综述与进展

多组分反应在合成多取代咪唑类化合物中的应用

  • 肖立伟 ,
  • 彭晓霞 ,
  • 周秋香 ,
  • 寇伟 ,
  • 时亚茹
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  • 廊坊师范学院 化学与材料科学学院 廊坊 065000

收稿日期: 2014-12-05

  修回日期: 2015-02-09

  网络出版日期: 2015-02-11

基金资助

河北省自然科学基金(No. B2013408014)和廊坊师范学院重点(No. LSLZ201402)资助项目.

Application of Multi-component Reaction in Synthesis of Multi- substituted Imidazoles

  • Xiao Liwei ,
  • Peng Xiaoxia ,
  • Zhou Qiuxiang ,
  • Kou Wei ,
  • Shi Yaru
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  • Faculty of Chemistry and Material Science, Langfang Teachers University, Langfang 065000

Received date: 2014-12-05

  Revised date: 2015-02-09

  Online published: 2015-02-11

Supported by

Project supported by the Natural Science Foundation of Hebei Province (No. B2013408014) and the Key Foundation of Langfang Teachers University (No. LSLZ201402).

摘要

多取代咪唑类化合物包括三取代咪唑和四取代咪唑, 在医药、化学传感及催化等领域有重要应用. 多组分反应作为原子经济性和反应选择性很高的一类反应, 广泛应用于多取代咪唑的合成中. 基于反应原料及方法进行分类, 综述了近年来利用多组分反应合成多取代咪唑类化合物的研究进展情况.

本文引用格式

肖立伟 , 彭晓霞 , 周秋香 , 寇伟 , 时亚茹 . 多组分反应在合成多取代咪唑类化合物中的应用[J]. 有机化学, 2015 , 35(6) : 1204 -1215 . DOI: 10.6023/cjoc201412012

Abstract

Multi substituted imidazoles including tri- and tetra-substituted imidazoles, play important roles in the field of pharmaceutical, chemical sensing and catalysis etc. Multi-component reaction (MCR), a protocol with high atom economic and reaction selectivity, has been applied widly on the synthesis of multi-substituted imidazoles. Based on different starting materials and different methods, the recent advances in the synthesis of multi-substituted imidazols via multi-component reaction are reviewed.

