Citation: Li Pengcheng, Weng Guodong, Zhang Yongdong, Zhang Xingxian. A Highly Efficient Paal-Knorr Synthesis of Chiral Pyrrole Derivatives Catalyzed by MgI2[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 364-369. doi: 10.6023/cjoc201505041 shu

A Highly Efficient Paal-Knorr Synthesis of Chiral Pyrrole Derivatives Catalyzed by MgI2

  • Corresponding author: Zhang Xingxian, 
  • Received Date: 25 May 2015
    Available Online: 17 August 2015

    Fund Project: 国家自然科学基金(Nos. 21372203,21272076) (Nos. 21372203,21272076)国家大学生创新创业计划(No. 201310337007) (No. 201310337007)浙江省新苗人才计划(No. 2014R403021)资助项目 (No. 2014R403021)

  • A novel methodology has been developed for the synthesis of N-substituted mono-pyrrole and bis-pyrrole derivatives with a chiral substituent at the nitrogen atom by MgI2-catalyzed Paal-Knorr condensation using esters of amino acids as the source of chirality. This method has some advantages such as mild reaction conditions, simple procedure, good yields, high stereoselectivity and environmental friendliness.
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    1. [1]

      [1] Demirb, A. S. Tetrahedron 2007, 63, 9746.

    2. [2]

      [2] Boger, D. L.; Boyce, C. W.; Labrili, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54;

    3. [3]

      [3] Thirumalairajan, S.; Pearce, B. M.; Thompson, A. Chem. Commun. 2010, 46, 1797.

    4. [4]

      [4] Ryzhkov, I. O.; Andreev, I. A.; Belov, G. M.; Kurkin, A. V.; Yurovskaya, M. A. Chem. Heterocycl. Compd. 2011, 47, 182.

    5. [5]

      [5] Wang, Z.-S.; Ye, H.-T. Xiao, D.; Ma, D.-S.; Gao, J.-S.; Yu, Y.-H.; Hou, G.-F.; Yan, P.-F. Chin. J. Org. Chem. 2014, 34, 2057 (in Chinese). (王子时, 叶汉韬, 肖丹, 马东升, 高金胜, 于颖慧, 侯广峰, 闫鹏飞, 有机化学, 2014, 34, 2057.)

    6. [6]

      [6] Dyatkina, N. B.; Roberts, C. D.; Keicher, J. D.; Joshua, Y. D.; Nadherny, P.; Zhang, W.; Schmitz, U.; Kongpachith, A.; Fung, K.; Novikov, A. A.; Lou, L.; Velligan, M.; Khorlin, A. A.; Chen, M. S. J. Med. Chem. 2002, 45, 805.

    7. [7]

      [7] Gupton, J. T. Top. Heterocycl. Chem. 2006, 2, 53.

    8. [8]

      [8] Dieter, R. K.; Yu, H. Org. Lett. 2000, 2, 2283.

    9. [9]

      [9] Palacios, F.; Aparico, D.; Santos, J. M.; Vicario, J. M. Tetrahedron 2001, 57, 1961.

    10. [10]

      [10] Berree, F.; Marchand, E.; Morel, G. Tetrahedron Lett. 1992, 33, 6155.

    11. [11]

      [11] Katritzky, A.; Jiang, J.; Steel, P. J. J. Org. Chem. 1994, 59, 4551.

    12. [12]

      [12] Katritzky, A.; Steel, P. J. J. Org. Chem. 1994, 59, 4551.

    13. [13]

      [13] Ramanathan, B.; Keith, A. J.; Armstrong, D.; Odom, A. L. Org. Lett. 2004, 6, 2957.

    14. [14]

      [14] Iwasawa, N.; Maeyama, K.; Saitou, M. J. Am. Chem. Soc. 1997, 119, 1486.

