Citation: Zhao Yuying, Wang Erbing, Wang Yingli. Iodine-Promoted Three-Component Reaction of β-Keto Esters, Chalcones and Ammonium Acetate for the Synthesis of Poly-substituted Pyridines[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 866-872. doi: 10.6023/cjoc201701006 shu

Iodine-Promoted Three-Component Reaction of β-Keto Esters, Chalcones and Ammonium Acetate for the Synthesis of Poly-substituted Pyridines

  • Corresponding author: Zhao Yuying, zhaoyuyingtyust@163.com
  • Received Date: 5 January 2017
    Revised Date: 5 March 2017

    Fund Project: the Science and Technology Key Project of Shanxi Province 20130313015-2

Figures(3)

  • A three-component reaction for the synthesis of poly-substituted pyridines from β-keto esters, chalcones and ammonium acetate promoted by iodine has been reported. Advantages of the present method include ready availability of starting materials, broad scope of substrates, and convenience of operation.
  • 加载中
    1. [1]

      (a) McGrath, N. A.; Brichacek, M.; Njardarson, J. T. J. Chem. Educ. 2010, 87, 1348.
      (b) Tang, B.; Yu, F.; Li, P.; Tong, L.; Duan, X.; Xie, T.; Wang, X. J. Am. Chem. Soc. 2009, 131, 3016.
      (c) Yoo, K. S.; Park, C. P.; Yoon, C. H.; Sakaguchi, S.; O'Neil l, J.; Jung, K. W. Org. Lett. 2007, 9, 3933.

    2. [2]

      For selected reviews on the synthesis of pyridines, see: (a) Allais, C.; Grassot, J.-M.; Rodriguez, J.; Constantieux, T. Chem. Rev. 2014, 114, 10829.
      (b) Hill, M. D. Chem. Eur. J. 2010, 16, 12052.
      (c) Henry, G. D. Tetrahedron 2004, 60, 6043. For selected examples on the synthesis of pyridines, see:
      (d) Zhang, X.; Ying, W.; Wu, W.; Li, J.; Hua, J. Acta Chim. Sinica 2015, 73, 272 (in Chinese). (张晓瑜, 应伟江, 武文俊, 李晶, 花建丽, 化学学报, 2015, 73, 272.)
      (e) Shao, T.; Jiang, Z. Acta Chim. Sinica 2017, 75, 70 (in Chinese). (邵天举, 江智勇, 化学学报, 2017, 75, 70.)
      (f) Chang, L.; Lai, J.; Yuan, G. Chin. J. Chem. 2016, 34, 887. (g) Yang, F.; Sun, J.; Yan, C. Chin. J. Chem. 2015, 33, 1371.

    3. [3]

      Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223.  doi: 10.1021/cr00048a004

    4. [4]

      Chichibabin, A. E.; Zeide, O. A. J. Russ. Phys.-Chem. Soc. 1906, 37, 1229.

    5. [5]

      (a) Zecher, W.; Kröhnke, F. Chem. Ber. 1961, 94, 690.
      (b) Zecher, W.; Kröhnke, F. Chem. Ber. 1961, 94, 698.

    6. [6]

      (a) Liéby-Muller, F.; Allais, C.; Constantieux, T.; Rodriguez, J. Chem. Commun. 2008, 4207.
      (b) Allais, C.; Constantieux, T.; Rodriguez, J. Chem. Eur. J. 2009, 15, 12945.
      (c) Allais, C.; Liéby-Muller, F.; Rodriguez, J.; Constantieux, T. Eur. J. Org. Chem. 2013, 4131.
      (d) Allais, C.; Liéby-Muller, F.; Constantieux, T.; Rodriguez, J. Adv. Synth. Catal. 2012, 354, 2537.

    7. [7]

      Song, Z.; Huang, X.; Yi, W.; Zhang, W. Org. Lett. 2016, 18, 5640.  doi: 10.1021/acs.orglett.6b02883

    8. [8]

