Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (2): 742-750.DOI: 10.6023/cjoc202207032 Previous Articles Next Articles
王维, 张哲宇, 张雪, 于海丰*(), 罗辉, 霍东月, 徐玉澎, 赵晓波*()
收稿日期:
2022-07-25
修回日期:
2022-08-23
发布日期:
2022-09-15
基金资助:
Wei Wang, Zheyu Zhang, Xue Zhang, Haifeng Yu(), Hui Luo, Dongyue Huo, Yupeng Xu, Xiaobo Zhao()
Received:
2022-07-25
Revised:
2022-08-23
Published:
2022-09-15
Contact:
*E-mail: Supported by:
Share
Wei Wang, Zheyu Zhang, Xue Zhang, Haifeng Yu, Hui Luo, Dongyue Huo, Yupeng Xu, Xiaobo Zhao. Synthesis of Polysubstituted 2,3-Dihydropyridin-4(1H)-one in Water[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 742-750.
Entry | Molar ratio of 1a∶2a | t/oC | Time/h | Yieldb/% |
---|---|---|---|---|
1 | 1∶2 | 25 | 24 | 0 (96)c |
2 | 1∶2 | 50 | 24 | 0 (91)c |
3 | 1∶2 | 70 | 24 | 0 (88)c |
4 | 1∶2 | 80 | 24 | 18 (58)c |
5 | 1∶2 | 100 | 24 | 41 (29) c |
6 | 1∶3 | 100 | 14 | 71 |
7 | 1∶3 | 100 | 24 | 69 |
8 | 1∶4 | 100 | 12 | 70 |
9 | 1∶1 | 100 | 24 | 20 (41)c,d |
10 | 2∶1 | 100 | 24 | 6 (75)c,e |
Entry | Molar ratio of 1a∶2a | t/oC | Time/h | Yieldb/% |
---|---|---|---|---|
1 | 1∶2 | 25 | 24 | 0 (96)c |
2 | 1∶2 | 50 | 24 | 0 (91)c |
3 | 1∶2 | 70 | 24 | 0 (88)c |
4 | 1∶2 | 80 | 24 | 18 (58)c |
5 | 1∶2 | 100 | 24 | 41 (29) c |
6 | 1∶3 | 100 | 14 | 71 |
7 | 1∶3 | 100 | 24 | 69 |
8 | 1∶4 | 100 | 12 | 70 |
9 | 1∶1 | 100 | 24 | 20 (41)c,d |
10 | 2∶1 | 100 | 24 | 6 (75)c,e |
[1] |
Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302.
doi: 10.1021/cr100162c |
[2] |
Simon, M. O.; Li, C. J. Chem. Soc. Rev. 2012, 41, 1415.
doi: 10.1039/C1CS15222J |
[3] |
Kitanosono, T.; Masuda, K.; Xu, P. Y.; Kobayashi, S. Chem. Rev. 2018, 118, 679.
doi: 10.1021/acs.chemrev.7b00417 pmid: 29218984 |
[4] |
Song, H. X.; Han, Q. Y.; Zhao, C. L.; Zhang, C. P. Green Chem. 2018, 20, 1662.
doi: 10.1039/C8GC00078F |
[5] |
Cao, T. T.; Zhang, W. K.; Qin, F. H.; Kang, Q. Q.; Dong, Y. R.; Li, Q.; Kang, C.; Wei, W. T. ACS Sustainable Chem. Eng. 2020, 8, 16946.
doi: 10.1021/acssuschemeng.0c06586 |
[6] |
Sun, K.; Lv, Q. Y.; Chen, X. L.; Qu, L. B.; Yu, B. Green Chem. 2021, 23, 232.
doi: 10.1039/D0GC03447A |
[7] |
Jiang, J.; Xiao, F.; He, W. M.; Wang, L. Y. Chin. Chem. Lett. 2021, 32, 1637.
doi: 10.1016/j.cclet.2021.02.057 |
[8] |
Chattopadhyay, A. K.; Hanessian, S. Chem. Commun. 2015, 51, 16437.
