Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2702-2713.DOI: 10.6023/cjoc202003064 Previous Articles Next Articles
梁伟, 谭成侠, 翁建全, 刘幸海
收稿日期:
2020-03-29
修回日期:
2020-05-13
发布日期:
2020-06-01
通讯作者:
刘幸海
E-mail:xhliu@zjut.edu.cn
基金资助:
Liang Wei, Tan Chengxia, Weng Jianquan, Liu Xinghai
Received:
2020-03-29
Revised:
2020-05-13
Published:
2020-06-01
Supported by:
Share
Liang Wei, Tan Chengxia, Weng Jianquan, Liu Xinghai. Advances on Synthesis and Biological Activities of Mesoionic Compounds[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2702-2713.
[1] Earl, J. C.; Mackney, A. W. J. Chem. Soc. 1935, 899. [2] Huisgen, R.; Gotthardt, H.; Bayer, H, O. Angew. Chem., Int. Ed. 1964, 3, 136. [3] St Cyr, D. J.; Arndtsen, B. A. J. Am. Chem. Soc. 2007, 129, 12366. [4] Wilton, D. J.; Harrison, R. F.; Willett, P.; Delaney, J.; Lawson, K.; Mullier, G. J. Chem. Inf. Model. 2006, 46, 471. [5] Ollis, W. D.; Ramsden, C. A. Adv. Heterocycl. Chem. 1976, 19, 1. [6] Latthe, P. R.; Shinge, P. S.; Badami, B. V.; Patil, P. B.; Holihosur, S. N. J. Chem. Sci. 2006, 118, 249. [7] Gotthard, H.; Huisgen, R.; Schaefer, F. C. Tetrahedron Lett. 1964, 10, 487. [8] Zhang, W. M.; Holyoke, C. W.; Barry, J.; Leighty, R. M.; Cordova, D.; Vincent, D. R.; Briddell, T. A. Bioorg. Med. Chem. Lett. 2016, 26, 5444. [9] Zhang, W. M. Acc. Chem. Res. 2017, 50, 2381 [10] Holyoke, C. W. Jr.; Cordova, D.; Zhang, W. M.; Barry, D. J.; Leighty, M. R.; Dietrich, F. R.; Rauh, J. J.; Pahutski, F. T. Jr.; Lahm, P. G.; Tong, T. M.-H.; Benner, A. E.; Andreassi, L. J.; Smith, M. R.; Vincent, R. D.; Christianson, A. L.; Teixeira, A. L.; Singh, V.; Hughes, A. K. Pest Manage. Sci. 2017, 73, 796. [11] Coburn, R. A.; Carapellotti, R. A. J. Pharm. Sci. 1976, 65, 1505. [12] White, E. H.; Egger, N. J. Am. Chem. Soc. 1984, 106, 3701. [13] Chandrasekhar, R.; Nanjan, M. J. Mini. Rev. Med. Chem. 2012, 12, 1359. [14] Jogul, J. J.; Badami, B. V. J. Serb. Chem. Soc. 2006, 71, 851. [15] Kennis, L. E. J.; Bischoff, F. P.; Mertens, C. J.; Love, C. J.; Keybus, F. A. F. V.; Pieters, S.; Braeken, M.; Megens, A. A. H. P.; Leysen, J. E. Bioorg. Med. Chem. Lett. 2000, 10, 71. [16] Holyoke Jr, C. W.; Zhang, W. M.; Pahutski, T. F. Jr.; Lahm, G. P.; Tong, M. H. T.; Cordova, D.; Leighty, R. M. 13th IUPAC International Congress of Pesticide Chemistry——Discovery and Synthesis of Crop Protection Products, American Chemical Society, Washington, DC, USA, 2015, pp. 365~378. [17] Moustafa, M. A.; Gineinah, M. M.; Nasr, M. N.; Bayoumi, W. A. Arch. Pharm. Med. Chem. 2004, 337, 427. [18] Latthe, P. R.; Shinge, P. S.; Badami, B. V.; Patil, P. B.; Holihosur, S. N. J. Chem. Sci. 2006, 118, 249. [19] Taj, T.; Kamble, R. R.; Gireesh, T. M.; Hunnur, R. K. J. Serb. Chem. Soc. 2011, 76, 1069. [20] Patel, K. C.; Patel, H. D. E.-J. Chem. 2011, 8, 113. [21] Hegde, J. C.; Girish, K. S.; Adhikari, A.; Kalluraya, B. Synth. Commun. 