Research Progress on Green Synthesis of Imidazo[1,2-a]pyridine Compounds

doi:10.6023/cjoc201809034

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1304-1315.DOI: 10.6023/cjoc201809034 Previous Articles Next Articles

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咪唑并[1,2-a]吡啶化合物绿色合成的研究进展

赵鑫雨^a, 丁扬扬^a, 吕英涛^b, 康从民^a

a 青岛科技大学化工学院青岛 266042;
b 青岛科技大学海洋学院青岛 266042

收稿日期:2018-09-27 修回日期:2018-11-24 发布日期:2019-01-10
通讯作者: 康从民 E-mail:qustndds@163.com
基金资助:
海洋生物活性物质和现代分析技术的关键实验室（No.MBSMAT-2017-06）资助项目.

Research Progress on Green Synthesis of Imidazo[1,2-a]pyridine Compounds

Zhao Xinyu^a, Ding Yangyang^a, Lü Yingtao^b, Kang Congmin^a

a College of Chemical Engineering, Qingdao University of Science and Technology, Shandong Province, Qingdao 266042;
b Ocean College, Qingdao University of Science and Technology, Shandong Province, Qingdao 266042

Received:2018-09-27 Revised:2018-11-24 Published:2019-01-10
Contact: 10.6023/cjoc201809034 E-mail:qustndds@163.com
Supported by:
Project supported by the Key Laboratory of Marine Bioactive Substance and Modern Analytical Technique (No. MBSMAT-2017-06).

Imidazo[1,2-a]pyridine compounds were 5- and 6-membered nitrogen heterocyclic compounds, which were found in various natural products and exhibited a wide range of pharmacological activities, and were widely used in medical chemistry. Imidazo[1,2-a]pyridines have important research significance and broad medical application prospects, so the synthetic strategy literatures on the diversity of such compounds have been continuously reported. In recent years, green chemistry was one of the hot trends in contemporary chemistry. More and more attention is paid to green synthesis and constantly developing various green synthesis solutions. Among them, one-pot "multi-component" reaction, microwave reaction and solid phase synthesis, which were green and high-efficiency synthetic methods, have been the focus of research. From the three types of green synthesis methods, The research progress of imidazole[1,2-a]pyridine green synthesis in recent years is summarized.

Key words: green synthesis, one pot "multi-component reaction", microwave reaction, solid phase synthesis

Cite this article

Zhao Xinyu, Ding Yangyang, Lü Yingtao, Kang Congmin. Research Progress on Green Synthesis of Imidazo[1,2-a]pyridine Compounds[J]. Chin. J. Org. Chem., 2019, 39(5): 1304-1315.

