Citation: Bai Feicheng, Hu Deqing, Liu Yunyun, Wei Li. One-Pot and Multicomponent Synthesis of N-Substituted-4-hydroxyl-2-pyridones[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 2054-2059. doi: 10.6023/cjoc201801015 shu

One-Pot and Multicomponent Synthesis of N-Substituted-4-hydroxyl-2-pyridones

College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Corresponding author: Wei Li, wl@jxnu.edu.cn
Received Date: 8 January 2018
Revised Date: 21 March 2018
Available Online: 27 August 2018
Fund Project: the Department of Education of Jiangxi Province GJJ160328Project supported by the Department of Education of Jiangxi Province (No. GJJ160328) and the Doctoral Start-up Fund of Jiangxi Normal University

Figures(2)

A series of 4-hydroxyl-2-pyridone derivatives were synthesized via a one-pot and multicomponent reaction of dimethyl 3-oxopentanedioate, N, N-dimethylformamide dimethyl acetal (DMF-DMA) and primary amine in aliphatic alcohol by using L-proline as catalyst. The structures of these compounds were confirmed by NMR and HRMS. This work provides a convenient method for construction of pyridones with the advantages of operation simplicity, free of isolating intermediates etc. Moreover, the participation of solvent in the reaction enriched the diversity of 5-substitution in the pyridone backbone.
- 4-hydroxyl-2-pyridone,
- multicomponent reaction,
- dimethyl 3-oxopentanedioate,
- one-pot synthesis
1. [1]
  Tang, Y.; Li, J.; Zhao, S. Y. Chin. J. Org. Chem. 2011, 31, 9(in Chinese).
2. [2]
  Jessen, H. J.; Gademann, K. Nat. Prod. Rep. 2010, 27, 1168. doi: 10.1039/b911516c
3. [3]
  Ando, K.; Matsuura, I.; Nawata, Y.; Endo, H.; Sasaki, H.; Okytomi, T.; Saehi, T.; Tamura, G. J. Antibiot. 1978, 31, 533. doi: 10.7164/antibiotics.31.533
4. [4]
  Wat, C. K.; McInnes, A. G.; Smith, D. G.; Wright, J. L. C.; Vining, L. C. Can. J. Chem. 1997, 55, 4090.
5. [5]
  Alfatafta, A. A.; Gloer, J. B.; Scott, J. A.; Malloch, D. J. Nat. Prod. 1994, 57, 1696. doi: 10.1021/np50114a012
6. [6]
  Kohno, J.; Hirano, N.; Sugawara, K.; Nishio, M.; Hashiyama, T.; Nakanishi, N.; Komatsubara, S. Tetrahedron 2001, 57, 1731. doi: 10.1016/S0040-4020(01)00009-6
7. [7]
  Jayasinghe, L.; Abbas, H. K.; Jacob, M. R.; Herath, W. H. M. W.; Nanayakkara, N. P. D. J. Nat. Prod. 2006, 69, 439. doi: 10.1021/np050487v
8. [8]
  Zhan, J.; Burns, A. M.; Liu, M. X.; Faeth, S. H.; Gunatilaka, A. A. L. J. Nat. Prod. 2007, 70, 227. doi: 10.1021/np060394t
9. [9]
  Silva, E. D.; Geiermann, A. S.; Mitova, M. I.; Kuegler, P.; Blunt, J. W.; Cole, A. L. J.; Munro, M. H. J. Nat. Prod. 2009, 72, 477. doi: 10.1021/np800627f
10. [10]
  Tsuchinari, M.; Shimanuki, K.; Hiramatsu, F.; Muratama, T.; Koseki, T.; Shiono, Y. Z. Naturforsch., B:Chem. Sci. 2007, 62, 1203. doi: 10.1515/znb-2007-0916
11. [11]
  Hayakawa, S.; Minato, H.; Katagori, K. J. Antibiot. 1971, 24, 653. doi: 10.7164/antibiotics.24.653
12. [12]
  Matsumoto, M.; Minato, H. Tetrahedron Lett. 1976, 42, 3827.
13. [13]
  Gutierrez-Cirlos, E. B.; Merbitz-Zahradnik, T.; Trumpower, B. L. J. Biol. Chem. 2004, 279, 8708. doi: 10.1074/jbc.M311805200
14. [14]
  Bergmann, S.; Schumann, J.; Scherlach, K.; Lange, C.; Brakhage, A. A.; Hertweck, C. Nat. Chem. Biol. 2007, 3, 213. doi: 10.1038/nchembio869
15. [15]
  Wasil, Z.; Pahirulzaman, K. A. K.; Butts, C.; Simpson, T. J.; Lazarus, C. M.; Cox, R. J. Chem. Sci. 2013, 4, 3845. doi: 10.1039/c3sc51785c
16. [16]
  Fujimoto, H.; Ikeda, M.; Yamamoto, K.; Yamazaki, M. J. Nat. Prod. 1993, 56, 1268. doi: 10.1021/np50098a010
17. [17]
  Amini, S. K. J. Struct. Chem. 2015, 56, 1334. doi: 10.1134/S0022476615070148
18. [18]
  Schöffski, P. Anticancer Drugs 2004, 15, 85.
19. [19]
  Subissi, A.; Monti, D.; Togni, G.; Mailland, F. Drugs 2010, 70, 2133. doi: 10.2165/11538110-000000000-00000
20. [20]
  Schmidt, K.; Reise, U.; Li, Z.; Hamburger, M. J. Nat. Prod. 2003, 66, 378. doi: 10.1021/np020430y
21. [21]
  Cheng, Y.; Schneider, B.; Reise, U.; Schubert, B.; Li, Z.; Hamburger, M. J. Nat. Prod. 2006, 69, 436. doi: 10.1021/np050418g
22. [22]
  Zhao, S. Y.; Huang, J.; Cheng, J.; Liu, B, S.; Chen, C. Chin. J. Org. Chem. 2012, 32, 651(in Chinese).
