REVIEW

Latest Progress and Application of Mannich Reaction

  • Liu Yuting ,
  • Wu Qianqian ,
  • Yin Dawei ,
  • Li Diyang
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  • Key Laboratory of Auxiliary Chemistry & Technology for Chemical Industry, Ministry of Education, College of Chemistry and Chemical Engineering, Shaanxi University of Science & Technology, Xi'an 710021

Received date: 2015-11-13

  Revised date: 2015-12-15

  Online published: 2016-01-15

Supported by

Project supported by the Key Laboratory Project of Shaanxi Provincial Department of Education (No. 13J017) and the Preliminary Projects of National Basic Research Program of China (973 Program) (No. 2014CB260411).

Abstract

Mannich reaction is very important in organic chemistry, especially plays a very important role in the synthesis of drugs. In addition, Mannich base has widespread attention because of it is more significant and specific biological activity. Mannich reaction, diastereoselectivity Mannich reaction, enantioselective Mannich reaction and the application of Mannich reaction are introduced. Finally, the development aspect of this research is brought forward.

Cite this article

Liu Yuting , Wu Qianqian , Yin Dawei , Li Diyang . Latest Progress and Application of Mannich Reaction[J]. Chinese Journal of Organic Chemistry, 2016 , 36(5) : 927 -938 . DOI: 10.6023/cjoc201511024

