Citation: Fu Liyan, Ji Baoming, Du Chenxia. Synthesis of a New Class of Chiral Maleimide Derivatives with C₂-Symmetry[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2685-2689. doi: 10.6023/cjoc201703001 shu

Synthesis of a New Class of Chiral Maleimide Derivatives with C₂-Symmetry

Fu Liyan ^a,b ,
Ji Baoming ^a,, ,
Du Chenxia ^b

a.
College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022
b.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Corresponding author: Ji Baoming, lyhxxjbm@126.com
Received Date: 1 March 2017
Revised Date: 7 June 2017
Available Online: 23 October 2017
Fund Project: the National Natural Science Foundation of China 21372112Project supported by the National Natural Science Foundation of China (No. 21372112)

Figures(2)

Starting from the readily available maleic anhydride and (R)-1, 1'-bi-2-naphthol (BINOL), an efficient method for the synthesis of a new class of chiral maleimide derivatives with C₂-symmetry was described, involving Williamson ether synthesis, Suzuki coupling reaction and deprotection reaction by microwave to give 3, 4-[(R)-3, 3'-diaryl-1, 1'-binaphthyl-2, 2'-dioxy]-maleimides in 6.2%~16% yields. Moreover, the structures of the target compound and key intermediates were confirmed by ¹H NMR, ¹³C NMR, HRMS and IR techniques.
- imide,
- BINOL,
- organic synthesis,
- chirality
1. [1]
  Hu, Y.-F. In Modern Organic Synthesis Reagents, Vol. 4, Chemical Industry Press, Beijing, 2011, p. 97 (in Chinese).
2. [2]
  Pu, L. Chem. Rev. 1998, 98, 2405. doi: 10.1021/cr970463w
3. [3]
  Gao, Y.-J.; Yang, L.-H.; Song, S.-J.; Ma, J.-J.; Tang, R.-X.; Bian, R.-H.; Liu, H.-Y.; Wu, Q.-H.; Wang, C. Chin. J. Org. Chem. 2008, 28, 8(in Chinese).
4. [4]
  Chen, Y. Y.; Jiang, Y. J.; Fan, Y. S.; Sha, D.; Wang, Q. F.; Zhang, G.; Zheng, L.; Zhang, S. Tetrahedron:Asymmetry 2012, 23, 904. doi: 10.1016/j.tetasy.2012.06.008
5. [5]
  Xu, S.; Wang, Z.; Zhang, X.; Ding, K. Eur. J. Org. Chem. 2011, 110.
6. [6]
  Xu, S.; Wang, Z.; Li, Y.; Zhang, X.; Wang, H.; Ding, K. Chem.-Eur. J. 2010, 16, 3021. doi: 10.1002/chem.v16:10
7. [7]
  Sengoku, T.; Murata, Y.; Aso. Y.; Kawakami, A.; Inuzuka, T.; Sakamoto, M.; Takahashi, M.; Yoda, H. Org. Lett. 2015, 17, 5846. doi: 10.1021/acs.orglett.5b03021
8. [8]
  Marminon, C.; Pierre, A.; Pfeiffer, B.; Perez, V.; Leonce, S.; Renard, P.; Prudhomme, M. Bioorg. Med. Chem. 2003, 11, 679. doi: 10.1016/S0968-0896(02)00532-1
9. [9]
  Wang, K.; Yan, Z.; Wang, N.; Liu, Z. Z. Chin. Chem. Lett. 2012, 23, 462. doi: 10.1016/j.cclet.2012.01.033
10. [10]
  Rigby, J. H.; Mateo, M. E. J. Am. Chem. Soc. 1997, 119, 12655. doi: 10.1021/ja972950z
11. [11]
  Rigby, J. H.; Maharoof, U. S. M.; Meteo, M. E. J. Am. Chem. Soc. 2000, 122, 6624. doi: 10.1021/ja000930i
12. [12]
  Awuah, E.; Capretta, A. J. Org. Chem. 2011, 76, 3122. doi: 10.1021/jo1025805
13. [13]
  Chung, J. Y. L.; Cai, C.; McMilliams, J. C.; Reamer, B. A.; Peter, G. D.; Cvetovich, R. J. J. Org. Chem. 2005, 70, 10342. doi: 10.1021/jo0514927
14. [14]
  Bartlett, S.; Nelson, A.; Org. Biomol. Chem. 2004, 2, 2874. doi: 10.1039/b405010j
15. [15]