    15. [15]

      [15] (a) Hantzsch, A. Chem. Ber. 1890, 23, 1474. (b) Broadbent, H. S.; Burnharm, W. S.; Olsen, R. K.; Sheely, R. M. J. Heterocycl. Chem. 1968, 5, 757. (c) Bayer, H. O.; Gotthardt, H.; Huisgen, R. Chem. Ber. 1970, 103, 2356. (d) Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefter, F. C. Chem. Ber. 1970, 103, 2611. (e) Cooney, J. V.; McEwen, W. E. J. Org. Chem. 1981, 46, 2570. (f) Arcadi, A.; Rossi, E. Tetrahedron 1998, 54, 15253. (g) Periasamy, M.; Srinivas, G.; Bharati, P. J. Org. Chem. 1999, 64, 4204. (h) Srinivas, R.; Thirupathi, B.; Kumar, J. K. Prashanth; Prasad, A. N.; Reddy, B. M. Curr. Org. Chem. 2012, 16, 2482. (i) Yue, M.; Liu, J.; Wang, Y.; Yuan, B. Chin. J. Org. Chem. 2014, 34, 190 (in Chinese). (岳闽敏, 刘巨艳, 王英, 袁斌. 有机化学, 2014, 34, 190.) (j) Yuan, D.; Zeng, M.; Bai, C.; Cui, D.; Zhang, C. Chin. J. Org. Chem. 2014, 34, 1231 (in Chinese). (原东鹏, 曾明, 柏春美, 崔冬梅, 张辰, 有机化学, 2014, 34, 1231.) (k) Wu, C.; Zang, H.; Li, D.; Yu, N.; Cheng, B.; Yu, K. Chin. J. Org. Chem. 2013, 33, 2417 (in Chinese). (吴长春, 臧洪俊, 李大庆, 於年琴, 程博闻, 于楷, 有机化学, 2013, 33, 2417.)

    16. [16]

      [16] Yu, S. X.; Quesne, P. W. L. Tetrahedron Lett. 1995, 36, 6205.

    17. [17]

      [17] Rahmatpour, A. Appl. Organomet. Chem. 2011, 25, 585.

    18. [18]

      [18] Chen, J.; Wu, H.; Zheng, Z.; Jin, C.; Zhang, X.; Su, W. Tetrahedron Lett. 2006, 47, 5383.

    19. [19]

      [19] Banik, B. K.; Banik, I.; Renteria, M.; Dasgupta, S. K. Tetrahedron Lett. 2004, 45, 3417.

    20. [20]

      [20] Zhang, Z.-H.; Li, J.-J.; Li, T.-S. Ultrason. Sonochem. 2008, 15, 673.

    21. [21]

      [21] Aghapoor, K.; Ebadi-Nia, L.; Mohsenzadeh, F. J. Organomet. Chem. 2012, 708, 25.

    22. [22]

      [22] Shanthi, G.; Perumal, P. T. Tetrahedron Lett. 2009, 50, 3959.

    23. [23]

      [23] Azizi, N.; Khajeh-Amiri, A.; Ghafuri, H. Synlett 2009, 2245.

    24. [24]

      [24] Zhang, X.-X.; Li, W.-D. Chin. J. Org. Chem. 2003, 23, 1185 (in Chinese). (张兴贤, 李卫东, 有机化学, 2003, 23, 1185.)

    25. [25]

      [25] Zhang, X.-X.; Weng, G.-D.; Zhang, Y.-D.; Li, P.-C. Tetrahedron 2015, 71, 2595.

    26. [26]

      [26] Kashima, C.; Maruyama, T.; Harada, K.; Hibi, S.; Omote, Y. J. Chem. Res., Synop. 1988, 2, 62.

    27. [27]

      [27] Han, F.-G.; Lu, Y.; Ji, X.-M.; Zhao, M.-Q.; Zhang, X.-Y.; Liu, Y. Chin. J. Org. Chem. 2010, 30, 1080 (in Chinese). (韩富根, 卢叶, 姬小明, 赵铭钦, 张晓蕴, 刘云, 有机化学, 2010, 30, 1080.)

    28. [28]

      [28] Santus, R.; Patterson, L. K.; Giraud, M.; Valla, A.; Lafontant, P.; Bazin, M. Free Radical Biol. Med. 1994, 16, 801

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