2013, 43, 301. [22] Dubey, R.; Chaudhary, N.; Kumar, R.; Panwar, H. Orient. J. Chem. 2014, 30, 271. [23] Bayer, H. O.; Huisgen, R.; Knorr, R.; Schaefer, F. C. Chem. Ber. 1970, 103, 2581. [24] Potts, K.; Yao, S. J. Org. Chem. 1979, 44, 977 [25] Anderson, A. K.; Heider, A. R. Synth. Commun. 1986, 16, 357. [26] Kato, H.; Tani, K.; Kurumisawa, H.; Tamura, Y. Chem. Lett. 1980, 717. [27] Lu, Y.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2008, 47, 5430 [28] (a) Arndtsen, B. A. Chem.-Eur. J. 2009, 15, 302. (b) Quesenel, J. S.; Amdtsen, B. A. Pure. Appl. Chem. 2013, 85, 377. [29] Miao, Q.; Sun, H. L. Chin. Sci. Bull. 2015, 60, 2003(in Chinese). (苗群, 孙怀林, 科学通报, 2015, 60, 2003.) [30] Miao, Q. M.S. Thesis, Nankai University, Tianjin, 2015(in Chinese). (苗群, 硕士论文, 南开大学, 天津, 2015.) [31] Torres, G. M.; Quesnel, J. S.; Bijou, D.; Arndtsen, B. A. J. Am. Chem. Soc. 2016, 138, 7315. [32] St Cyr, D. J.; Arndtsen, B. A. J. Am. Chem. Soc. 2007, 129, 12366. [33] Couture, A.; Deniau, E.; Grandclaudon, P. Synthesis 1994, 953. [34] Morin, M. S. T.; St Cyr, D. J.; Arndtsen, B. A. Org. Lett. 2010, 12, 4916. [35] Morin, M. S. T.; Aly, S.; Arndtsen, B. A. Chem Commun. 2013, 49, 883. [36] Jeanmart, S.; Edmunds, A. F.; Lamberth, C. Bioorg. Med. Chem. 2016, 24, 317. [37] Holyoke, C. W.; Tong, M. T.; Coats, R. A. WO 099929, 2009. [38] Lugan, N.; Lavigne, G.; Labande, A.; Cesar, V. Organometallics 2014, 33, 5085. [39] Zhang, W. M.; Holyoke, W. C. Jr.; Pahutski, F. T. Jr.; Lahm, P. G.; Barry, D. J.; Cordova, D.; Leighty, M. R.; Singh, V.; Vincent, R. D.; Tong, T. M.-H.; Hughes, A. K.; Mc Cann, F. S.; Henry, T. Y.; Xu, M.; Briddell, A. T. Bioorg. Med. Chem. Lett. 2017, 27, 16. [40] Lei, G. Y.; Ying, J. W.; Song, Y. Q. Mod. Agrochem. 2017, 16, 14(in Chinese). (雷月光, 英君伍, 宋玉泉, 现代农药, 2017, 16, 14.) [41] Zhang, W. M.; Holyoke, W. C. Jr.; Barry, J.; Cordova, D.; Leighty, M. R.; Tong, T. M.-H.; Hughes, A. K.; Lahm, P. G.; Pahutski, F. T. Jr.; Xu, M.; Briddell, A. T.; Mc Cann, F. T.; Henry, T. Y.; Chen, Y. Z. Bioorg. Med. Chem. Lett. 2017, 27, 911. [42] (a) Liu, D. Y.; Zhang, J.; Zhao,.L; He, W. J.; Liu, Z. J.; Gan, X. H.; Song, B. A. J. Agric. Food Chem. 2019, 67, 11860. (b) Pan, J. K. M.S. Thesis, Guizhou University, Guiyang, 2017 (in Chinese). (潘建科, 硕士论文, 贵州大学, 贵阳, 2017.) [43] Hasegawa, S.; Kamo, T.; Kagohara, Y.; Miyake, T.; Kobayashi, T.; Matsuda, R.; Asano, S.; Kudamatsu, A. WO 171053, 2016. [44] Thieme, P.; Patsch, M.; Konig, H. Liebigs Ann. Chem. 1972, 764, 94. [45] Zhang, Z. Y.; Zhu, C. H.; Sun, X. W. Chem. J. Chin. Univ. 2000, 21, 386(in Chinese). (张自义, 褚长虎, 孙小文, 高等学校化学学报, 2000, 21, 386.) [46] Abbott, P. A.; Bonnert, R. V.; Caffrey, M. V.; Cage, P. A.; Cooke, A. J.; Furber, M.; Hill, S.; Withnall, J. Tetrahedron 2002, 58, 3185. [47] Avalos, M.; Babiano, R.; Cabanillas, A.; Cintas, P.; Higes, F. J.; Jiménez, J. L.; Palacios, J. C. J. Org. Chem. 1996, 61, 3738. [48] Arévalo, M. J.; Avalos, M.; Babiano, R.; Cintas, P.; Hursthouse, M. B.; Jiménez, J. L.; Light, M. E.; Palacios, J. C. Tetrahedron:Asymmetry 