  Shen, L.; Prouty, C.; Conway, B. R.; Westover, L.; Xu, J. Z.; Look, R. A.; Chen, X.; Beavers, M. P.; Roberts, J.; Murray, W. V.; Demarest, K. T.; Kuo, H. Bioorg. Med. Chem. 2004, 12, 1239. doi: 10.1016/j.bmc.2003.09.047
16. [16]
  Brenet, S.; Berthiol, F.; Einhorn, J. Eur. J. Org. Chem. 2013, 8094.
17. [17]
  Paik, S.; Lee, J. Y. Tetrahedron Lett. 2006, 47, 1813. doi: 10.1016/j.tetlet.2006.01.019
18. [18]
  Brenet, S.; Baptiste, B.; Philouze, C.; Berthiol, F.; Einhorn, J. Eur. J. Org. Chem. 2013, 1041.
19. [19]
  Dubernet, M.; Caubert, V.; Guillard, J.; Claude, M.; Massuard, V. Tetrahedron. 2005, 61, 4585. doi: 10.1016/j.tet.2005.03.016
20. [20]
  Wuts. P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, John Wiley & Sons, New Jersey, 2007, p. 905.
21. [21]
  Akiyama, T.; Takesue, Y.; Kumegawa, M.; Nishimoto, H.; Ozaki, S. Bull. Chem. Soc. Jpn. 1991, 64, 2266. doi: 10.1246/bcsj.64.2266
22. [22]
  Banwell, M. G.; Hamel, E.; Hockless, D. C. R.; Verdier-Pinard, P.; Willis, A. C.; Wong, D. J. Bioorg. Med. Chem. 2006, 14, 4627. doi: 10.1016/j.bmc.2006.02.018
23. [23]
  Subramanyam, C. Synth. Commun. 1995, 25, 761. doi: 10.1080/00397919508011414
24. [24]
  Zhou, X.; Liu, W. J.; Ye, J. L.; Huang, P. Q. Tetrahedron 2007, 63, 6346. doi: 10.1016/j.tet.2007.02.087
25. [25]
  Williams, R. M.; Glinka, T.; Kwast. E.; Coffman, H.; Stille, J. K. J. Am. Chem. Soc. 1990, 112, 808. doi: 10.1021/ja00158a048
26. [26]
  Kumar, M.; Kukhsana, I. K.; Saravanan, S.; Verma, S.; Jakhar, A.; Khan, N. H.; Abdi, S. H.; Bajaj, H. C. Org. Lett. 2014, 16, 2798. doi: 10.1021/ol500699c
27. [27]
  Roy, S.; Bhanja, P.; Islam, S. S.; Bhaumik, A.; Islam, S. M. Chem. Commun. 2016, 52, 1871. doi: 10.1039/C5CC08675B
28. [28]
  Goldys, A.; McErlean, C. S. P. Tetrahedron Lett. 2009, 50, 3985. doi: 10.1016/j.tetlet.2009.04.092
1. [1]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
2. [2]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
3. [3]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
4. [4]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
5. [5]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
6. [6]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
7. [7]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
8. [8]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
9. [9]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
10. [10]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
11. [11]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
12. [12]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
13. [13]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
14. [14]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
15. [15]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
16. [16]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
17. [17]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
18. [18]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
19. [19]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
20. [20]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(2415)
HTML views(167)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis of a New Class of Chiral Maleimide Derivatives with C2-Symmetry

Metrics

通讯作者: 陈斌, bchen63@163.com

Synthesis of a New Class of Chiral Maleimide Derivatives with C₂-Symmetry