Citation: Yu Shuyan, Gao Lihong, Lan Hongbing, Qian Hengyu, Yin Zhigang, Shang Yongjia. Recent Progress in the Reactions of Aurone-Derived Azadienes[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2714-2724. doi: 10.6023/cjoc202004034 shu

Recent Progress in the Reactions of Aurone-Derived Azadienes

  • Corresponding author: Yu Shuyan, yushuyan_zzuli@163.com Shang Yongjia, shyj@mail.ahnu.edu.cn
  • Received Date: 23 April 2020
    Revised Date: 16 May 2020
    Available Online: 29 May 2020

    Fund Project: Project supported by the National Natural Science Foundation of China (No. 21602207) and the Foundation of Henan Educational Committee (No. 17A150022)the Foundation of Henan Educational Committee 17A150022the National Natural Science Foundation of China 21602207

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  • Owing to the important physiological and pharmacological activities of benzofuran compounds, the exploration for efficient synthesis methods is of great value and wide application. Aurone-derived azadienes have been identified to be effective reactants in the field of organic synthesis owing to the driving force of aromatization. A large number of reactions based on 1, 4-conjugate addition and tandem cyclization have been reported, which exhibited great advantages in the construction of heterocycles with benzofuran skeletons. In this paper, the recent progress in the chemical transformations of aurone-derived azadienens is reviewed, with emphasis on the employed catalytic system and the plausible mechanism of some reactions.
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    1. [1]

      Galal, S. A.; El-All, A. S. A.; Abdallah, M. M.; El-Diwani, H. I. Bioorg. Med. Chem. Lett. 2009, 19, 2420.
      (b) Shamsuzzaman, H. K. Eur. J. Med. Chem. 2015, 97, 483.
      (c) Radadiya, A.; Shah, A. Eur. J. Med. Chem. 2015, 97, 356.
      (d) Hiremathad, A.; Patil, M. R.; Chethana, K. R.; Chand, K.; Santos, M. A.; Keri, R. S. RSC Adv. 2015, 5, 96809.

    2. [2]

    3. [3]

      Gu, Z.; Zhou, J.; Jiang, G. F.; Zhou, Y. G. Org. Chem. Front. 2018, 5, 1148.  doi: 10.1039/C7QO01158J

    4. [4]

      Logusch, E. W.; Walker, D. M.; McDonaldand, J. F.; Franz, J. E. Biochemistry 1990, 29, 366.  doi: 10.1021/bi00454a009

    5. [5]

      Dunbar, K. L.; Scharf, D. H.; Litomska, A.; Hertweck, C. Chem. Rev. 2017, 117, 5521.  doi: 10.1021/acs.chemrev.6b00697

    6. [6]

      Zhou, Y. G.; Jiang, G. F.; Xie, J. J.; Gu, Z. Asian J. Org. Chem. 2018, 7, 1561.  doi: 10.1002/ajoc.201800299

    7. [7]

      Roethle, P. A.; Trauner, D. Nat. Prod. Rep. 2008, 25, 298.  doi: 10.1039/b705660p

    8. [8]

      Cui, H. L.; Huang, J. R.; Lei, J.; Wang, Z. F.; Chen, S.; Wu, L.; Chen, C. Y. Org. Lett. 2010, 12, 720.  doi: 10.1021/ol100014m

    9. [9]

      Lin, W.; Lin, X.; Cheng, Y. Y.; Chang, X. Y.; Zhou, S.; Li, P. F.; Li. W. J. Org. Chem. Front. 2019, 6, 2452.  doi: 10.1039/C9QO00597H

    10. [10]

      Li. W. J.; Lin, W.; Zhang, C.; Xu, W.; Cheng, Y. Y.; Li, P. F. Adv. Synth. Catal. 2019, 361, 476.  doi: 10.1002/adsc.201801422

    11. [11]

      Nair, V.; Thomas, S.; Mathew, S. C.; Abhilash, K. G. Tetrahedron 2006, 62, 6731.  doi: 10.1016/j.tet.2006.04.081

    12. [12]

      Xie, H. P.; Wu, B.; Wang, X. W.; Zhou, Y. G. Chin. J. Catal. 2019, 40, 1566.  doi: 10.1016/S1872-2067(19)63396-6

    13. [13]

      (a) Terada, M. Chem. Commun. 2008, 35, 4097.
      (b) Terada, M. Synthesis 2010, 1929.
      (c) Zamfir, A.; Schenker, S.; Freund, M.; Tsogoeva, S. B. Org. Biomol. Chem. 2010, 8, 5262.