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[1] Goel, R.; Luxami, V.; Paul, K. Curr. Top. Med. Chem. 2016, 16, 3590.
[2] Senn-Bilfinger, J.; Ferguson, J. R.; Holmes, M. A.; Lumbard, K. W.; Huber, R.; Zech, K.; Hummel, R. P.; Zimmermann, P. J. Tetrahedron Lett. 2006, 47, 3321.
[3] Bagdi, A. K.; Rahman, M.; Santra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1741.
[4] Enguehard-Gueiffier, C.; Gueiffier, A. Mini-Rev. Med. Chem. 2007, 7, 888.
[5] Trapani, G.; Franco, M.; Ricciardi, L.; Latrofa, A.; Genchi, G.; Sanna, E.; Tuveri, F.; Cagetti, E.; Biggio, G.; Liso, G. J. Med. Chem. 1997, 40, 3109.
[6] Chernyak, N.; Gevorgyan, V. Angew. Chem. 2010, 122, 2803.
[7] Dheer, D.; Reddy, K. R.; Rath, S. K.; Sangwan; P. L.; Das, P.; Shankar, R. RSC Adv. 2016, 47, 38033.
[8] Liu, L.-H. Contemp. Chem. Eng. Res. 2012, 9, 1(in Chinese). (刘丽华, 当代化工研究, 2012, 9, 1.)
[9] Akbarzadeh, R.; Shakibaei, G. I.; Bazgir, A. Monatsh. Chem. 2010, 141, 1077.
[10] Sanaeishoar, T.; Tavakkoli, H.; Mohave, F. Appl. Catal., A 2014, 470, 56.
[11] Shaabani, A.; Seyyedhamzeh, M.; Shaabani, S.; Ganji, N. Res. Chem. Intermed. 2015, 41, 2377.
[12] Azizi, N.; Dezfooli, S. Environ. Chem. Lett. 2015, 14, 201.
[13] Allahabadi, E.; Ebrahimi, S.; Soheilizad, M.; Khoshneviszadeh, M.; Mandavi, M. Tetrahedron Lett. 2016, 58, 121.
[14] Rostami, M. E.; Gorji, B.; Zadmard, R. Tetrahedron Lett. 2018, 59, 2393.
[15] Kurva, M.; Pharande, S. G.; Quezada-Soto, A.; Gamez-Montano, R. Tetrahedron Lett. 2018, 59, 1596.
[16] Chernyak, N.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2743.
[17] Reddy, B. V. S.; Reddy, P. S.; Reddy, Y. J. Tetrahedron Lett. 2011, 52, 5789.
[18] Zong, C.-L.; Zeng, R.-S.; Zou, J.-P. Chem. Res. Chin. Univ. 2014, 30, 632.
[19] Lu, J.; Li, X.-T.; Ma, E.-Q.; Mo, L.-P.; Zhang, Z.-H. ChemCatChem 2015, 46, 2854.
[20] Maleki, A. Helv. Chim. Acta 2014, 97, 587.
[21] Rassokhina, I. V.; Shirinian, V. Z.; Zavarzin, I. V.; Gevorgyan, V.; Volkova, Y. A. J. Org. Chem. 2015, 80, 11212.
[22] Balijapalli, U.; Iyer, S. K. Dyes Pigm. 2015, 121, 88.
[23] Mandlimath, T. R.; Sathiyanarayanan, K. I. RSC Adv. 2016, 6, 3117.
[24] Hussain, N.; Gogoi, P.; Das, M. R.; Sengupta, P.; Fedorov, V. E.; Asanov, I. P.; Kozlova, M. N.; Artemkina, S. B. Appl. Catal., A 2017, 542, 368.
[25] Venkatesham, R.; Manjula, A.; Rao, V. B. J. Heterocycl. Chem. 2011, 48, 942.
[26] Abdollahi-Alibeik, M.; Rezaeipoor-Anari, A. Catal. Sci. Technol. 2014, 4, 1151.
[27] Li, X.-Q. J. Chem. Res. 2012, 9, 525.
[28] Wen, L.-R.; Li, Z.-R.; Li, M.; Cao, H. Green Chem. 2012, 14, 707.
[29] Cao, H.; Liu, X.; Zhao, L.; Cen, J.-H.; Lin, J.-X.; Zhu, Q.-X.; Fu, M.-L. Org. Lett. 2014, 45, 146.
[30] Kundu, S.; Basu, B. RSC Adv. 2015, 46, 50178.
[31] Yan, H.; Yan, R.; Yang, S.; Gao, X.; Wang, Y.-L.; Huang, G.-S.; Liang, Y.-M. Chem.-Asian J. 2013, 7, 2028.
[32] Kamal, A.; Reddy, C. N.; Satyaveni, M.; Chandrasekhar, D.; Nanubolu, J. B.; Singarapu, K. K.; Maurya, R. A. Chem. Commun. 2015, 51, 10475.
[33] Rao, C.-Q.; Mai, S.-Y.; Song, Q.-L. Org. Lett. 2017, 19, 4726.
[34] Dheer, D.; Rawal, R. K.; Singh, V.; Sangwan, P. L.; Das, P.; Shankar, R. Tetrahedron 2017, 73, 4295.
[35] Ghosh, P.; Ganguly, B.; Kar, B.; Dwivedi, S.; Das, S. Synth. Commun. 2018, 48, 1076.
[36] Odell, L. R.; Nilsson, M. T.; Gising, J.; Lagerlund, O.; Muthas, D.; Nordqvist, A.; Karlen, A.; Larhed, M. Bioorg. Med. Chem. Lett. 2009, 19, 4790.
[37] Mert-Balci, F.; Conrad, J.; Beifuss, U. ARKIVOC 2012, 3, 243.
[38] Maiti, B.; Chanda, K.; Selvaraju, M.; Tseng, C.-C.; Sun, C.-M. ACS Comb. Sci. 2013, 15, 291.
[39] Yadav, L. D. S.; Awasthi, C. Carbohydr. Res. 2010, 345, 318.
[40] Zhang, H.-P.; Jiang, L.-L. Tetrahedron Lett. 2015, 56, 2777.
[41] Karamthulla, S.; Khan, M. N.; Choudhury, L. H. RSC Adv. 2015, 5, 19724.
[42] Wagare, D. S.; Farooqui, M.; Keche, T. D.; Durrani, A. Synth. Commun. 2016, 46, 1741.
[43] Rao, R. N.; Balamurali, M. M.; Maiti, B.; Thakuria, R.; Chanda, K. ACS Comb. Sci. 2018, 20, 164.
[44] Chen, J. J.; Golebiowski, A.; Mcclenaghan, J.; Klopfenstein, S. R.; West, L. Tetrahedron Lett. 2001, 42, 2269.
[45] Chen, Y.; Lam, Y. L.; Lai, Y.-H. Org. Lett. 2002, 4, 3935.
[46] Lyon, M. A.; Kercher, T. S. Org. Lett. 2004, 6, 4989.

咪唑并[1,2-a]吡啶化合物绿色合成的研究进展

Research Progress on Green Synthesis of Imidazo[1,2-a]pyridine Compounds

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