2002, 13, 223. [49] Avalos, M.; Babiano, R.; Cintas, P; Jimexnez, J. L.; Palacios, J. C. Acc. Chem. Res. 2005, 38, 460. [50] Chernyshev, V. N.; Astakhov, A. V.; Starikova, Z. A. Tetrahedron 2010, 66, 3301. [51] Hassan, A. A.; Bräse. S.; Tawfeek, H. N.; Mohamed, N. K.; Nieger, M.; El-Shaieb, K. M. A. Tetrahedron Lett. 2014, 55, 2385. [52] Zhao, S. X.; Yu, R. C.; Chen, W. Z.; Liu, M. C.; Wu, H. Y. Org. Lett. 2015, 17, 2828. [53] Erguven, H.; Leitch, D. C.; Keyzer, E. N.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2017, 56, 6078. [54] Samarskaya, A. S.; Cherepanov, I. A.; Godovikov, I. A.; Dmitrienko, A. O.; Moiseev, S. K.; Kalinin, V. N.; Hey-Hawkins, E. Tetrahedron 2018, 74, 2693. [55] Eilertsen, M.; Allin, S. M.; Pearson, R. J. Bioorg. Med. Chem. Lett. 2018, 28, 1106. [56] (a) He, W. J.; Liu, D. Y.; Gan, X. H.; Zhang, J.; Liu, Z. J.; Yi, C. F.; Song, B. A. Chin. J. Org. Chem. 2019, 39, 2287(in Chinese). (何文静, 刘登曰, 甘秀海, 张建, 刘峥军, 易崇粉, 宋宝安, 有机化学, 2019, 39, 2287.) (b) He, W. J. M.S. Thesis, Guizhou University, Guiyang, 2019 (in Chinese). (何文静, 硕士论文, 贵州大学, 贵阳, 2019.) [57] Kuzmina, O. M.; Weisel, M.; Narine, A. A. Eur. J. Org. Chem. 2019, 5527. [58] Benaissa, A.; Pallova, L.; Morantin, M. E.; Lafitte, T.; Huynh, M.; Barthes, C.; Vendier, L.; Lugan, N.; Bastin, S.; César, V. Chem.-Eur. J. 2019, 3, 242. [59] Hansmann, M. M.; Antoni, P. W.; Pescht, H. Angew. Chem., Int. Ed. 2020, 59, 2. [60] Narine, A.; Dickhaut, J.; Kaiser, F.; Bandur, N. G.; Koerber, K.; Von Deyn, W.; Derksen, S.; Paulini, R.; Culbertson, D. L. WO 144228, 2013. [61] Dickhaut, J.; Narine, A.; Derksen, S.; Bandur, N. G.; Von Deyn, W.; Koller, R.; Wach, J. Y.; Langewald, J.; Rankl, N. B. WO 202582, 2014. [62] Narine, A.; Bandur, N. G.; Dickhaut, J.; Derksen, S.; Koller, R.; Von Deyn, W.; Wach, J.-Y.; Culbertson, D. L. WO 167084, 2014. [63] Narine, A.; Dickhaut, J.; Kaiser, F.; Bandur, N. G.; Koerber, K.; Von Deyn, W. WO 033244, 2014. [64] Dickhaut, J.; Narine, A.; Von Deyn, W.; Koller, R.; Wach, J.-Y.; Vyas, D.; Adisechan, A.; Shinde, H. WO 055431, 2016. [65] Markus, H.; Daniela, P.; Kerstin, I.; Ulrich, G.; Silvia, C. G.; Marc, M.; Sascha, E.; Andreas, T. WO 093214, 2018. [66] Heil, M.; Hoffmeister, L.; Webber, M.; Ilg, K.; Goergens, U.; Turberg, A. WO 192872, 2018. [67] Holyoke, W. C. Jr. WO 208595, 2018. |
[1] | Luo Chunyan, Ma Wenjing, Lv Liang, Pang Huailin, Xiang Juncheng, Zhou Liqi, Yin Dulin, Liu Jiyong. Synthesis and Insecticidal Activity of Novel meta-Diamide Compounds Containing Cyclopropyl Group [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2963-2970. |
[2] | Kong Yaolei, Sun Xiaotong, Weng Jianquan. Selectfluor as “Fluorine-Free” Functional Reagent Applied to Organic Synthesis under Transition Metal-Free Conditions [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2641-2657. |
[3] | Zhang Zhu, Li Jiazhu, Wang Xinyue, Ma Jihua, Wang Xu, Wang Jinjun. Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2895-2903. |