    14. [14]

      Wang, C. J.; Yang, Q. Q.; Wang, M. X.; Shang, Y. H.; Tong, X. Y.; Deng, Y. H.; Shao, Z. H. Org. Chem. Front. 2020, 7, 609.  doi: 10.1039/C9QO01391A

    15. [15]

      (a) Saracoglu, N. Top. Heterocycl. Chem. 2007, 11, 145.
      (b) Kong, D.; Xue, T.; Guo, B.; Cheng, J.; Liu, S.; Wei, J.; Lu, Z.; Liu, H.; Gong, G.; Lan, T.; Hu, W.; Yang, Y. J. Med. Chem. 2019, 62, 3088.

    16. [16]

      Wang, C. S.; Li, T. Z.; Chen, Y. C.; Zhou, J.; Mei, G. J.; Shi, F. J. Org. Chem. 2019, 84, 3214.  doi: 10.1021/acs.joc.8b03004

    17. [17]

      (a) Khan, I. A.; Kulkarni, M. V.; Gopal, M.; Shahabuddin, M. S.; Sun, C. M. Bioorg. Med. Chem. Lett. 2005, 15, 3584.
      (b) Voigt, B.; Meijer, L.; Lozach, O.; Schä chtele, C.; Totzke, F.; Hilgeroth, A. Bioorg. Med. Chem. Lett. 2005, 15, 823.

    18. [18]

      Zeng, R.; Shan, C. Y.; Liu, M.; Jiang, K.; Ye, Y.; Liu, T. Y.; Chen, Y. C. Org. Lett. 2019, 21, 2312.  doi: 10.1021/acs.orglett.9b00598

    19. [19]

      Rong, Z. Q.; Wang, M.; Hao, C.; Chow, E.; Zhao, Y. Chem.-Eur. J. 2016, 22, 9483.  doi: 10.1002/chem.201601626

    20. [20]

      Gu, Z.; Wu, B.; Jiang, G. F.; Zhou, Y. G. Chin. J. Chem. 2018, 36, 1130.  doi: 10.1002/cjoc.201800330

    21. [21]

      Li, X. P.; Yan, J. Z.; Qin, J. L.; Lin, S. L.; Chen, W. W.; Zhan, R. T.; Huang, H. C. J. Org. Chem. 2019, 84, 8035.  doi: 10.1021/acs.joc.9b00911

    22. [22]

      Chen, J. L.; Jia, P. H.; Huang, Y. Org. Lett. 2018, 20, 6715.  doi: 10.1021/acs.orglett.8b02810

    23. [23]

      Allen, A. D.; Tidwell, T. T. Chem. Rev. 2013, 113, 7287.  doi: 10.1021/cr3005263

    24. [24]

      Bernardim, B.; Hardman-Baldwin, A. M.; Burtoloso, A. C. B. RSC Adv. 2015, 5, 13311.  doi: 10.1039/C4RA15670F

    25. [25]

      Tan, T.; Zhang, Z. J.; Zhang, Y. C.; Song, J. Org. Lett. 2019, 21, 7897.  doi: 10.1021/acs.orglett.9b02892

    26. [26]

      Xie, H. P.; Sun, L.; Wu, B.; Zhou, Y. G. J. Org. Chem. 2019, 84, 15498.  doi: 10.1021/acs.joc.9b02512

    27. [27]

      (a) Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry, Higher Education Press, Beijing, 2009.
      (b) Tomasi, S.; Renault, J.; Martin, B.; Duhieu, S.; Cerec, V.; LeRoch, M.; Uriac, P.; Delcros, J. G. J. Med. Chem. 2010, 53, 7647.
      (c) Freidinger, R. M. J. Med. Chem. 2003, 46, 5553.
      (d) Pegoraro, S.; Lang, M.; Dreker, T.; Kraus, J.; Hamm, S.; Meere, C.; Feurle, J.; Tasler, S.; Prütting, S.; Kura, Z.; Visan, V.; Grissmer, S. Bioorg. Med. Chem. Lett. 2009, 19, 2299.

    28. [28]

      (a) Xie, P.; Huang, Y. Org. Biomol. Chem. 2015, 13, 8578.
      (b) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927.
      (c) Zhao, Q. Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724.
      (d) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.

    29. [29]

      Chen, J. L.; Huang, Y. Org. Lett. 2017, 19, 5609.  doi: 10.1021/acs.orglett.7b02742

    30. [30]

      (a) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
      (b) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485.
      (c) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511.
      (d) Grossmann, D. A.; Enders, D. Angew. Chem.. Int. Ed. 2012, 51, 314.

    31. [31]

      Gao, Z. H.; Chen, K. Q.; Zhang, Y.; Kong, L. M.; Li, Y.; Ye, S. J. Org. Chem. 2018, 83, 15225.  doi: 10.1021/acs.joc.8b02497

    32. [32]

      Chen, K. Q.; Gao, Z. H.; Ye, S. Org. Chem. Front. 2019, 6, 405.  doi: 10.1039/C8QO01302K

    33. [33]

      (a) Trost, B. M. Angew. Chem.. Int. Ed. 1986, 25, 1.
      (b) Trost, B. M. Pure Appl. Chem. 1988, 60, 1615.

