Citation: Luo Dayun, Cui Shisheng, Hu Xingmei, Lin Jun, Yan Shengjiao. Synthesis of Amide Class Heterocyclic Ketene Aminals[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 166-175. doi: 10.6023/cjoc201607002 shu

Synthesis of Amide Class Heterocyclic Ketene Aminals

  • Corresponding author: Lin Jun, linjun@ynu.edu.cn Yan Shengjiao, yansj@ynu.edu.cn
  • Received Date: 2 July 2016
    Revised Date: 25 August 2016

    Fund Project: the National Natural Science Foundation of China U1202221the National Natural Science Foundation of China 21662042the National Natural Science Foundation of China 21362042the Talent Found in Yunnan Province 2012HB001the Excellent Young Talents, Yunnan University XT412003

Figures(4)

  • In this paper, a concise protocol for synthesis of possess potential pharmacological active amide class heterocyclic ketene aminals (HKAs) has been developed, which based on the six or seven-membered HKAs 1~2, using aryl isocyanate 4 as acylation agent.The regioselective acylation reaction of HKAs in 1, 4-dioxane at room temperature gave compounds 5~6 with 90%~98% yields.However, the five-membered HKAs 3 and aryl isocyanate 4 reacted in 1, 4-dioxane catalyzed by Cs2CO3 at room temperature to obtain compounds 7 in 78%~93% yields.
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    1. [1]

      (a) Batra, S.; Tusi, Z.; Madappaa, S. Curr. Med. Chem.:An-ti-Infect. Agents 2006, 5, 135.
      (b) He, X.; Zhong, M.; Yang, J.; Wu, Z.; Xiao, Y.; Guo, H.; Hu, X. Chem. Biol. Drug Des. 2012, 79, 771.
      (c) Li, H.-Q.; Zhu, T.-T.; Yan, T.; Luo, Y.; Zhu, H.-L. Eur. J. Med. Chem. 2009, 44, 453.

    2. [2]

    3. [3]

    4. [4]

    5. [5]

      (a) Fabio, R. D.; Griffante, C.; Alvaro, G.; Pentassuglia, G.; Pizzi, D. A.; Donati, D.; Rossi, T.; Guercio, G.; Mattioli, M.; Cimarosti, Z.; Marchioro, C.; Provera, S.; Zonzini, L.; Montanari, D.; Melotto, S.; Gerrard, P. A.; Trist, D. G.; Ratti, E.; Corsi, M. J. Med. Chem. 2009, 52, 3238.
      (b) Cao, P.; Huang, X.-F.; Ding, H.; Ge, H.-M.; Li, H.-Q.; Ruan, B.-F.; Zhu, H.-L. Chem. Biodiversity 2007, 4, 881.
      (c) Debnath, A. K. J. Med. Chem. 1999, 42, 249.
      (d) Zhang, X.; Rodrigues, J.; Evans, L.; Hinkle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420.

    6. [6]

      Loto, R. T.; Loto, C. A.; Popoola, A. P. I. J. Mater. Environ. Sci. 2012, 3, 885.
       

    7. [7]

      Bucha, H. C.; Todd, C. W. Science 1951, 114, 493.

    8. [8]

      Bigi, F.; Maggi, R.; Sartori, G.; Zambonin, E. Chem. Commun. 1998, 4, 513.
       

    9. [9]

    10. [10]

    11. [11]

      (a) Yu, F.-C.; Yan, S.-J.; Hu, L.; Wang, Y.-C.; Lin, J. Org. Lett. 2011, 13, 4782.
      (b) Yu, F.-C.; Hao, X.-P.; Lin, X.-R.; Yan, S.-J.; Lin, J. Tetra-hedron 2015, 71, 4084.
      (c) Li, M.; Zhou, Z.-M.; Wen, L.-R.; Qiu, Z.-X. J. Org. Chem. 2011, 76, 3054.
      (d) Wen, L.-R.; Li, Z.-R.; Li, M.; Cao, H. Green Chem. 2012, 14, 707.
      (e) Wen, L.-R.; Sun, Q.-C.; Zhang, H.-L.; Li, M. Org. Biomol. Chem. 2013, 11, 781.