References

[1] Sahoo, S.; Joseph, T.; Halligudi, S. B. J. Mol. Catal. A: Chem. 2006, 244, 179.
[2] Zhang, Y. W.; Wang, J. F.; Sheng Z. X. Chin. J. Org. Chem. 2003, 23, 1324 (in Chinese).
(张雅文, 王建非, 沈宗旋, 有机化学, 2003, 23, 1324.)
[3] Muller, R.; Goesmann, H.; Waldmann, H. Angew. Chem., Int. Ed. 1999, 38, 184.
[4] Toure, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439
[5] Arend, M.; Westermann, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1044
[6] Atsuto, I.; Kazuhiro, Y.; Akira, Y. Org. Lett. 2009, 11, 5310.
[7] Cordova, A.; Rios, R. Acc. Chem. Res. 2004, 37, 102.
[8] Dong, H. P.; Venkatesan, J.; Kim, S. K.; Ramkumar, V.; Parthiban, P. Bioorg. Med. Chem. Lett. 2012, 22, 6362.
[9] Gul, H. I.; Ojanen, T.; Vepsalainen, J.; Gul, M.; Erciyas, E.; Hanninen, O. Arzneim.-Forsch. 2001, 51, 72.
[10] Lopes, F.; Capela, R.; Goncaves, J. O.; Horton, P. N.; Hursthouse, M. B.; Iley, J.; Casimiro, C. M.; Bom, J.; Moreira, R. Tetrahedron Lett. 2004, 45, 7663.
[11] Ferlin, M. G.; Chiarelotto, G.; Antonucci, F.; Caparrotta, L.; Froldi, G. Eur. J. Med. Chem. 2002, 37, 427.
[12] Sheela, J.; Navita, K.; Prapti, T. Bioorg. Med. Chem. 2004, 12, 571.
[13] Malinka, W.; Swiatek, P.; Filipek, B.; Sapa, J.; Jezierska, A.; Koll, A. Farmaco2005, 60, 961.
[14] Xu, Q. G.; Liu, T.; Tian, R.; Ma, D. Y.; Li, Q. G. Chin. J. Org. Chem. 2008, 28, 234 (in Chinese).
(徐启贵, 刘天渝, 田睿, 马德银, 李勤耕, 有机化学, 2008, 28, 234.)
[15] Zhou, Z. W.; Yan, J. F.; Tang, X. M.; Zhang, W. Y.; Zhang, Y. X.; Chen, X.; Su, X. Y.; Yang, D. C. Chin. J. Org. Chem. 2010, 30, 582 (in Chinese).
(周祖文, 晏菊芳, 唐雪梅, 张蔚瑜, 张映霞, 陈欣, 苏小燕, 杨大成, 有机化学, 2010, 30, 582.)
[16] Wang, B.; Zhao, L. X.; Ji, Z. Z. Chin. Med. Chem. 2000, 10, 26 (in Chinese).
(王飚, 赵临襄, 计志忠, 中国药物化学杂志, 2000, 10, 26.)
[17] Yildirim, M.; Celike, D.; Durust, Y.; Knight, D. W.; Kariuki, B. M. Tetrahedron 2014, 70, 2122.
[18] Sun, X.; Hu, C. Q.; H, X. D.; Dong, J. C. Chin. J. Org. Chem. 2003, 23, 81 (in Chinese).
(孙逊, 胡昌奇, 黄晓东, 董纪昌, 有机化学, 2003, 23, 81.)
[19] Yue, C. B.; Yi, T. F.; Zhu, C. B.; Liu, G.. J. Ind. Eng. Chem. 2009, 15, 653.
[20] Yang, Z. P. M.S. Thesis, Shaanxi University of Science & Technology, Xi'an, 2012 (in Chinese).
(杨支朋. 硕士论文, 陕西科技大学, 西安, 2012.)
[21] Mou, L. Y.; Lin, Z. Y.; Zhu, L. Y.; Liang, X. T. Chin. J. Org. Chem. 2008, 28, 274 (in Chinese).
(牟丽媛, 林紫云, 朱莉亚, 梁晓天, 有机化学, 2008, 28, 274.)
[22] Pishawikar, S. A.; More, H. N. Arabian J. Chem. 2013, 48.
[23] Oloyede, G. K.; Willie, I. E.; Adeeko, O. O. Food Chem.2014, 165, 515.
[24] Wang, J. M.S. Thesis, Shaanxi University of Science & Technology, Xi'an, 2014 (in Chinese).
(王捷, 硕士论文, 陕西科技大学, 西安, 2014.)
[25] Zhao, M. T. M.S. Thesis, Shaanxi University of Science & Technology, Xi'an, 2012 (in Chinese).
(赵明涛, 硕士论文, 陕西科技大学, 西安, 2012.)
[26] Idhayadhulla, A.; Kumar, R. S.; Nasser, A. J. A.; Selvin, J.; Manilal, A. Arabian J. Chem. 2014, 7, 994.
[27] Sriram, D.; Yogeeswari, P.; Reddy, S. P. Bioorg. Med. Chem. Lett. 2006, 16, 2113.
[28] Urbaniak, M.; Iwanek, W. Tetrahedron 2006, 62, 1508.
[29] Chen, S. M.S. Thesis, Shaanxi University of Science &Technology, Xi'an, 2012 (in Chinese).
(陈澍, 硕士论文, 陕西科技大学, 西安, 2012.)
[30] Aeluri, R.; Alla, M.; Polepalli, S.; Jain, N.Eur. J. Med. Chem.2015, 100, 18.
[31] Sakharam, B. D.; Hemant, V. C.; Pravin, S. B.; Yoginath, B. M.; Amol, S. K.; Babasaheb, P. B. Chin. Chem. Lett. 2015.
[32] Barahman, M.; Leili, T.; Akbar, M. Tetrahedron Lett. 2015, 56, 1851.