参考文献

[1] Koch, P.; Bauerlein, C.; Jank, H.; Laufer, S. J. Med. Chem. 2008, 51, 5630.
[2] Li, W. J.; Li, Q.; Liu, D. L.; Ding, M. W. J. Agric. Food Chem. 2013, 61, 1419.
[3] Xu, Z. X.; Wang, S. M.; Zhao, L.; Zhang, S. L.; Li, J. B. Chin. J. Org. Chem. 2003, 23(9), 950 (in Chinese). (许祖勋, 王世敏, 赵雷, 张胜利, 黎俊波, 有机化学, 2003, 23(9), 950.)
[4] Yang, W. H.; Xiao, G. M.; Kong, X. X. Appl. Chem. 2003, 20(4), 406 (in Chinese). (杨为华, 肖国民, 孔祥翔, 应用化学, 2003, 20(4), 406.)
[5] Dupont, J.; de Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
[6] Ye, H.; Wang, W.; Zhu, X.; Chen, W.; Xie, L.; Yuan, Y. Chin. J. Org. Chem. 2013, 33, 827 (in Chinese). (叶宏民, 王薇, 朱晓晓, 陈伟强, 谢莉莉, 袁耀锋, 有机化学, 2013, 33, 827.)
[7] Bian, L.; Zeng, X.; He, R.; Luo, C.; Lin, Z. Chin. J. Org. Chem. 2014, 34, 994 (in Chinese). (卞垒, 曾向潮, 何如, 罗创龙, 林志强, 有机化学, 2014, 34, 994.)
[8] Gao, X.; Fan, J.; Wang, X.; Zhang, Y. Acta Chim. Sinica 2013, 71, 1411 (in Chinese). (高霞, 樊静, 王小龙 张艳树, 化学学报, 2013, 71, 1411.)
[9] Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
[10] Climent, M. J.; Corma, A.; Iborra, S. RSC Adv. 2012, 2, 16.
[11] Domling, A. Chem. Rev. 2006, 106, 17.
[12] Cao, S.; Jing, Y.; Liu, Y.; Wan, J. Chin. J. Org. Chem. 2014, 34, 876 (in Chinese). (曹硕, 景艳锋, 刘云云, 万结平, 有机化学, 2014, 34, 876.)
[13] Tang, M.; Xing, D.; Cai, M.; Hu, W. Chin. J. Org. Chem. 2014, 34, 1268 (in Chinese). (唐敏, 邢栋, 蔡茂强, 胡文浩, 有机化学, 2014, 34 , 1268.)
[14] Radziszewski, B. Chem. Ber. 1882, 15, 1493.
[15] Japp, F.; Robinson, H. Chem. Ber. 1882, 15, 1268.
[16] Karimi-Jaberi, Z.; Barekat, M. Chin. Chem. Lett. 2010, 21(10), 1183.
[17] Joshi, R. S.; Mandhane, P. G.; Shaikh, M. U.; Kale, R. P.; Gill, C. H. Chin. Chem. Lett. 2010, 21(4), 429.
[18] Pasha, M. A.; Nizam, A. J. Saudi Chem. Soc. 2011, 15(1), 55
[19] Das, B.; Kashanna, J.; Kumar, R. A.; Jangili, P. Monatsh. Chem. 2013, 144 (2), 223.
[20] Sharma, S. D.; Hazarika, P.; Konwar, D. Tetrahedron Lett. 2008, 49(14), 2216.
[21] Reddy, M. V.; Jeong, Y. T. J. Fluorine Chem. 2012, 142, 45.
[22] Khosropour, A. R. Ultrason. Sonochem. 2008, 15(5), 659.
[23] Sangshetti, J. N.; Kokare, N. D.; Kotharkar, S. A.; Shinde, D. B. Chin. Chem. Lett. 2008, 19,762.
[24] Wang, L.-M.; Wang, Y.-H.; Tian, H.; Yao, Y.-F.; Shao, J.-H.; Liu, B. J. Fluorine Chem. 2006, 127(12), 1570.
[25] Shen, M.-G.; Cai, C.; Yi, W.-B. J. Fluorine Chem. 2008, 129(6), 541
[26] Karami, B.; Dehghani, F. M.; Eskandari, K. Croat. Chem. Acta 2012, 85(2), 147.
[27] Rajanarendar, E.; Murthy, K. R.; Reddy, M. N. Indian J. Chem. 2011, 50B, 926
[28] Kidwai, M.; Mothsra, P.; Bansal, V.; Somvanshi, R. K.; Ethayathulla, A. S.; Dey, S.; Singh, T. P. J. Mol. Catal. A: Chem. 2007, 265(1~2), 177.