    12. [12]

      (a) Huang, C.; Yan, S.-J.; Zeng, X.-H.; Dai, X.-Y.; Zhang, Y.; Qing, C.; Lin, J. Eur. J. Med. Chem. 2011, 46, 1172.
      (b) Yan, S.-J.; Liu, Y.-J.; Chen, Y.-L.; Liu, L.; Lin, J. Bioorg. Med. Chem. Lett. 2010, 20, 5225.
      (c) Yan, S.-J.; Huang, C.; Zeng, X.-H.; Huang, R.; Lin, J. Bioorg. Med. Chem. Lett. 2010, 20, 48.

    13. [13]

      (a) Chen, N.; Meng, X.; Zhu, F.; Cheng, J.; Shao, X.; Li, Z. J. Agric. Food Chem. 2015, 63, 1360.
      (b) Shao, X.; Fu, H.; Xu, X.; Xu, X.; Liu, Z.; Li, Z.; Qian, X. J. Agric. Food Chem. 2010, 58, 2696.

    14. [14]

      Maryanoff, B. E.; Nortey, S. O.; McNally, J. J.; Sanfilippo, P. J.; McComsey, D. F.; Dubinsky, B.; Shank, R. P.; Reitz, A. B. Biomed. Chem. Lett. 1999, 9, 1547.  doi: 10.1016/S0960-894X(99)00240-1

    15. [15]

      Abdelhalim, M. M.; El-Saidi, M. M. T.; Rabie, S. T.; Elmegeed, G. A. Steroids 2007, 72, 459.  doi: 10.1016/j.steroids.2007.01.003

    16. [16]

      Wang, M.-X.; Huang, Z.-T. J. Org. Chem. 1995, 60, 2807.  doi: 10.1021/jo00114a033

    17. [17]

    18. [18]

      Yu, C.-Y.; Yan, S.-J.; Zhang, T.; Huang, Z.-T. CN 101041660, 2007[Chem. Abstr. 2007, 147, 469361].

    19. [19]

      Liu, B.; Wang, M.-X.; Huang, Z.-T. Synth. Commun. 1999, 29, 4241.  doi: 10.1080/00397919908085897

    20. [20]

      Baum, K.; Nguyen, N. V.; Gilardi, R.; Flippen-Anderson, J. L.; George, C. J. Org. Chem. 1992, 57, 3026.  doi: 10.1021/jo00037a015

    21. [21]

      Jiang, X.-Y.; Liu, Z.-C.; Fang, L.; Yang, S.-J.; Lin, J. RSC Adv. 2014, 4, 26389.  doi: 10.1039/c4ra02519a

    22. [22]

    23. [23]

      Wan, J.-P.; Gan, S.-F.; Sun, G.-L.; Pan, Y.-J. J. Org. Chem. 2009, 74, 2862.  doi: 10.1021/jo900068z

    24. [24]

      Wan, J.-P.; Lin, Y.; Jing, Y.; Xu, M.; Liu, Y. Tetrahedron 2014, 70, 7874.  doi: 10.1016/j.tet.2014.09.002

    25. [25]

      Cao, S.; Xin, L.; Liu, Y.; Wan, J.-P.; Wen, C. RSC Adv. 2015, 5, 27372.  doi: 10.1039/C5RA01901J

    26. [26]

      (a) Huang, Z.-T.; Wang, M.-X. Synthesis 1992, 1273.
      (b) Li, Z.-J.; Charles, D. Synth. Commun. 2001, 31, 527.
      (c) Chen, X.-B.; Liu, X.-M.; Huang, R.; Yan, S. J.; Lin, J. Eur. J. Org. Chem. 2013, 4607.

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