doi: 10.1039/C5CC05891K |
[9] |
Chattopadhyay, A. K.; Hanessian, S. Chem. Commun. 2015, 51, 16450.
doi: 10.1039/C5CC05892A |
[10] |
Pepe, A.; Pamment, M.; Kim, Y. S.; Lee, S.; Lee, Mi. J.; Beebe, K.; Filikov, A.; Neckers, L.; Trepel, J. B.; Malhotra, S. V. J. Med. Chem. 2013, 56(21), 8280.
|
[11] |
Eiden, C. G.; Aldrich, C. C. J. Org. Chem. 2017, 82, 7806.
doi: 10.1021/acs.joc.7b00847 |
[12] |
Seki, H.; Georg, G. I. Synlett 2014, 25, 2536.
doi: 10.1055/s-0034-1378529 |
[13] |
Kim, Y. W.; Georg, G. I. Org. Lett. 2014, 16, 1574.
|
[14] |
Murphy, J. P.; Hadden, M.; Stevenson, P. J. Tetrahedron 1997, 53(34), 11827.
|
[15] |
Igarashi, E.; Sakamoto, K.; Yoshimura, T.; Matsuo, J. I. Tetrahedron Lett. 2019, 60, 13.
doi: 10.1016/j.tetlet.2018.11.040 |
[16] |
Ma, D. W.; Sun, H. Y. Org. Lett. 2000, 2, 2503.
pmid: 10956532 |
[17] |
Leflemme, N.; Dallemagne, P.; Rault, S. Synthesis 2002, 12, 1740.
|
[18] |
Yang, Y. RSC Adv. 2015, 5, 18894.
doi: 10.1039/C4RA14418J |
[19] |
Yuan, Y.; Li, X.; Ding, K. L. Org. Lett. 2002, 4, 3309.
pmid: 12227776 |
[20] |
Pégot, B.; Vo-Thanh, G. Synlett 2005, 1409.
|
[21] |
Lei, C. H.; Wang, D. X.; Zhao, L.; Zhu, J. P.; Wang, M. X. Chem.- Eur. J. 2013, 19, 16981.
doi: 10.1002/chem.201303221 |
[22] |
Obydennov, D. L.; El-Tantawy, A. I.; Sosnovskikha, V. Y. J. Org. Chem. 2018, 83, 13776.
doi: 10.1021/acs.joc.8b02075 pmid: 30336022 |
[23] |
Svetlik, J.; Kettmanna, V.; Zaleska, B. Tetrahedron Lett. 2005, 46, 5511.
doi: 10.1016/j.tetlet.2005.06.059 |
[24] |
Elias, R. S.; Saeed, B. A.; Saour, K. Y.; Al-Masoudi, N. A. Tetrahedron Lett. 2008, 49, 3049.
doi: 10.1016/j.tetlet.2008.03.064 |
[25] |
MacDonald, F. K.; Burnell, D. J. J. Org. Chem. 2009, 74, 6973.
doi: 10.1021/jo901355e pmid: 19705839 |
[26] |
Ranade, A. R.; Georg, G. I. J. Org. Chem. 2014, 79, 984.
doi: 10.1021/jo402445r |
[27] |
Niphakis, M. J.; Turunen, B. J.; Georg, G. I. J. Org. Chem. 2010, 75, 6793.
doi: 10.1021/jo100907u pmid: 20929269 |
[28] |
Gouault, N.; Roch, M. L.; Cheignon, A.; Uriac, P.; David, M. Org. Lett. 2011, 13, 437.
|
[29] |
Trinh, T. T. H.; Nguyen, K. H.; Amaral, P. A.; Gouault, N. Beilstein J. Org. Chem. 2013, 9, 2042.
doi: 10.3762/bjoc.9.242 |
[30] |
Pan, L.; Bi, X. H.; Liu, Q. Chem. Soc. Rev. 2013, 42, 1251.