[4] | Zhang Jingpeng, Yang Zhaokai, Qin Yaoguo, Yang Xinling. Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing 1,2,3-Thiadiazole [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2971-2979. |
[5] | Zhang Luye, Zhang Yang, Wang Zhengjie, Wang Tao, Li Erdong, Liu Limin, Liu Xiujuan, Zheng Jiaxin, Ke Yu, Shan Lihong, Liu Hongmin, Zhang Qiurong. Synthesis and Antitumor Activity of Novel Quinazoline Derivatives Containing Acrylamide [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2804-2810. |
[6] | Lei Kang, Li Pan, Zhou Xiaoyun, Wang Shiben, Wang Xuekun, Ji Lusha, Liu Renmin, Xu Xiaohua. Design, Synthesis and Herbicidal Activity of 5-Acylbarbituric Acid Derivatives and Study of Molecular Mode of Action [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2788-2797. |
[7] | Pan Chao, Liu Peng, Wu An'guo, Li Ming, Wen Lirong, Guo Weisi. Electrochemical-Promoted Synthesis of 2-Thiazolines via Selenylation/Cyclization of N-Allylthioamides [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2855-2862. |
[8] | Li Fangyao, Huang Lin, Zhou Xiaoqun, Li Qian, Ma Xianli, Duan Wengui, Wang Xiu. Synthesis and Cytotoxicity Evaluation of Dehydroabietic Acid Derivatives Bearing Nitrate Moiety [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2845-2854. |
[9] | Jiang Zhenhua, Cheng Yi'nan, Shen Guofu, Zhang Mengmeng, Su Ziyang, Sun Liansheng, Li Honglian. Synthesis of 1,2,4-Triazole Benzamide Derivatives and Fungicidal Activity [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2575-2582. |
[10] | He Mei, He Chaofan, Liu Ling, Ye Jiao, Hu Aixi, Chen Yun, Xu Lujie, Liu Ailin. Synthesis, Crystal Structure and Neuraminidase Inhibitory Activity of 1,2,4-Triazole-3-sulfide Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2402-2410. |
[11] | Tang Xianjun, Lu Xingliang, Yang Dan, Zhang Min, Xiong Yongtong, Wu Qinglai, Li Junkai. Synthesis and Fungicidal Activities of Novel Tertiary Alcohol Ergosterol Biosynthesis Inhibitors Based on Phenazine-1-carboxylic Acid [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2491-2501. |
[12] | Zhao Yu, Liu Xinlei, Li Yihao, Xu Leichuan, Su Yanhao, Jiang Jiazhen, Wang Ming'an. Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2547-2554. |
[13] | Zeng Hongyun, Zhang Jun'gan, Hong Wei. New Method for the Synthesis of 2,5-Diaryl Substituted Thiazoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2535-2542. |
[14] | Liu Jingjing, Zhang Donghui, Jiang Weinan, Liu Runhui. Simple and Cost-Effective Synthesis of Fmoc-DOPA(acetonide)-OH [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2543-2546. |
[15] | Li Qianqian, Wu Zhongmei, Zhang Min, Zhang Yiping, Zhou Yingkai, Deng Hongmei, Song Liping. Synthesis and Preliminary Exploration of Biological Activity of 3-Aryl-4-arylamine Methyl Isoxazoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2108-2113. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||