Citation: Zhao Yucheng, Xiao Qiang, Wang Baoqu, Lin Jun, Yan Shengjiao. Synthesis of Iminopyrrolone Compounds[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2690-2696. doi: 10.6023/cjoc201705004 shu

Synthesis of Iminopyrrolone Compounds

  • Corresponding author: Lin Jun, linjun@ynu.edu.cn Yan Shengjiao, yansj@ynu.edu.cn
  • Received Date: 2 May 2017
    Revised Date: 16 June 2017
    Available Online: 23 October 2017

    Fund Project: the Talent Found in Yunnan Province 2012HB001the National Natural Science Foundation of China 21362042the National Natural Science Foundation of China 21262042the Donglu Scholar of Yunnan University and the Excellent Young Talents in Yunnan University XT412003the National Natural Science Foundation of China U1202221the National Natural Science Foundation of China 21662042the Natural Science Foundation of Yunnan Province 2017FA003Project supported by the National Natural Science Foundation of China (Nos. 21362042, 21662042, U1202221, 21262042), the Natural Science Foundation of Yunnan Province (No. 2017FA003), the Talent Found in Yunnan Province (No. 2012HB001), the Donglu Scholar of Yunnan University and the Excellent Young Talents in Yunnan University (No. XT412003)

Figures(4)

  • The method was constructed for synthesis of pyrrolone compounds, which was based on the reaction of 1, 1-endiamine (1) with maleic anhydride (2) in 1, 4-dioxane at reflux in alkali condition (Et3N). As a result, a series of iminopyrrolone compounds have been synthesized by this reaction. This protocol possesses some advantages including readily available starting materials, simple operation and concise synthetic route and so on.
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    1. [1]

      (a) Cramer, N.; Buchweiz, M.; Laschat, S.; Frey, W.; Baro, A.; Mathieu, D.; Richter, C.; Schwalbe, H. Chem.-Eur. J. 2006, 12, 2448.
      (b) Cramer, N.; Laschat, S.; Baro, A.; Sehwalbe, H.; Richter, C. Angew. Chem., lnt. Ed. 2005, 44, 820.
      (c) Yoshinari, T.; Ohmori, K.; Schrems, M. G.; Pfaltz, A.; Suzuki, K. Angew. Chem., lnt. Ed. 2009, 48, 1.

    2. [2]

      Ondeyka, J.; Harris, G.; Zink, D.; Basilio, A.; Vicente, F.; Bills, G.; Collado, J.; Singh, S. B. J. Nat. Prod. 2009, 72, 136.  doi: 10.1021/np800511r

    3. [3]

      (a) Lin, Z. J.; Lu, Z. Y.; Zhu, T. J.; Fang, Y. C.; Gu, Q. Q.; Zhu, W. M. Chem. Pharm. Bull. 2008, 56, 217.
      (b) Sugie, Y.; Dekker, K. A.; Inagaki, T.; Kim, Y. J.; Sakakibara, J. A.; Kojima, Y. J. Antibiot. 2002, 55, 19.
      (c) Heiiwig, V.; Grothe, T.; Bartschmid, A. M.; Endermann, R.; Geschke, F.; Henkei, T.; Stadler, M. J. Antibiot. 2002, 55, 881.

    4. [4]

      (a) Wang, C. Y.; Wang, B. G.; Wiyowidagdo, S.; Wray, V.; Soest, R. V.; Steube, K. G.; Guan, H. S.; Proksch, P.; Ebel, R. J. Nat. Prod. 2003, 66, 51.
      (b) Vangun, H. V. K.; Hertweck, C. Org. Biomol. Chem. 2007, 5, 1702.
      (c) Vinale, F.; Flematti, G.; Sivasithamparam, K.; Lorito, M.; Marra, R.; Skelton, B.; Ghisalberti, E. L. J. Nat. Prod. 2009, 72, 2032.
      (d) Li, j.; Liu, S.; Niu, S.; Zhuang, W.; Che, Y. J. Nat. Prod. 2009, 72, 2184.

    5. [5]

      Regueiro-Ren, A.; Xue, Q.-M.; Swidorski, J. J.; Gong, Y.-F.; Mathew, M.; Parker, D. D.; Yang, Z.; Eggers, B.; D'Arienzo, C.; Sun, Y.-N.; Malinowski, J.; Gao, Q.; Wu, D.-D.; Langley, D. R.; Colonno, R. J.; Chien, C.; Grasela, D. M.; Zheng, M.; Lin, P.-F.; Meanwell, N. A.; Kadow, J. F. J. Med. Chem. 2013, 56, 1656.  doi: 10.1021/jm3016377

    6. [6]

      (a) Takeo, S.; Hayashi, H.; Miyake, K.; Takagi, K.; Tadokoro, M.; Takagi, N. Br. J. Pharmacol. 1997, 121, 477.
      (b) Oyaizu, M.; Narahashi, T. Brain Res. 1999, 822, 72.

