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

Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (9): 1769.

• Articles • Previous Articles Next Articles

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.

Abstract

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:

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[J]. Chem. J. Chinese Universities, 2010, 31(9): 1769.

References

[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

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

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	CUI Wei, ZHAO Deyin, BAI Wenxuan, ZHANG Xiaodong, YU Jiang. CO₂ Absorption in Composite of Aprotic Solvent and Iron-based Ionic Liquid [J]. Chem. J. Chinese Universities, 2022, 43(8): 20220120.
[2]	PENG Kuilin, LI Guilin, JIANG Chongyang, ZENG Shaojuan, ZHANG Xiangping. Research Progress for the Role of Electrolytes in the CO₂ Electrochemical Reduction [J]. Chem. J. Chinese Universities, 2022, 43(7): 20220238.
[3]	JI Shuangqi, JIN Zhao, GUAN Wenna, PAN Xiangyu, GUAN Tong. Preparation and Chromatographic Performance of Mixed-mode Silica Stationary Phase Modified by Double Cationic Ionic Liquid and Octadecyl Group [J]. Chem. J. Chinese Universities, 2022, 43(6): 20220008.
[4]	CHANG Sihui, CHEN Tao, ZHAO Liming, QIU Yongjun. Thermal Degradation Mechanism of Bio-based Polybutylactam Plasticized by Ionic Liquids [J]. Chem. J. Chinese Universities, 2022, 43(11): 20220353.
[5]	WANG Man, WANG Xin, ZHOU Jing, GAO Guohua. Efficient Synthesis of Dimethyl Carbonate via Transesterification of Methanol and Ethylene Carbonate Catalyzed by Poly（ionic liquid）s [J]. Chem. J. Chinese Universities, 2021, 42(12): 3701.
[6]	WAN Ren, SONG Fan, PENG Changjun, LIU Honglai. Group Contribution Method for Infinite Dilution Molar Conductivity of Unconventional Ions in Water [J]. Chem. J. Chinese Universities, 2021, 42(12): 3672.
[7]	ZHOU Molin, JIANG Xin, YI Ting, YANG Xiangguang, ZHANG Yibo. Improvement of Interface Stability Between Sulfide Solid Electrolyte Li₁₀GeP₂S₁₂ and Lithium Metal [J]. Chem. J. Chinese Universities, 2020, 41(8): 1810.
[8]	CHENG Shifu,HU Hao,CHEN Bihua,WU Haihong,GAO Guohua,HE Mingyuan. Preparation and Electrochemical Performance of Porous Carbons Prepared from Binary Ionic Liquids ^† [J]. Chem. J. Chinese Universities, 2020, 41(5): 1048.
[9]	GAO Chong,YU Fengli,XIE Congxia,YU Shitao. Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Alcohol Heteropoly Acid Ionic Liquid ^† [J]. Chem. J. Chinese Universities, 2020, 41(5): 1101.
[10]	GAO Naiwei, MA Qiang, HE Yonglin, WANG Yapei. Green Electronic Devices Based on Ionic Liquids ^† [J]. Chem. J. Chinese Universities, 2020, 41(5): 901.
[11]	PIAO Huilan,MA Pinyi,QIN Zucheng,JIANG Yanxiao,SUN Ying,WANG Xinghua,SONG Daqian. Determination of Triazine Herbicides from Fruit Juice Samples Using Effervescence Assisted Microextraction Method Based on Acidic Ionic Liquid Packed Syringe [J]. Chem. J. Chinese Universities, 2020, 41(2): 228.
[12]	ZHANG Li,QIAN Mingchao,LIU Xueke,Gao Shuaitao,YU Jiang,XIE Haishen,WANG Hongbin,SUN Fengjiang,SU Xianghong. Dynamic Study of Oxidative Desulfurization by Iron-based Ionic Liquids/NHD ^† [J]. Chem. J. Chinese Universities, 2020, 41(2): 317.
[13]	WANG Nan,YAO Kaisheng,ZHAO Chenchen,LI Tianjin,LU Weiwei. Ionic Liquid-assisted Synthesis of AuPd Nanosponges and Their Catalytic Performance ^† [J]. Chem. J. Chinese Universities, 2020, 41(1): 62.
[14]	LIU Xiaozhou, GUAN Xinyu, FANG Qianrong, JIN Yongri. Three-dimensional Covalent Organic Frameworks Synthesized by Room Temperature Ionic Liquid Method^† [J]. Chem. J. Chinese Universities, 2019, 40(7): 1341.
[15]	LI Chenguang, HUA Er, LIU Tianxia. Tribological Behaviour of Protic Ionic Liquid Composed of 2-Ethylhexylethylenediaminium Cation and Trifluoromethanesulfonate Anion as Liquid Paraffin Additive^† [J]. Chem. J. Chinese Universities, 2019, 40(7): 1411.