[33] Liu, F. J.; Meng, X. J.; Zhang, Y. L.; Ren, L. M.; Nawaz, F.; Xiao, F. S. J. Catal. 2010, 271, 52.
[34] Mondal, J.; Sen, T.; Bhaumik, A. Dalton Trans. 2012, 41, 6173.
[35] Melero, J. A.; Bautista, L. F.; Morales, G.; Iglesias, J.; Briones, D.Energy Fuels 2009, 23, 539.
[36] Mbaraka, I. K.; Shanks, B. H. J. Catal. 2005, 229, 365.
[37] Molares, G.; Athens, G.; Chmelka, B. F.; Van, G. R.; Melero, J. A. J. Catal. 2008, 254, 205.
[38] Okuhara, T. Chem. Rev. 2002, 102, 3641
[39] Karimi, B.; Mirzaei, H. M.; Mobaraki, A. Catal.Sci. Technol. 2012, 2, 828.
[40] Karimi, B.; Mobaraki, A.; Mirzaei, H. M.; Zareyee, D.; Vali, H. Chem. Catal. Chem. 2014, 6, 212.
[41] Mobaraki, A.; Movassagh, B.; Karimi, B. Appl. Catal. A: Gen. 2014, 472, 123.
[42] Hui, Y. H.; Shi, W.; Xie, S. L.; Wang, C. C.; Xie, Z. F. Chin. J. Org. Chem. 2014, 34, 1212 (in Chinese).
(惠永海, 石伟, 谢绍雷, 王长春, 解正峰. 有机化学, 2014, 34, 1212.)
[43] Pham, K.; Huang, X.; Zhang, W. Tetrahedron Lett. 2015, 56, 1998.
[44] Zhang, C. L.; Wang, X.; Guo, Y.; Wu, Y. F.; Gao, L. N.; Sun, L. J.; Chai, J. H.; Zhu, C. A. Chin. J. Org. Chem. 2014, 34, 2331 (in Chinese).
(张成路, 王雪, 国阳, 吴一菲, 高丽娜, 孙丽杰, 柴金华, 朱长安, 有机化学, 2014, 34, 2331.)
[45] Liu, B. M.; Zhang, M. H.; Tao, S. J.; Xia, M. Y.; Dong, J. H. Chin. J. Med. Chem. 2014, 24, 271 (in Chinese).
(刘冰弥, 张美慧, 陶淑娟, 夏明钰, 董金华, 中国药物化学杂志, 2014, 24, 271.)
[46] Ma, J. B.; Zhai, F.; Qu, Q. Appl. Chem. Ind. 2013, 42, 1480 (in Chinese).
(麻纪斌, 翟帆, 曲秦, 应用化工, 2013, 42, 1480.)
[47] Yang, F.; Liu, A. L.; Du, G. H. Chin. J. Pharm. 2010, 45, 90 (in Chinese).
(杨帆, 刘艾林, 杜冠华, 中国药学杂志, 2010, 45, 90.)
[48] Zhao, X. J.; Cui, Z. H.; Wang, R. L.; Li, X.; Fan, S. J.; Chen, W. G. Chin. Chem. Lett. 2015, 26, 259.
[49] Chem, S. J.; Liu, X.; Hui, Y. N. Corros. Prot. 2007, 28, 646 (in Chinese).
(陈世军, 刘祥, 惠艳妮, 缓蚀与防护, 2007, 28, 646.)
[50] Shi, L.; W, C. F.; X, Y.; Wang, Q. A. Chin. J. Org. Chem. 2015, 35, 1537 (in Chinese).
(史玲, 王彩芳, 徐雨, 汪秋安, 有机化学, 2015, 35, 1537.)
[51] Zhang, W. F.; Lin, Q.; Lin, J. East Highway 2006, 2, 61 (in Chinese).
(张万烽, 林青, 林建, 华东公路, 2006, 2, 61.)
[52] Zhou, J. F.; Ji, S. P; Chuan, Y. M; Jiang, L.; Li, H. L.; Yuan, M. L. J. Yunnan Univ.(Nat. Sci. Ed.)2015, 37, 124 (in Chinese).
(周江峰, 季四平, 钏永明, 蒋琳, 李宏利, 袁明龙, 云南大学学报(自然科版), 2015, 37, 124.)
[53] Vladimir, P. P.; Dusica, S.; Sladjana, B. N.; Goran, A. B.; Svetlana, M.; Zorica, D. P. J. Mol. Struct. 2015, 1098, 34.
[54] Xia, J.; Qiu, R.; Yin, S.; Zhang, X. W.; Luo, S. L.; Au, C. T.; Xia, K.; Wong, W. Y. J. Organomet. Chem. 2010, 695, 1487.
[55] Kassaee, M. Z.; Mohammadi, R.; Masrouri, H.; Movahedi, F. Chin. Chem. Lett. 2011, 22, 1203.
[56] Li, Z. M.; Sun, Y.; Shen, X. M.; Ai, L.; Zhang, C. Chin. J. Org. Chem. 2006, 26, 465 (in Chinese).
(李志敏, 孙岩, 申秀民, 艾林, 张聪, 有机化学, 2006, 26, 465.)
[57] Wang, Y. Q.; Ren, Y. Y. Chin. J Catal. 2015, 36, 93.
[58] Chacko, S.; Ramapanicker, R. Tetrahedron Lett. 2015, 56, 2023.
[59] Mclean, N. J.; Heather, T.; Mark, W. Tetrahedron Lett. 2004, 45, 993.
[60] Reddy, S. R. S.; Reddy, B. R. P.; Reddy, P. V. G. Tetrahedron Lett. 2015, 56, 4984.
[61] Wu, Y. L.; Song, B. A.; Wang, Y. L. J. Chongqing Univ. 2003, 26, 68 (in Chinese).
(吴扬兰, 宋宝安, 王远亮, 重庆大学学报, 2003, 26, 68.)
[62] Guo, X.; Hu, W. H. Acc. Chem. Res. 2013, 46, 2427.
[63] Jiang, J.; Ma, X. C.; Liu, S. Y.; Qian, Y.; Lv, F. P.; Qiu, L.; Wu, X.; Hu, W. H. Chem. Commun. 2013, 49, 4238.

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