    7. [7]

      (a) Royles, B. J. L. Chem. Rev. 1995, 95, 1981.
      (b) Schobert, R.; Schlenk, A. Bioorg. Med. Chem. 2008, 16, 4203.

    8. [8]

      Graupner, P.; Carr, A.; Clancy, E.; Gilbert, J.; Bailey, K. L.; Derby, J. A.; Gerwick, B. C. J. Nat. Prod. 2003, 66, 1558.  doi: 10.1021/np030193e

    9. [9]

      Hardy, J.; Allsop, D. Trends Pharmacol. Sci. 1991, 12, 383.  doi: 10.1016/0165-6147(91)90609-V

    10. [10]

      (a) Ramana, C. V.; Mondal, M. A.; Paranic, V. G.; Gurjar, M. K. Tetrahedron Lett. 2006, 47, 4061.
      (b) Marquardt, U.; Schmid, D.; Jung, G. Synlett 2000, 1131.

    11. [11]

      Zhuang, C.; Miao, Z.; Zhu, L.; Dong, G.; Guo, Z.; Wang, S.; Zhang, Y.; Wu, Y.; Yao, J.; Sheng C.; Zhang, W. J. Med. Chem. 2012, 22, 9630.

    12. [12]

      Shorvon, S. Lancet 2001, 358, 1885.  doi: 10.1016/S0140-6736(01)06890-8

    13. [13]

    14. [14]

    15. [15]

      (a) Wang, M.-X.; Huang, Z.-T. J. Org. Chem. 1995, 60, 2807.
      (b) Volodymyr, A. S.; Andriy, V. B.; Alexander, Y. P.; Mykhaylo, V. V. Synthesis 2007, 835.

    16. [16]

    17. [17]

      (a) Hubert, M.; Reinhard, T. Arch. Pharm. 1986, 319, 161.
      (b) Hubert, M.; Reinhard, T. Arch. Pharm. 1987, 320, 1143.

    18. [18]

      Jiang, X.-Y.; Liu, Z.-C.; Fang, L.; Yang, S.-J.; Lin, J. RSC Adv. 2014, 4, 26389.  doi: 10.1039/C4RA02519A

    19. [19]

    20. [20]

    21. [21]

      (a) Meziane, M. A.; Rahmouni, M.; Bazureau, J. P.; Hamelin, J. Synthesis 1998, 967.
      (b) Dahmani, Z. M.; Rahmouni, R.; Brugidou, J. P.; Bazureau, J. Tetrahedron Lett. 1998, 39, 8453.
      (c) Schafer, H.; Gruner, M.; Grobmann, G.; Gewald, K. Monatsh. Chem. 1991, 122, 959.

    22. [22]

      Papmeyer, M.; Vuilleumier, C. A.; Pavan, G. M.; Zhurov, K. O.; Severin, K. Angew. Chem., Int. Ed. 2016, 55, 1685.  doi: 10.1002/anie.201510423

    23. [23]

      Schirok, H.; Alonso-Alija, C.; Benet-Buchholz, J.; Goeller, A. H.; Grosser, R.; Michels, M.; Paulsen, H. J. Org. Chem. 2005, 70, 9463.  doi: 10.1021/jo0515428

    24. [24]

      (a) Kelly-Rowley, A. M.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 1995, 117, 3438.
      (b) Kelly-Rowley, A. M.; Cabell, L. A.; Anslyn, E. V. J. Am. Chem. Soc. 1991, 113, 9687.
      (c) Alizadeh, A.; Zarei, A.; Rezvanian, A. Synthesis 2011, 497.

    25. [25]

      (a) Maryamabadi, A.; Hasaninejad, A.; Nowrouzi, N.; Mohbbi, G.; Asghari, B. Bioorg. Med. Chem. 2016, 24, 1408.
      (b) Maryamabadi, A.; Hasaninejad, A.; Nowrouzi, N.; Mohebbi, G. Bioorg. Med. Chem. 2017, 25, 2507.

    26. [26]

      Silva, R. C.; Silva, P. G.; Sangi, D. P.; Pontes, J. G.; Ferreira, A. G.; Corrêa, A. G.; Paixão, M. W. Tetrahedron 2013, 69, 9007.  doi: 10.1016/j.tet.2013.08.040

    27. [27]

      Liu, J.; Zhang, H.-R.; Lin, X.-R.; Yan, S.-J.; Lin, J. RSC. Adv. 2014, 4, 27582.  doi: 10.1039/C4RA03863K

    28. [28]

      Safron, S. A.; King, G. A.; Horvat, R. C. J. Am. Chem. Soc. 1981, 103, 6333.  doi: 10.1021/ja00411a012

    29. [29]

      (a) Cassani, C.; Bergonzini, G.; Wallentin, C.-J. Org. Lett. 2014, 16, 4228.
      (b) Tanner, D. D.; Osman, S. A. A. J. Org. Chem. 1987, 21, 4689.

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