      For selected examples on the reaction catalyzed or promoted by iodine, see: (a) Ren, X.; Wang, G.; Tang, X.; Zhao, W. Chin. J. Org. Chem. 2015, 35, 1733 (in Chinese). (任相伟, 王光伟, 唐向阳, 赵温涛, 有机化学, 2015, 35, 1733.)
      (b) Wang, D.; Zhang, R.; Lin, S.; Deng, R.; Yan, Z. Chin. J. Org. Chem. 2016, 36, 2757 (in Chinese). (王丁意, 张荣兴, 林森, 邓瑞红, 严兆华, 有机化学, 2016, 36, 2757.)
      (c) Meng, T.; Chen, R.; Liu, L.; Wang, T.; Liu, X.; Zhao, W. Chin. J. Org. Chem. 2015, 35, 2108 (in Chinese). (孟团结, 陈荣祥, 刘澜涛, 王涛, 刘新明, 赵文献, 有机化学, 2015, 35, 2108.) For selected reviews on iodine, see:
      (d) Liu, D.; Lei, A. Chem. Asian J. 2015, 10, 806.
      (e) Zhao, J.; Gao, W.; Chang, H.; Li, X.; Liu, Q.; Wei, W. Chin. J. Org. Chem. 2014, 34, 1941 (in Chinese). (赵巾巾, 高文超, 常宏宏, 李兴, 刘强, 魏文珑, 有机化学, 2014, 34, 1941.)
      (f) Wu, X.; Gong, J.; Qi, X. Org. Biomol. Chem. 2014, 12, 5807.
      (g) Shen, S.; Xu, X.; Ji, S. Chin. J. Org. Chem. 2009, 29, 806 (in Chinese). (沈舒苏, 徐小平, 纪顺俊, 有机化学, 2009, 29, 806.)

    9. [9]

      (a) Gao, W.-C.; Hu, F.; Huo, Y.-M.; Chang, H.-H.; Li, X.; Wei, W.-L. Org. Lett. 2015, 17, 3914.
      (b) Gao, Q.; Liu, S.; Wu, X.; Zhang, J.; Wu, A. Org. Lett. 2015, 17, 2960.
      (c) Yan, Y.; Xu, Y.; Niu, B.; Xie, H.; Liu, Y. J. Org. Chem. 2015, 80, 5581.
      (d) Gao, Q.; Liu, S.; Wu, X.; Wu, A. Org. Lett. 2014, 16, 4582.

    10. [10]

      Zhao, Y.; Wang, E.; Wang, Y. Chin. J. Org. Chem. 2016, 36, 1681 (in Chinese).
       

    11. [11]

      For the synthesis of intermediate A, see: Stavber, G.; Iskra, J.; Zupan, M.; Stavber, S. Adv. Synth. Catal. 2008, 350, 2921. For the conversion from A to 3a, see Supporting Information.

    12. [12]

      Zhang, Q.-R.; Huang, J.-R.; Zhang, W.; Dong, L. Org. Lett. 2014, 16, 1684.  doi: 10.1021/ol500345n

    13. [13]

      Xuan, Z.; Rathwell, K.; Lee, S. Asian J. Org. Chem. 2014, 3, 1108.  doi: 10.1002/ajoc.v3.10

  • 加载中
    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]

      . . Chinese Journal of Inorganic Chemistry, 2024, 40(11): 0-0.

    3. [3]

      Chengqian Mao Yanghan Chen Haotong Bai Junru Huang Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014

    4. [4]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

    5. [5]

      Ruitong Zhang Zhiqiang Zeng Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004

    6. [6]

      Ran HUOZhaohui ZHANGXi SULong 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

    7. [7]

      Yanting HUANGHua XIANGMei 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

    8. [8]

      Bin HEHao ZHANGLin XUYanghe LIUFeifan LANGJiandong 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

    9. [9]

      Hongting Yan Aili Feng Rongxiu Zhu Lei Liu Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010

    10. [10]

      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

    11. [11]

      Zhaoyang WANGChun YANGYaoyao SongNa HANXiaomeng LIUQinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114

    12. [12]

      Xiao SANGQi LIUJianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158

    13. [13]

      Qiaowen CHANGKe ZHANGGuangying HUANGNuonan LIWeiping LIUFuquan BAICaixian YANYangyang FENGChuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311

    14. [14]

      Hongjie SHENHaozhe MIAOYuhe YANGYinghua LIDeguang HUANGXiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009

    15. [15]

      Yi DINGPeiyu LIAOJianhua JIAMingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393

    16. [16]

      Lin Ding Jinpeng Zhang Junfeng Li Daying Liu . Color Catcher: A Marvelous Encounter of Starch and Iodine. University Chemistry, 2024, 39(6): 334-341. doi: 10.3866/PKU.DXHX202311064

    17. [17]

      Yonghui ZHOURujun HUANGDongchao YAOAiwei ZHANGYuhang SUNZhujun CHENBaisong ZHUYouxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373

    18. [18]

      Liyang ZHANGDongdong YANGNing LIYuanyu YANGQi 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

    19. [19]

      Yahui HANJinjin ZHAONing RENJianjun 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

    20. [20]

      Chen LUQinlong HONGHaixia ZHANGJian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407

Metrics
  • PDF Downloads(7)
  • Abstract views(1237)
  • 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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return