[29] Wang, X. C.; Gong, H. P.; Quan, Z. J.; Li, L.; Ye, H. L. Chin. Chem. Lett. 2009, 20(1), 44
[30] Chary, M. V.; Keerthysri, N. C.; Vupallapati, S. V. N.; Lingaiah, N.; Kantevari, S. Catal. Commun. 2008, 9(10), 2013.
[31] Murthy, S. N.; Madhav, B.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51(40), 5252.
[32] Ramesh, K.; Murthy, S. N.; Karnakar, K.; Nageswar, Y. V. D.; Vijayalakhshmi, K.; Devi, B. L. A. P.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53(9), 1126.
[33] Samai, S.; Nandi, G. C.; Singh, P.; Singh, M.S. Tetrahedron 2009, 65(49), 10155.
[34] Nagargoje, D.; Mandhane, P.; Shingote, S.; Badadhe, P.; Gill, C. Ultrason. Sonochem. 2012 19, 94.
[35] Mahajan, A.; Aulakh, R. K.; Bedi , R. K.; Kumar, S.; Kumar, S.; Aswal, D. K. Synth. Met. 2012, 162, 58.
[36] Martorana, A.; Pace, A.; Buscemi, S.; Piccionello, A. P. Org. Lett. 2012, 14(13), 3240.
[37] Xue, W.-J.; Li, H.-Z.; Gao, F.-F.; Wu, A. Tetrahedron 2014, 70(2), 239.
[38] Zang, H.; Su, Q.; Mo, Y.; Cheng, B.-W.; Jun, S. Ultrason. Sonochem. 2010, 17(5), 749.
[39] Siddiqui, S. A.; Narkhede, U. C.; Palimkar, S. S.; Daniel, T.; Lahoti, R. J.; Srinivasan K. V. Tetrahedron 2005, 61(14), 3539.
[40] Xia, M.; Lu, Y.-D. J. Mol. Catal. A: Chem. 2007, 265(1~2), 205.
[41] Shaterian, H. R.; Ranjbar, M. J. Mol. Liq. 2011, 160 (1), 40.
[42] Zolfigol, M. A.; Khazaei, A.; Moosavi-Zare, A. R.; Zare, A.; Asgari, Z.; Khakyzadeh, V.; Hasaninejad, A. J. Ind. Eng. Chem. 2013, 19(3), 721.
[43] MaGee, D. I.; Bahramnejad, M.; Dabiri, M. Tetrahedron Lett. 2013, 54(21), 2591.
[44] Jourshari, M. S.; Mamaghani, M.; Shirini, F.; Tabatabaeian, K.; Rassa, M.; Langari, H. Chin. Chem. Lett. 2013, 24(11), 993.
[45] Heravi, M. M.; Derikvand, F.; Bamoharram, F. F. J Mol. Catal. A: Chem. 2007, 263(1~2), 112.
[46] Nagarapu, L.; Apuri, S.; Kantevari, S. J Mol. Catal. A: Chem. 2007, 266(1~2), 104.
[47] Fantini, M.; Zuliani, V.; Spotti, M. A.; Rivara, M. J. Comb. Chem. 2010, 12(1), 181.
[48] Heravi, M. M.; Bakhtiari, K.; Oskooie, H. A.; Taheri, S. J. Mol. Catal. A: Chem. 2007, 263(1~2), 279.
[49] Kannan, V.; Sreekumar, K. J. Mol. Catal. A: Chem. 2013, 376, 34.
[50] Kantevari, S.; Vuppalapati, S. V. N.; Biradar, D. O.; Nagarapu. L. J. Mol. Catal. A: Chem. 2007, 266(1~2), 109.
[51] Karimi, A. R.; Alimohammadi, Z.; Azizian, J.; Mohammadi, A. A.; Mohammadizadeh, M. R. Catal. Commun. 2006, 7(9), 728.
[52] Niknam, K.; Deris, A.; Naeimi, F.; Majleci, F. Tetrahedron Lett. 2011, 52(36), 4642.
[53] Mukhopadhyay, C.; Tapaswi, P. K.; Drew, M. G. B. Tetrahedron Lett. 2010, 51(30), 3944.