doi: 10.1039/C2CS35329F |
[31] |
Pan, L.; Liu, Q. Synlett 2011, 22, 1073.
|
[32] |
Bi, X. H.; Dong, D. W.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578.
doi: 10.1021/ja043023c |
[33] |
Zhang, L.; Liang, F. S.; Cheng, X.; Liu, Q. J. Org. Chem. 2009, 74, 899.
doi: 10.1021/jo802318p pmid: 19053616 |
[34] |
Zhao, X. B.; Wang, Y. M.; Yu, H. F.; Lv, Y. C.; Jiang, S. A.; Wang, N. Tetrahedron 2021, 97, 132427.
doi: 10.1016/j.tet.2021.132427 |
[35] |
Dong, D. W.; Bi, X. H.; Liu, Q.; Cong, F. D. Chem. Commun. 2005, 3580.
|
[36] |
Gui, Q. W.; Wang, B. B.; Zhu, S.; Li, F. L.; Zhu, M. X.; Yi, M.; Yu, J. L.; Wu, Z. L.; He, W. M. Green Chem. 2021, 23, 4430.
doi: 10.1039/D1GC01017D |
[37] |
Wu, Y.; Chen, J. Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W. M. Green Chem. 2021, 23, 3950.
doi: 10.1039/D1GC00562F |
[38] |
Gui, Q.W.; Teng, F.; Li, Z. C.; Xiong, Z. Y.; Jin, X. F.; Lin, Y. W.; Cao, Z.; He, W. M. Chin. Chem. Lett. 2021, 32, 1907.
doi: 10.1016/j.cclet.2021.01.021 |
[39] |
Yu, H. F.; Liao, P. Q.; Mei, Z. M. Synthesis, 2021, 52, 2111.
doi: 10.1055/s-0040-1707999 |
[40] |
Yu, H. F.; Wang, K. H.; Zhang, X.; Wang, W. J. Synthesis 2021, 53, 1989.
doi: 10.1055/s-0040-1706658 |
[41] |
Yu, H. F.; Zhao, L. J.; Diao, Q. P.; Li, T. C.; Liao, P. Q.; Hou, D. Y.; Xin, G. Synlett 2017, 28, 1828.
doi: 10.1055/s-0036-1588982 |
[42] |
Dong, D. W.; Ouyang, Y.; Yu, H. F.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. J. Org. Chem. 2005, 70, 4535.
doi: 10.1021/jo050271y |
[43] |
Yu, H. F.; Liao, P. Q. Tetrahedron Lett. 2016, 57, 2868.
doi: 10.1016/j.tetlet.2016.05.062 |
[44] |
Qi, F.; Yu, H. F.; Wang, Y. N.; Lv, Y.; Li, Y. X.; Han, L.; Wang, R.; Feng, X. N. Synth. Commun. 2017, 47, 2220.
doi: 10.1080/00397911.2017.1368084 |
[45] |
Hu, X. Y.; Yu, H. F.; Wang, W. J.; Jiang, S. A.; Liu, Q.; He, J. Chin. J. Org. Chem. 2019, 39, 3183. (in Chinese)
doi: 10.6023/cjoc201904002 |
(胡小宇, 于海丰, 王文举, 姜思傲, 刘奇, 何洁, 有机化学, 2019, 39, 3183.)
doi: 10.6023/cjoc201904002 |
|
[46] |
Zhao, Y. H.; Yu, H. F.; Liao, P. Q.; Wang, W. J. Chem. Res. Chin. Univ. 2020, 36, 847.
doi: 10.1007/s40242-019-0011-8 |
[47] |
Zhao, X. B.; Jiang, S. A.; Wang, N.; Yu, H. F. Synth. Commun. 2020, 50, 3404.
doi: 10.1080/00397911.2020.1801747 |
[48] |
Jia, J.; Su, Y.; Yu, H. F.; Du, H. T.; Mei, Z. M. Synth. Commun. 2021, 51, 1581.
