Chinese Journal of Organic Chemistry >
Research Progress on Green Synthesis of Imidazo[1,2-a]pyridine Compounds
Received date: 2018-09-27
Revised date: 2018-11-24
Online published: 2019-01-10
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.
Zhao Xinyu, Ding Yangyang, Lü Yingtao, Kang Congmin . Research Progress on Green Synthesis of Imidazo[1,2-a]pyridine Compounds[J]. Chinese Journal of Organic Chemistry, 2019 , 39(5) : 1304 -1315 . DOI: 10.6023/cjoc201809034
[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.
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