[54] Sivakumar, K.; Kathirvel, A.; Lalitha, A. Tetrahedron Lett. 2010, 51(22), 3018.
[55] Gupta, P.; Paul, S. J. Mol. Catal. A: Chem. 2012, 352, 75
[56] Mohammadi, A.; Keshvari, H.; Sandaroos, R.; Maleki, B.; Rouhi, H.; Moradi, H.; Sepehr, Z.; Damavandi, S. Appl. Catal., A: Gen. 2012, 429430, 73.
[57] Mekheimer, R. A.; Hameed, A. M. A.; Mansour, S. A. A.; Sadek, K. U. Chin. Chem. Lett. 2009, 20(7), 812.
[58] Xiao, L. W.; Gao, H. J.; Kong, J.; Liu, G. X.; Li, L. L.; Duan, J. D. Chin. J. Org. Chem. 2014, 34(12), 2511 (in Chinese). (肖立伟, 高红杰, 孔洁, 刘光仙, 李玲玲, 段敬丹, 有机化学, 2014, 34(12), 2511.)
[59] Safari, J.; Zarnegar, Z. C. R. Chim. 2013, 16(10), 920.
[60] Safari, J.; Zarnegar, Z. Ultrason. Sonochem. 2013, 20(2), 740.
[61] Safari, J.; Gandomi-Ravandi, S.; Akbari, Z. J. Adv. Res., 2013, 4(6), 509.
[62] Teimouri, A.; Chermahini, A. N. J. Mol. Catal. A: Chem. 2011, 346(1~2), 39.
[63] Ray, S.; Das, P.; Bhaumik, A.; Dutta, A.; Mukhopadhyay, C. Appl. Catal., A: Gen. 2013, 458, 183.
[64] Keivanloo, A.; Bakherad, M.; Imanifar, E.; Mirzaee, M. Appl. Catal., A: Gen. 2013, 467, 291.
[65] Mirjalili, B. F.; Bamoniri, A. H.; Zamani, L. Sci. Iran. 2012, 19(3), 565.
[66] Aziizi, N.; Manochehri, Z.; Nahayi, A.; Torkashvand, S. J. Mol. Liq. 2014, 196, 153.
[67] Rostamnia, S.; Zabardasti, A. J. Fluorine Chem. 2012, 144, 69.
[68] Rajaguru, K.; Suresh, R.; Mariappan, A.; Muthusubramanian, S.; Bhuvanesh, N. Org. Lett. 2014, 16(3), 744.
[69] Pandya, A. N.; Agrawal, D. K. Tetrahedron Lett. 2014, 55(10), 1835.
[70] Mamedov, V. A.; Zhukova, N. A.; Beschastnova, T. N.; Gubaidullin, A. T.; Rakov, D. V.; Rizvanov, I. K. Tetrahedron Lett. 2011, 52(33), 4280.
[71] Li, B.; Gu, Q.; He, Y.; Zhao, T.; Wang, S.; Kang, J.; Zhang, Y. C. R. Chim. 2012, 15(9), 784.
[72] Mlostoń, G.; Obijalska, E.; Heimgartner, H. J. Fluorine Chem. 2011, 132(11), 951.
[73] Liu, X.; Wang, D.; Chen, B. Tetrahedron 2013, 69(45), 9417.
[74] Tang, D.; Wu, P.; Liu, X.; Chen, Y.-X.; Guo, S.-B.; Chen, W.-L.; Li, J.-G.; Chen, B.-H. J. Org. Chem. 2013, 78(6), 2746.
[75] Guo, C.; Zhang, C.; Li, X.; Li, W.; Xu, Z.; Bao, L.; Ding, Y.; Wang, L.; Li, S. Bioorg. Med. Chem. Lett. 2013, 23(21), 5850.
[76] Pusch, S.; Opatz, T. Org. Lett. 2014, 16, 5430.
[77] Mehdi, A.; Samira, A.; Shahzad, F.; Jafar, A. D.; Peiman, M. Synlett 2009, 3263.
[78] Siamaki, A. R.; Arndtsen, B. A. J. Am. Chem. Soc. 2006, 128, 6050.
[79] Jiang, Z; Lu, P.; Wang, Y. Org. Lett. 2012, 14(24), 6266.
[80] Chen, C.-Y.; Hu, W.-P.; Yan, P.-C.; Senadi, G. C.; Wang, J.-J. Org. Lett. 2013, 15(24), 6116.

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