9): 1769.

超声波促进离子液体中Biginelli一锅法合成苯并咪唑并[2,1-b]喹啉-6-酮

赵新海, 刘晨江, 李燕萍

新疆大学化学化工学院, 理化测试中心, 石油天然气精细化工教育部重点实验室, 乌鲁木齐 830046

收稿日期:2009-12-21 出版日期:2010-09-10 发布日期:2010-09-10
通讯作者: 刘晨江, 男, 副教授, 主要从事有机合成方法学和功能杂环化合物的合成研究. E-mail: pxylcj@126.com
基金资助:
国家自然科学基金(批准号: 20662009, 20862016)资助.

One-pot Biginelli Synthesis of Benzimidazo[2,1-b]quinazolin-6-ones in Ionic Liquid Phase Under Ultrasound Irradiation

ZHAO Xin-Hai, LIU Chen-Jiang^*, LI Yan-Ping

Key Laboratory of Petroleum and Gas Fine Chemicals of Ministry of Education, Physics and Chemistry Detecting Center, School of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China

Received:2009-12-21 Online:2010-09-10 Published:2010-09-10
Contact: LIU Chen-Jiang. E-mail: pxylcj@126.com
Supported by:
国家自然科学基金(批准号: 20662009, 20862016)资助.

摘要/Abstract

摘要： 在超声波辐射下, 芳香醛、1,3-环己二酮和2-氨基苯并咪唑3组分在离子液体([bmim]Br)介质中经Biginelli反应“一锅煮”合成了一系列新型苯并咪唑并[2,1-b]喹啉-6-酮衍生物. 2-氨基苯并咪唑的使用是对经典的Biginelli反应的发展, 并且该方法具有反应条件温和、产率较高(65%～86%)及环境友好等优点. 产物经IR, ¹H NMR和元素分析确证了结构.

关键词: Biginelli反应, 苯并咪唑并[2,1-b]喹啉-6-酮, 超声波辐射, 离子液体

Abstract: A novel series of benzimidazo[2,1-b]quinazolin-6-ones derivatives was synthesized by a three-component Biginelli condensation reaction of aldehydes, 2-aminobenzimidazole and 1,3-cyclohexanedione, employing ionic liquid[bmim]Br as a solvent under ultrasound irradiation. The classical Bignelli reaction has been extended by the use of 2-aminobenzimidazole and this method has the advantages of milder reaction conditions, short reaction time(0.5 h), good yields(65%—86%) and environmental benignity. The structures of the products were characterized by IR, ¹H NMR spectra and elemental analysis.

Key words: Biginelli reaction, Benzimidazo[2,1-b]quinazolin-6-ones, Ultrasound irradiation, Ionic liquid

TrendMD:

赵新海, 刘晨江, 李燕萍. 超声波促进离子液体中Biginelli一锅法合成苯并咪唑并[2,1-b]喹啉-6-酮. 高等学校化学学报, 2010, 31(9): 1769.

ZHAO Xin-Hai, LIU Chen-Jiang*, LI Yan-Ping. One-pot Biginelli Synthesis of Benzimidazo[2,1-b]quinazolin-6-ones in Ionic Liquid Phase Under Ultrasound Irradiation. Chem. J. Chinese Universities, 2010, 31(9): 1769.

参考文献

[1]Döming A., Ugi I.. Angew. Chem. Int. Ed.[J], 2000, 39: 3168—3210 [2]Kaim L. E., Gizzi M., Grimaud L.. Org. Lett.[J], 2008, 10: 3417—3419 [3]Strübing D., Neumann H., Hübner S., Klaus S., Beller M.. Org. Lett.[J], 2005, 7: 4321—4324 [4]Biginelli P.. Gazz. Chim. Ital.[J], 1893, 23: 360—413 [5]Kappe C. O.. Eur. J. Med. Chem.[J], 2000, 35: 1043—1052 [6]Singh B. K., Mishra M., Saxena N., Yadav G. P., Maulik P. R., Sahoo M. K., Gaur R. L., Murthy P. K., Tripathi R. P.. Eur. J. Med. Chem.[J], 2008, 43: 2717—2723 [7]Deshmukh M. B., Salunkhe S. M., Patil D. R., Anbhule P. V.. Eur. J. Med. Chem.[J], 2009, 44: 2651—2654 [8]Shaabani A., Bazgir A.. Tetrahedron Lett.[J], 2004, 45: 2575—2577 [9]Stefani H. A., Oliveira C. B., Almeida R. B., Pereira C. M. P., Braga R. C., Cella R., Borges V. C., Savegnago L., Nogueira C. W.. Eur. J. Med. Chem.[J], 2006, 41: 513—518 [10]Cepanec I., Litvic＇M., Litvic＇M. F., Grüngold I.. Tetrahedron[J], 2007, 63: 11822—11827 [11]Kamal A., Krishnaji T., Azhar M. A.. Catal. Commun.[J], 2007, 8: 1929—1933 [12]Azizian J., Mohammadi A. A., Karimi A. R., Mohammadizadeh M. R.. Appl. Catal. A: Gen.[J], 2006, 300: 85—88 [13]Liu C., Wang J., Li Y.. J. Mol. Catal. A: Chem.[J], 2006, 258: 367—370 [14]Zhang X., Li Y., Liu C., Wang J.. J. Mol. Catal. A: Chem.[J], 2006, 253: 207—211 [15]FU Nan-Yan(傅南雁), YUAN Yao-Feng(袁耀锋), PANG Mei-Li(庞美丽), WANG Ji-Tao(王积涛). Chem. J. Chinese Universities(高等学校化学学报)[J], 2003, 24(1): 79—81 [16]Chen W. Y., Qin S. D., Jin J. R.. Catal. Commun.[J], 2007, 8: 123—126 [17]Li J. T., Han J. F., Yang J. H., Li T. S.. Ultrason. Sonochem.[J], 2003, 10: 119—122 [18]Salehi P., Dabiri M., Zolfigol M. A., Fard M. A. B.. Tetrahedron Lett.[J], 2003, 44: 2889—2891 [19]Tu S., Fang F., Miao C., Jiang H., Feng Y., Shi D., Wang X.. Tetrahedron Lett.[J], 2003, 44: 6153—6155 [20]Hassani Z., Islami M. R., Kalantari M.. Bioorg. Med. Chem. Lett.[J], 2006, 16: 4479—4482 [21]Deshmukh M. B., Salunkhe S. M., Patil D. R., Anbhule P. V.. J. Med. Chem.[J], 2009, 44: 2651—2654