|
[49] |
Yu, H. F.; Zhang, Z. Y.; Zhang, X.; Xu, Y. P.; Huo, D. Y.; Zhang, L. Y.; Wang, W. J. J. Org. Chem. 2022, 87, 2985.
doi: 10.1021/acs.joc.1c02825 |
[50] |
CCDC 2163176 (3a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif
|
[1] | Yuyuan Liu, Yaqin Lei, Wen Yang, Wanxiang Zhao. Cobalt-Catalyzed Remote Hydroboration of Enamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1761-1771. |
[2] | Zengjin Dai, Xumu Zhang, Qin Yin. Advances on Asymmetric Reductive Amination with Ammonium Salts as Amine Sources [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2261-2274. |
[3] | Qingyun Gu, Zhenfeng Cheng, Xiaobao Zeng. Electrochemical Oxidative Trifluoromethylation of α-Oxoketene Ketene Dithioacetals with CF3SO2Na [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1537-1544. |
[4] | Yunkui Xiong, Jianye Zhang, Qun Shen, Jiayu Huang, Tao Wang. Electrochemical Coupling of the Sulfonic Acid Sodium and Tertiary Amines for the Synthesis ofβ-Amidovinyl Sulfones [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2735-2742. |
[5] | Huiming Di, Yunting Liu, Yanrong Ma, Xinyue Yang, Hui Jin, Lixin Zhang. Recent Advances in Organocatalytic Asymmetric Synthesis of 3,4-Dihydropyran-2-ones and 3,4-Dihydropyridin-2-ones [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2228-2248. |
[6] | Jinni Liu, Yibi Xie, Qingqing Yang, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2374-2383. |
[7] | Linlin Li, Xiaoyu Chen, Congcong Pei, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu. Transition Metal-Free Deuteride Reduction of N-tert-Butanesulfinyl Ketimines Derivatives via B2pin2/D2O System [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2319-2325. |
[8] | Yuan Chen, Lijing Xia, Yiting Chang, Wuzhen Ma, Bin Wang. Application of N-Alkyl Amines as Versatile Building Blocks in Oxidative Coupling Reactions [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1851-1877. |
[9] | Zhaowei Bao, Jie Lü, Zhichao Jin. Photochemical Reduction of Nitroaromatics Mediated by p-Toluenethiol/PCy3 [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4773-4779. |
[10] | Quan Gou, Qiujian Tan, Qianqiong Chen, Jianhong Tan, Kaimin Wang, Jianfeng Xie. Copper-Catalyzed Regioselective C(sp3)—H Sulfonimidization of Aliphatic Cyclic Tertiary Amines [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4459-4466. |
[11] | Zhang Yongna, Duan Hui-Xin, Wang You-Qing. Research Progress in Asymmetric Reactions of Imines Using Chiral Primary Amines as Organocatalysts [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1514-1528. |
[12] | Tang Liang, Li Xuewei, Xie Fang, Zhang Wanbin. Catalytic Kinetic Resolution of Amines and Their Derivatives by Non-acylation Reaction [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 575-588. |
[13] | Liu Xueying, Liu Zhenwei, Guo Yuanyuan, Li Jingya, Zou Dapeng, Wu Yusheng, Wu Yangjie. One-Pot, Two-Step Reductive Amination of Boronate Ester Containing Aromatic Amines and Aldehydes Using B2pin2 as Reductant [J]. Chin. J. Org. Chem., 2019, 39(7): 2001-2008. |
[14] | Dai Xuemei, Li Yanjun, Zhang Shaonan, Gong Lei. Visible-Light-Induced[3+2] Annulation of Cyclopropylamines with 1,2-Diketone Derivatives [J]. Chin. J. Org. Chem., 2019, 39(6): 1711-1719. |
[15] | Li Chun, Wang Mengna, Lu Xunhua, Yang Yuanyong, Zhang Lin. Pd-Catalyzed N-Formylation of Amines with N,N-Dimethylformamide [J]. Chin. J. Org. Chem., 2019, 39(4): 1109-1115. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||