23. [23]
  Ding, F.; Leow, M. L.; Ma, J.; William, R.; Liao, H.; Liu, X.-W. Chem.-Asian J. 2014, 9, 2548. doi: 10.1002/asia.201402466
24. [24]
  Ding, F.; William, R.; Leow, M. L.; Chai, H.; Fong, J. Z. M.; Liu, X.-W. Org. Lett. 2014, 16, 26. doi: 10.1021/ol402820d
25. [25]
  Wan, J.-P.; Gao, Y. Chem. Rec. 2016, 16, 1164. doi: 10.1002/tcr.201500296
26. [26]
  Wan, J.-P.; Zhong, S.; Guo, Y.; Wei, L. Eur. J. Org. Chem. 2017, 4401.
27. [27]
  Xu, D.-Q.; Xia, H.-B.; Luo, S.-P.; Tang, J.; Zhang, S.; Jiang, J.-R.; Xu, Z.-Y. Angew. Chem., Int. Ed. 2009, 48, 3821. doi: 10.1002/anie.v48:21
28. [28]
  Wan, J.-P.; Jing, Y.; Wei, L. Asian J. Org. Chem. 2017, 6, 666. doi: 10.1002/ajoc.v6.6
29. [29]
  Guo, Y.; Zhong, S.; Wei, L.; Wan, J.-P. Beilstein J. Org. Chem. 2017, 13, 2017. doi: 10.3762/bjoc.13.199
30. [30]
  List, B. Acc. Chem. Res. 2004, 37, 548. doi: 10.1021/ar0300571
31. [31]
  List, B.; Mukherjee, S.; Yang, J. W.; Hoffmann, S. Chem. Rev. 2007, 107, 5471. doi: 10.1021/cr0684016
32. [32]
  Notz, W.; Tanaka, F.; Barbas, C. F. Ⅲ. Acc. Chem. Res. 2004, 37, 580. doi: 10.1021/ar0300468
33. [33]
  Wang, H.; Li, L.; Lin, W.; Huang, Z.; Shi, D. Chin. J. Org. Chem. 2013, 33, 1616(in Chinese).
34. [34]
  Stanovnik, B.; Groselj, U. Adv. Heterocycl. Chem. 2010, 100, 145. doi: 10.1016/S0065-2725(10)10005-1
35. [35]
  Satheesh, M.; Balachandran, A. L.; Devi, P. R.; Deepthi, A. Synth. Commun. 2018, 48, 582. doi: 10.1080/00397911.2017.1416143
36. [36]
  Platts, M. Y.; Barber, C. G.; Chiva, J. Y.; Eastwood, R. L.; Fenwick, D. R.; Paradowski, K. A.; Blakemore, D. C. Tetrahedron Lett. 2011, 52, 512. doi: 10.1016/j.tetlet.2010.11.112
37. [37]
  Zupancic, S.; Svete, J.; Stanovnik, B. Acta Chim. Slovoca 2008, 55, 1009.
38. [38]
  Zou, J.; Zhu, L. G.; Yu, Q. S.; Lin, R. S. Chemistry 1999, (13), 2(in Chinese).
39. [39]
  Bodor, N.; Dewar, M. J. S.; Harget, A. J. J. Am. Chem. Soc. 1970, 92, 2929. doi: 10.1021/ja00713a001
40. [40]
  Schlegel, H. B. Int. J. Quantum Chem. 1982, 22, 1041. doi: 10.1002/(ISSN)1097-461X
41. [41]
  Baskovc, J.; Dahmann, G.; Golobic, A.; Groselj, U.; Kocar, D.; Stanovnik, B.; Svete, J. ACS Comb. Sci. 2012, 14, 513. doi: 10.1021/co3000709
1. [1]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
2. [2]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
3. [3]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
4. [4]
  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
5. [5]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
6. [6]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
7. [7]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
8. [8]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
9. [9]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
10. [10]
  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
11. [11]
  . . Chinese Journal of Inorganic Chemistry, 2024, 40(11): 0-0.
12. [12]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
13. [13]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
14. [14]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
15. [15]
  Yanting HUANG , Hua XIANG , Mei PAN . Construction and application of multi-component systems based on luminous copper nanoclusters. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2075-2090. doi: 10.11862/CJIC.20240196
16. [16]
  Bin HE , Hao ZHANG , Lin XU , Yanghe LIU , Feifan LANG , Jiandong PANG . Recent progress in multicomponent zirconium?based metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2041-2062. doi: 10.11862/CJIC.20240161
17. [17]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
18. [18]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
19. [19]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
20. [20]
  Yuan GAO , Yiming LIU , Chunhui WANG , Zhe HAN , Chaoyue FAN , Jie QIU . A hexanuclear cerium oxo cluster stabilized by furoate: Synthesis, structure, and remarkable ability to scavenge hydroxyl radicals. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 491-498. doi: 10.11862/CJIC.20240271

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(1626)
HTML views(127)

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