    34. [34]

      Shintani, R.; Park, S.; Duan, W. L.; Hayashi, T. Angew. Chem.. Int. Ed. 2007, 46, 5901.  doi: 10.1002/anie.200701529

    35. [35]

      Trost, B. M.; Zuo, Z. J. Angew. Chem.. Int. Ed. 2020, 59, 1243.  doi: 10.1002/anie.201911537

    36. [36]

      (a) Hussain, A.; Yousuf, S. K.; Mukherjee, D. RSC Adv. 2014, 4, 43241.
      (b) Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251.
      (c) Mallinson, J.; Collins, I. Future Med. Chem. 2012, 4, 1409.
      (d) Brown, H. C.; Fletcher, R. S.; Johannesen, R. B. J. Am. Chem. Soc. 1951, 73, 212.
      (e) Prelog, V. Pure Appl. Chem. 1963, 6, 545.

    37. [37]

      Ni, H. Z.; Tang, X. D.; Zheng, W. R.; Yao, W. J.; Ullah, N.; Lu, Y. X. Angew. Chem.. Int. Ed. 2017, 56, 14222.  doi: 10.1002/anie.201707183

    38. [38]

      (a) Evans, A. E.; Farber, S.; Brunet, S.; Mariano, P. J. Cancer 1963, 16, 1302.
      (b) Armstrong, J. G.; Dyke, R. W.; Fouts, P. J. Science 1964, 143, 703.
      (c) Shimokawa, T.; Kinjo, J.; Yamahara, J.; Yamasaki, M.; Nohara, T. Chem. Pharm. Bull. 1985, 33, 3545.

    39. [39]

      Yang, L. C.; Rong, Z. Q.; Wang, Y. N.; Tan, Z. Y.; Wang, M.; Zhao, Y. Angew. Chem.. Int. Ed. 2017, 56, 2927.  doi: 10.1002/anie.201611474

    40. [40]

      Rong, Z. Q.; Yang, L. C.; Liu, S.; Yu, Z. Y.; Wang, Y. N.; Tan, Z. Y.; Huang, R. Z.; Lan, Y.; Zhao, Y. J. Am. Chem. Soc. 2017, 139, 15304.  doi: 10.1021/jacs.7b09161

    41. [41]

      Wang, Y. N.; Yang, L. C.; Rong, Z. Q.; Liu, T. L.; Liu, R. Y.; Zhao, Y. Angew. Chem.. Int. Ed. 2018, 57, 1596.  doi: 10.1002/anie.201711648

    42. [42]

      (a) Lee, S. H.; Seo, H. J.; Lee, S. H.; Jung, M. E.; Park, J. H.; Park, H. J.; Yoo, J.; Yun, H.; Na, J.; Kang, S. Y.; Song, K. S.; Kim, M.; Chang, C. H.; Kim, J.; Lee, J. J. Med. Chem. 2008, 51, 7216.
      (b) Bilich, A.; Winther, M. D. Chem. Abstr. 2008, 149, 556638.
      (c) Barnes-Seeman, D.; Jain, M.; Bell, L.; Ferreira, S.; Cohen, S.; Chen, X. H.; Amin, J.; Snodgrass, B.; Hatsis, P. ACS Med. Chem. Lett. 2013, 4, 514.
      (d) Bezençon, O.; Heidmann, B.; Siegrist, R.; Stamm, S.; Richard, S.; Pozzi, D.; Corminboeuf, O.; Roch, C.; Kessler, M.; Ertel, E. A.; Reymond, I.; Pfeifer, T.; de Kanter, R.; Toeroek-Schafroth, M.; Moccia, L. G.; Mawet, J.; Moon, R.; Rey, M.; Capeleto, B.; Fournier, E. J. Med. Chem. 2017, 60, 9769.

    43. [43]

      Bos, M.; Poisson, T.; Pannecoucke, X.; Charette, A. B.; Jubault, P. Eur. J. Chem. 2017, 23, 495.

    44. [44]

      Chen, T.; Zhang, Y.; Fu, Z. Q.; Huang, W. Asian J. Org. Chem. 2019, 8, 2175.  doi: 10.1002/ajoc.201900651

    45. [45]

      Marques, A. S.; Duhail, T.; Marrot, J.; Chataigner, I.; Coeffard, V.; Vincent, G.; Moreau, X. Angew. Chem.. Int. Ed. 2019, 58, 9969.  doi: 10.1002/anie.201903860

    46. [46]

      Qi, J. F.; Tang, H. B.; Chen, C. W.; Cui, S. L.; Xu, G. Org. Chem. Front. 2019, 6, 2760.  doi: 10.1039/C9QO00653B

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